USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 1 of 38
[PUBLISH]
In the
United States Court of Appeals
For the Eleventh Circuit
____________________
No. 21-11591
____________________
BRANDY BAIN JENNINGS,
Petitioner-Appellant,
versus
SECRETARY, FLORIDA DEPARTMENT OF CORRECTIONS,
Respondent-Appellee.
____________________
Appeal from the United States District Court
for the Middle District of Florida
D.C. Docket No. 2:13-cv-00751-SPC-MRM
____________________
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 2 of 38
2 Opinion of the Court 21-11591
Before JORDAN, BRANCH, and BRASHER, Circuit Judges.
BRANCH, Circuit Judge:
Brandy Bain Jennings is a Florida prisoner serving three
death sentences for the 1995 murders of Dorothy Siddle, Vicki
Smith, and Jason Wiggins during a robbery at the Cracker Barrel
where Jennings formerly worked. 1 After pursuing a direct appeal
and postconviction relief in the Florida state courts, Jennings filed
a federal habeas petition under
28 U.S.C. § 2254, alleging, in
relevant part, that his counsel rendered constitutionally ineffective
assistance during the penalty phase. After the district court denied
Jennings’s § 2254 petition on the merits, we granted a certificate of
appealability (“COA”) on one issue: “Whether the district court
erred in denying Jennings’s claim that his trial counsel rendered
ineffective assistance in the penalty phase of his capital trial by
failing to conduct further investigation into Jennings’s childhood
and background.”
After review and with the benefit of oral argument, we
conclude that the Florida Supreme Court’s decision that Jennings
failed to establish prejudice was not contrary to, or an
unreasonable application of, clearly established federal law, and we
affirm on that ground.
1 Jennings is also serving 15 years’ imprisonment for the robbery.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 3 of 38
21-11591 Opinion of the Court 3
I. Background
A. Guilt Phase of the Trial
In 1995, a Florida grand jury indicted Jennings and
codefendant Jason Graves with three counts of premeditated
murder and one count of robbery. 2 Public Defenders Tom Osteen
and Adam Sapenoff were appointed to represent Jennings. The
trial took place in October 1996. The Florida Supreme Court
summarized the facts of this case as follows:
Dorothy Siddle, Vicki Smith, and Jason Wiggins, all
of whom worked at the Cracker Barrel Restaurant in
Naples, were killed during an early morning robbery
of the restaurant on November 15, 1995. Upon
arriving on the scene, police found the bodies of all
three victims lying in pools of blood on the freezer
floor with their throats slashed. Victim Siddle’s hands
were bound behind her back with electrical tape;
Smith and Wiggins both had electrical tape around
their respective left wrists, but the tape appeared to
have come loose from their right wrists.
Police also found bloody shoe prints leading from the
freezer, through the kitchen, and into the office,
2 Graves was 18 years’ old at the time of the crimes, and the State agreed to
waive the death penalty in Graves’s case in exchange for his waiver of a motion
for a continuance to allow him more time to prepare for a capital trial. Graves
was convicted on all charges in a separate proceeding and sentenced to the
only available sentence—life imprisonment.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 4 of 38
4 Opinion of the Court 21-11591
blood spots in and around the kitchen sink, and an
opened office safe surrounded by plastic containers
and cash. Outside, leading away from the back of the
restaurant, police found scattered bills and coins, shoe
tracks, a Buck knife, a Buck knife case, a pair of blood-
stained gloves, and a Daisy air pistol.
Jennings (age twenty-six) and Jason Graves (age
eighteen), both of whom had previously worked at
the Cracker Barrel and knew the victims, were
apprehended and jailed approximately three weeks
later in Las Vegas, Nevada, where Jennings ultimately
made lengthy statements to Florida law enforcement
personnel. In a taped interview, Jennings blamed the
murders on Graves, but admitted his (Jennings’)
involvement in planning and, after several aborted
attempts, actually perpetrating the robbery with
Graves. Jennings acknowledged wearing gloves
during the robbery and using his Buck knife in taping
the victims’ hands, but claimed that, after doing so,
he must have set the Buck knife down somewhere
and did not remember seeing it again. Jennings
further stated that he saw the dead bodies in the
freezer and that his foot slipped in some blood, but
that he did not remember falling, getting blood on his
clothes or hands, or washing his hands in the kitchen
sink. Jennings also stated that the Daisy air pistol
belonged to Graves, and directed police to a canal
where he and Graves had thrown other evidence of
the crime.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 5 of 38
21-11591 Opinion of the Court 5
In an untaped interview the next day, during which
he was confronted with inconsistencies in his story
and the evidence against him, Jennings stated, “I think
I could have been the killer. In my mind I think I
could have killed them, but in my heart I don’t think
I could have.”
At trial, the taped interview was played for the jury,
and one of the officers testified regarding Jennings’
untaped statements made the next day. The items
ultimately recovered from the canal were also
entered into evidence.
The medical examiner, who performed autopsies on
the victims, testified that they died from “sharp force
injuries” to the neck caused by “a sharp-bladed
instrument with a very strong blade,” like the Buck
knife found at the crime scene. A forensic serologist
testified that traces of blood were found on the Buck
knife, the Buck knife case, the area around the sink,
and one of the gloves recovered from the crime
scene, but in an amount insufficient for further
analysis. An impressions expert testified that
Jennings’ tennis shoes recovered from the canal
matched the bloody shoe prints inside the restaurant
as well as some of the shoe prints from the outside
tracks leading away from the restaurant.
...
The State also presented testimony concerning
previous statements made by Jennings regarding his
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 6 of 38
6 Opinion of the Court 21-11591
dislike of victim Siddle. Specifically, Bob Evans, one
of the managers at Cracker Barrel, testified that
Jennings perceived Siddle to be holding him back at
work and that, just after Jennings quit, he said about
Siddle, “I hate her. I even hate the sound of her
voice.” Donna Howell, who also worked at Cracker
Barrel, similarly testified that she was aware of
Jennings’ animosity and dislike of Siddle, and that
Jennings had once said about Siddle, “I can’t stand the
bitch. I can’t stand the sound of her voice.”
The jury found Jennings guilty as charged.
Jennings v. State,
718 So. 2d 144, 145–47 (Fla. 1998) (footnotes
omitted).
B. The Penalty Phase
Following the jury’s guilty verdict, Jennings’s penalty phase
proceeded the very next day. The trial court instructed the jury
that its sentencing determination was an advisory
recommendation and that “[t]he final decision as to what
punishment shall be imposed rests solely with the judge.” 3 The
3 At the time of Jennings’s trial, the jury’s sentencing determination was
advisory and required only a majority vote, but the trial court was required to
place “great weight” upon the recommendation of the jury. See
Fla. Stat.
§ 921.141(2) (1996); Tedder v. State,
322 So. 2d 908, 910 (Fla. 1975) (holding
that jury recommendation “should be given great weight”), abrogated by
Hurst v. Florida,
577 U.S. 92 (2016). A vote of six or more jurors was necessary
for a recommendation of life imprisonment. State v. Steele,
921 So. 2d 538,
545 (Fla. 2005), abrogated by Hurst, 577 U.S. at 92; see also Reynolds v. State,
251 So. 3d 811, 827 (Fla. 2018) (explaining that under Florida’s former capital
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 7 of 38
21-11591 Opinion of the Court 7
trial court further instructed that under Florida law, it was
“required to give great weight and deference” to the jury’s
recommendation.
Jennings called six witnesses during the penalty phase—
Michael Lobdell, Angela Lobdell, Brian McBride, Rebecca Lloyd,
Mary Hamler, and his mother Tawny Jennings. These witnesses
all testified very positively to Jennings’s character, collectively
stating that Jennings was a good friend to everyone, a good son,
“happy-go-lucky,” “easy going,” “fun-loving,” wonderful with
children, and not a troublemaker.
On cross-examination, the State elicited testimony from
Angela and Michael Lobdell that Jennings came to their home the
day after the murder, and he was not acting any differently.
Additionally, McBride testified that the day before the robbery,
Jennings told McBride that he was working at a mall on a
construction job and that he was getting paid the next day and
sentencing scheme, a jury “had various options for recommendations,
including life, 7–to–5 death, 8–to–4 death, 9–to–3 death, 10–to–2 death, 11–to–
1 death, and unanimous death outcomes”).
Florida has since amended its capital sentencing scheme and now
requires that, in order for the jury to recommend a death sentence, the jury
must unanimously find the existence of at least one aggravating factor and
unanimously agree that the defendant should be sentenced to death.
Fla. Stat.
§ 921.141(2) (2021). However, the jury’s recommendation that the defendant
be sentenced to death is still advisory, and the trial court may override the
recommendation.
Id. § 921.141(3).
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 8 of 38
8 Opinion of the Court 21-11591
would be heading to California.
Hamler—who was in a relationship with Jennings for a
couple of years—testified on cross-examination that one time
when they were watching a news broadcast about a robbery,
Jennings stated that he “wouldn’t be stupid enough to stick
around” and that he “would go north.” She also stated that
Jennings was very angry with Cracker Barrel because it had told
him to cut off his ponytail if he wanted “to advance himself,” and
his ponytail was part of his Indian heritage. She confirmed that
Jennings cut his ponytail off and had a grudge against Cracker
Barrel because he was not promoted. Jennings held victim
Dorothy Siddle particularly responsible, and told Hamler “[o]ne
day [Siddle] would get hers.” 4
Lastly, Tawny Jennings, Jennings’s mother, testified to
Jennings’s background and the close relationship she shared with
her son. Specifically, she testified that Jennings’s father was a Sioux
Indian, and she divorced him while she was pregnant with
Jennings. Jennings never met his father. Jennings was her only
4 Siddle was an associate manager at the Cracker Barrel restaurant. During
the guilt phase of the trial, another associate manager testified that Jennings,
who was a grill cook, wanted to cross-train to become a server, but
management told him that he had some areas he needed to improve first,
including his “basic appearance, clothes, . . . [his] big long ponytail, . . . and
also his attitude.” It is unclear from the record whether Siddle was the
associate manager tasked with relaying this information to Jennings, but as a
scheduling manager, she would have been the person to schedule the desired
cross-training.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 9 of 38
21-11591 Opinion of the Court 9
living child. 5 She and Jennings moved a lot. They lived in Oregon
for the first nine years of Jennings’s life, then they moved to
Colorado (for about a year and a half), moved back to Oregon (for
six months), then moved to Wyoming (for a year), then moved
back to Oregon (for a year), then Arizona, and finally Florida when
Jennings was about 14 or 15 years’ old. Tawny was a single mom
all of Jennings’s childhood, and she occasionally had “a male
companion” that lived with them. According to Tawny, Jennings
was a straight-A student in school, but he had to quit high school
at 17 because Tawny became very ill, and he needed to care for her.
Tawny explained that she and Jennings were “very close” like “best
friends,” and that she could not have asked for a better son.
In closing, the State argued that it had established three
statutory aggravating factors:6 (1) that the murders were
5 Tawny had twins that died of crib death before Jennings was born.
6 At the time of Jennings’s trial, Florida law defined aggravating circumstances
as the following:
(a) The capital felony was committed by a person under
sentence of imprisonment or placed on community control.
(b) The defendant was previously convicted of another capital
felony or of a felony involving the use or threat of violence to
the person.
(c) The defendant knowingly created a great risk of death to
many persons.
(d) The capital felony was committed while the defendant was
engaged, or was an accomplice, in the commission of, or an
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 10 of 38
10 Opinion of the Court 21-11591
committed while Jennings engaged in or was an accomplice in the
commission of the crime of robbery;7 (2) the murders were
attempt to commit, or flight after committing or attempting
to commit, any robbery . . . .
(e) The capital felony was committed for the purpose of
avoiding or preventing a lawful arrest or effecting an escape
from custody.
(f) The capital felony was committed for pecuniary gain.
(g) The capital felony was committed to disrupt or hinder the
lawful exercise of any governmental function or the
enforcement of laws.
(h) The capital felony was especially heinous, atrocious, or
cruel.
(i) The capital felony was a homicide and was committed in a
cold, calculated, and premeditated manner without any
pretense of moral or legal justification.
(j) The victim of the capital felony was a law enforcement
officer engaged in the performance of his official duties.
(k) The victim of the capital felony was an elected or appointed
public official engaged in the performance of his official duties
if the motive for the capital felony was related, in whole or in
part, to the victim’s official capacity.
(l) The victim of the capital felony was a person less than 12
years of age.
Fla. Stat. § 921.141(5) (1996).
7 In support of this aggravator, the State emphasized that the bloody shoe
prints in the restaurant led from the freezer where the victims were to the
office where the money was located.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 11 of 38
21-11591 Opinion of the Court 11
committed for the purpose of avoiding or preventing a lawful
arrest; 8 and (3) the murders were committed in a cold, calculated,
and premeditated manner. 9
In response, Jennings’s counsel argued that the second and
third aggravator did not apply. Jennings’s counsel also argued that
the State’s contention that Jennings wanted to get revenge against
Siddle because Jennings cut off his ponytail but then did not get the
promotion was “a red herring” because Jennings and Graves did
not know who the manager would be the morning of the robbery.
8 In support of the second aggravator, the State emphasized that Jennings and
Graves wore gloves so as to not leave identifying fingerprints. The State
pointed out that they had masks with them in the truck, and Jennings admitted
in a statement to law enforcement that the initial plan had been to wear masks
and snatch the money. The State argued that they chose not to wear the
masks because they knew there was no reason to wear masks if they were
going to eliminate the witnesses. The State also pointed to the testimony from
the guilt phase that Jennings stated that if he ever committed a robbery, he
would not leave any witnesses.
9 In support of this third aggravator, the State argued that Jennings carried the
knife and killed the victims in a very personal way, one by one. The State also
emphasized that there was evidence of calculated premeditation, including
that Jennings attempted to set up an alibi; he and Graves brought tape with
them to bind the victims; they wore gloves; they hid the truck; they registered
in a hotel both before and after the crime using their own names (which
demonstrated that they were not concerned with being linked to the crime
because they knew they were not leaving any witnesses); and the day after
Jennings went to a friend’s house and was not acting any different.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 12 of 38
12 Opinion of the Court 21-11591
Finally, counsel argued that there were several mitigating
factors in Jennings’s life—“[h]is mother moved him about the
country when he was young, quite a bit”; “[h]e never received a
proper education”; “[h]e never knew his father” and “never had a
continuous father image in his home”; he was an only child
without any siblings to lean on; “[h]e had a succession of boyfriends
of his mother’s who lived in the home from time to time”; he loved
his mother and quit school to help her when she got sick; Jennings
worked and contributed positively to society; and he had friends
and people liked him. Counsel also reminded the jury that Graves
would receive a life sentence for the same offenses and begged the
jury to “show mercy” on Jennings.
The jury deliberated approximately an hour and a half and
returned a 10 to 2 recommendation in favor of the death penalty
for each of the three murder counts.
At the separate sentencing hearing, the trial court addressed
the aggravating and mitigating circumstances. First, the trial court
found the existence of the three aggravating factors proffered by
the State. Second, the trial court found one statutory mitigating
factor—Jennings had no significant prior criminal history, which it
gave some weight.10 Third, the trial court found the following
10 Florida law provided for the following statutory mitigating circumstances:
(a) The defendant has no significant history of prior criminal
activity.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 13 of 38
21-11591 Opinion of the Court 13
non-statutory mitigating circumstances: (1) Jennings had a
“deprived childhood”—he never knew his father, his father
abandoned his mother, his mother moved around frequently
during his childhood years and had several boyfriends (given some
weight); (2) Jennings’s codefendant received life imprisonment for
the same crimes based on the same evidence (given some weight);
(3) Jennings cooperated with law enforcement and made a
voluntary statement that led officers to various items of evidence
(b) The capital felony was committed while the defendant was
under the influence of extreme mental or emotional
disturbance.
(c) The victim was a participant in the defendant’s conduct or
consented to the act.
(d) The defendant was an accomplice in the capital felony
committed by another person and his participation was
relatively minor.
(e) The defendant acted under extreme duress or under the
substantial domination of another person.
(f) The capacity of the defendant to appreciate the criminality
of his conduct or to conform his conduct to the requirements
of law was substantially impaired.
(g) The age of the defendant at the time of the crime.
Fla. Stat. § 921.141(6) (1996). Jennings argued for three statutory mitigating
circumstances: (1) he had “no significant history of prior criminal activity”;
(2) he was an accomplice in the offense and his participation was relatively
minor; and (3) Jennings acted under “extreme duress or under the substantial
domination of another person.” See
Fla. Stat. § 921.141(6)(a), (b), and (e)
(1996). The trial court found that the second and third statutory mitigators
Jennings argued for did not exist.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 14 of 38
14 Opinion of the Court 21-11591
(given substantial weight); (4) Jennings had a regular, steady
employment history (given little weight); (5) Jennings had a close,
loving relationship with his mother (given little weight);
(6) Jennings had “[p]ositive personality traits enabling the
formation of strong, caring relationships with peers” (given some
weight); (7) Jennings had a “[c]apacity to care for and be mutually
loved by children” (given some weight); and (8) Jennings exhibited
“exemplary courtroom behavior” during the proceedings (given
little weight).
The trial court found that “the aggravating
circumstances . . . substantially outweigh[ed] the mitigating
circumstances present” and that death was the appropriate
sentence. Accordingly, the trial court imposed a sentence of death
for each of the three murder counts and 15 years’ imprisonment
for the robbery count.
On direct appeal, the Florida Supreme Court affirmed
Jennings’s convictions and sentences, and the United States
Supreme Court denied certiorari. Jennings,
718 So. 2d at 144, cert.
denied,
527 U.S. 1042 (1999). 11
11 The Florida Supreme Court rejected Jennings’s argument that the evidence
was insufficient to support the avoid arrest aggravator and the cold, calculated,
and premeditated aggravator. Jennings,
718 So. 2d at 150–53.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 15 of 38
21-11591 Opinion of the Court 15
C. State Postconviction Proceedings
Thereafter, Jennings, through counsel, filed a state
postconviction motion to vacate his judgment of conviction and
sentence, under Florida Rule of Criminal Procedure 3.850 and
3.851, followed by several amended motions. In relevant part, he
argued in two related claims that his counsel rendered
constitutionally ineffective assistance when he failed to adequately
investigate, prepare, and present mitigation at the penalty phase,
including failing to adequately investigate his background and
childhood, which he alleged contained a wealth of mitigation
evidence, and failed to provide background information to the
mental health experts that evaluated him prior to trial. The state
postconviction court ordered an evidentiary hearing on his claims,
at which Jennings presented several witnesses.
i. Evidentiary Hearing Testimony
As relevant to this appeal, Jennings’s trial counsel, Thomas
Osteen, who had extensive capital case experience at the time he
represented Jennings,12 testified that an investigator, a court-
appointed psychiatrist, Dr. Robert Wald, and a court-appointed
12 Osteen testified that he retired in 2000, but he had been an assistant public
defender for 30 years, and he had represented approximately 30 capital
defendants prior to representing Jennings in 1996. Osteen also testified that
co-counsel Adam Sapenoff did not play any role in the penalty phase other
than being present.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 16 of 38
16 Opinion of the Court 21-11591
psychologist, Dr. Russell Masterson, assisted him with preparation
for Jennings’s trial and the penalty phase. 13
Dr. Masterson conducted various tests on Jennings and the
results were all within normal limits. Dr. Masterson opined that
Jennings had superior intelligence, and his testing results revealed
no evidence of “psychotic process,” but “suggest[ed] the
personality disorder, characterological disorder, sociopathic type
of personality.”
With regard to Jennings’s background, Dr. Masterson noted
the following in his report: (1) Jennings and his mother moved
around Colorado, Wyoming, Oregon, and Arizona during his
childhood; (2) his mother had multiple relationships; (3) Jennings
never met his father; (4) Jennings reported being a straight-A
student, with no behavior problems; (5) Jennings “always had lots
of friends” and described his childhood as “pretty normal” and “a
13 Osteen utilized the Public Defender’s Office’s Investigator, Ed Neary, who
was a retired police investigator and assisted Osteen in “just about all of [his]
capital cases.” Although Neary did not have any formal mental health training
or expertise, Osteen believed that Neary had “a good feel” for those types of
issues. Osteen also testified that he worked regularly with both Dr. Wald and
Dr. Masterson in other cases, and that they “knew what [he] was looking for.”
Osteen did not seek assistance from a mitigation expert, which he
explained were “not prevalent” at the time of the trial. Instead, he relied on
what he learned from Dr. Wald and Dr. Masterson. Osteen did not attempt
to obtain school records, employment records, or medical records, and he did
not attempt to interview any of Jennings’s relatives other than Jennings’s
mother.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 17 of 38
21-11591 Opinion of the Court 17
pretty good first 15 years”; (6) Jennings became sexually active at
age 12 when he was seduced by an older woman he babysat for,
but he indicated his “first sexual experiences” were at age 5 or 6
with a female cousin who was age 10; (7) Jennings denied any
history of sexual abuse from adults; (8) at age 15, Jennings and his
mother moved to Florida and his life “did a 180”—Jennings did not
like the Florida school, he was bored, and he felt rejected by his
peers, and he got into drugs, alcohol, and street racing; (9) as a teen,
Jennings got into a fight with his mother’s boyfriend and
hospitalized him—the boyfriend had been drunk and attacked
Jennings’s mother; (10) Jennings dropped out of school his junior
year of high school; (11) after dropping out, he “got into bar fights
and was into acid, pot, and alcohol”; (12) he had regular
employment in various occupations; (13) in 1989 or 1990, when a
man threatened a woman Jennings was dating, Jennings kidnapped
the man, had a firearm with him, and planned to kill the man, but
he was arrested and pleaded no contest to attempted armed
robbery (he was sentenced to a year in county jail and five years’
probation); (14) while in jail, he was in “30 or 40 fights” but never
got in trouble; (15) in 1992, “his life kind of fell apart” and he got
heavy into drugs and alcohol and moved back in with his mother;
(16) in 1994, he moved in with Mary Hamler—he loved her three
kids a lot, but “really didn’t care about her”; and (17) after he and
Hamler broke up, Jennings moved in with codefendant Graves.
Dr. Wald’s report indicated that Jennings self-reported
similar information concerning his childhood, educational
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 18 of 38
18 Opinion of the Court 21-11591
history, 14 and background. 15 Jennings also reported that he saw a
psychiatrist when he was eight years’ old due to his “bad temper,”
including one instance where he choked his cousin for laughing at
him. Dr. Wald agreed with Dr. Masterson’s assessment that
Jennings’s testing was all relatively normal and opined that
Jennings was very intelligent, with no mental disorders or brain
dysfunction, and that Jennings had a “sociopathic personality.”16
After reviewing their reports, Osteen elected not to call Dr.
Wald or Dr. Masterson during the penalty phase. 17
14 Dr. Wald reviewed Jennings’s school records from Florida, noting that they
were “essentially non-contributory” to his report and indicated that Jennings
struggled with several courses.
15 Dr. Wald also noted that Jennings suffered a concussion at age 2 or 3 after
he was hit on the head by a wooden board, which resulted in his
hospitalization, and that Jennings had a lengthy history of drug and alcohol
abuse that began in his teens. Jennings had a “number of prior arrests,”
primarily for traffic violations, but including a shoplifting arrest in his teens
and his arrest on attempted armed robbery. Jennings also self-reported that
he “ha[d] stolen things for both money and . . . the ‘adrenalin[e] rush.’”
Jennings indicated that “he [sought] gratification, [did] not feel at all
remorseful about crimes he ha[d] committed, and ha[d] experienced no guilt
relative to legal infractions.”
16 Dr. Wald attempted to interview Jennings’s mother, who was very resistant
at first, and then she did not show up for the scheduled interview.
17 Osteen explained that it was part of his trial strategy not to call Dr. Wald or
Dr. Masterson as witnesses because, after speaking with them, he “came to
the conclusion that [their testimony] would not be helpful to a great extent,
and so [he] decided to rely on [Jennings’s] mother and his friends to come
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 19 of 38
21-11591 Opinion of the Court 19
In addition to Osteen’s testimony, at the state
postconviction evidentiary hearing, Jennings presented testimony
from three experts in support of his claims—Dr. Thomas Hyde, a
behavioral neurologist, Dr. Hyman Eisenstein, a clinical
psychologist and expert in neuropsychology, and Dr. Faye Sultan,
a clinical psychologist. Dr. Hyde and Dr. Eisenstein both testified
that Jennings suffered a number of closed head injuries 18 and had
a history of febrile convulsions (seizures) between the ages of 8
months and 2 years. Dr. Hyde opined that the seizures were a
typical indicator of abnormal brain function; and that a history of
head trauma may predispose a person to “some long-lasting
neurological effects from brain damage.” Nevertheless, Dr. Hyde
forward and make as many good statements as they could about the
defendant.” He also did not want to call the doctors as witnesses because there
was information in their reports—such as Jennings’s criminal history—that he
did not want the jury to know about, particularly because he was arguing for,
and received, the no significant criminal history statutory mitigator.
18 Specifically, Jennings reported to Dr. Hyde and Dr. Eisenstein that he was
hit in the head with a 2x4 piece of wood as a toddler; kicked in the head by a
pony at age 4 or 5; punched in the face as a teen; ran into a brick wall at age
16; engaged in a head-butting competition as a teen; was involved in multiple
fights and suffered blows to the head; and was involved in a motorcycle
accident (Jennings denied any head injury from motorcycle accident, but Dr.
Eisenstein opined that “it was impossible that he didn’t have a closed head
injury” from it).
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 20 of 38
20 Opinion of the Court 21-11591
opined that Jennings’s neurological examination was normal “for
the most part.” 19
Following testing, Dr. Eisenstein opined that Jennings was
“gifted” with learning disabilities that went untreated. 20 Dr.
Eisenstein also diagnosed Jennings with intermittent explosive
disorder, which is characterized by explosive aggressive responses
that are not proportionate to the provocation. Dr. Eisenstein
opined that the following statutory mitigating circumstances
applied to Jennings—(1) his capacity to appreciate the criminality
of his conduct or to conform his conduct to the law was impaired,
and (2) he was under the influence of an extreme mental or
emotional disturbance when he committed the murders.
Dr. Faye Sultan testified that her investigation revealed that
Jennings’s maternal grandfather was “overtly sexual” with his
daughters, and that Tawny (Jennings’s mother) was molested by
19 Dr. Hyde noted three “subtle neurological findings”—(1) Jennings’s pupils
were asymmetrical (one was larger than the other); (2) he had a “postural
tremor” in one hand; and (3) he had one unspecified “frontal release sign,” but
he admitted that these subtle findings can also be present “in normal
individuals.”
20 Dr. Eisenstein explained that some of Jennings’s scores were excellent,
while others were “indicative of a brain dysregulation” and a learning
disability. Dr. Eisenstein noted that although both Jennings and his mother
indicated that Jennings was a straight-A student, his school records—although
missing a number of years—revealed that was not true.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 21 of 38
21-11591 Opinion of the Court 21
her brother, George “Sonny” Jennings.21 Some of the people
Sultan interviewed witnessed Jennings sit on Sonny’s lap as a child,
and Jennings reported that Sonny paid him a quarter to sit on his
lap. Walter Croom, who married one of Jennings’s cousins, was
also a child molester, and he occasionally babysat Jennings.
However, Dr. Sultan confirmed that Jennings denied any sexual
abuse and there was no direct evidence indicating that any had
occurred, although she speculated it could have given the
environment that he grew up in. Dr. Sultan concluded that
Jennings grew up in extreme poverty and neglect and in an
environment that involved “the sexualization of children.” She
testified that children who grow up in that type of environment
“don’t develop normally neurologically” and are “quite impulsive,
sometimes aggressive, over sexualized themselves, often substance
abusers to the extreme.”
Based on her interviews with Jennings’s mother, Dr. Sultan
opined that Tawny was “quite mentally ill”—although she could
not offer any formal diagnosis—and Tawny had an “abnormal
attachment” to Jennings when he was a child. Dr. Sultan noted
that Tawny “behaved very oddly” toward Jennings, citing the fact
that Tawny breastfed him until he was five, and an unspecified
21 Tawny told Jennings at a very young age that she was a victim of sexual
abuse, and Dr. Sultan opined that such knowledge produces significant
emotional distress in children and “it certainly contributed” to “Jennings’[s]
state.” And Jennings stated that at one time, he believed his uncle Sonny might
be his biological father.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 22 of 38
22 Opinion of the Court 21-11591
person Sultan interviewed purportedly witnessed Tawny engage in
sex in the presence of Jennings. 22
Dr. Sultan’s interpretation of Jennings’s testing results “was
quite similar” to Dr. Masterson’s interpretation. Dr. Sultan
explained that Jennings was of above average intelligence, likely to
be a serious substance abuser, had difficulty controlling his anger,
was easily frustrated, extroverted, had a rigid personality, and was
able to have relationships with other persons, but they were not
likely to be long-lasting ones. Dr. Sultan also opined that Jennings
had intermittent explosive disorder. She further opined that
Jennings did not suffer from any mental illness, and that “he did not
meet the standards for [Florida’s] statutory mitigators.”
Nevertheless, she thought Jennings was “quite a damaged person”
who “operate[d] in the world . . . in a highly dysfunctional way.”
Finally, Jennings presented mitigation testimony from
family and friends. Jennings’s cousin, Patricia Scudder, testified
that, between the ages of 6 and 12, Jennings and Tawny lived in a
three-bedroom cabin-type home at the Buccaneer Apartments
(also known as the Buccaneer Motel). Scudder stayed with
Jennings and his mother for two-week periods on three different
22 Dr. Eisenstein similarly opined that Tawny was not a good mother, lacked
parenting skills, and was not an accurate historian of Jennings’s background
because she had been a victim of physical, sexual, and emotional abuse.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 23 of 38
21-11591 Opinion of the Court 23
occasions. 23 She described the condition of their apartment during
her first stay as “[v]ery, very messy” with clothes piled everywhere
and there were “[d]irty [k]otexes” around the apartment. But on
cross-examination, she clarified that the reason why she was
staying with them was because Jennings’s mother had just had
surgery, was immobile, and needed help. The second time Patricia
stayed with them, Jennings’s mother was again having health issues
and needed help. On this occasion, Jennings’s mother had a new
puppy, and there were puppy papers and dog poop on the floor,
and dirty dishes everywhere. Patricia stated that Tawny prepared
quick simple meals like toast, gravy, or hamburgers, and allowed
Jennings to eat a lot of junk food.
According to Patricia, Jennings regularly slept in the same
bed with his mother at 5 or 6 years’ old. On one occasion, Patricia
observed three men stay the night in Tawny’s home while Jennings
was home. The next morning after two of the men had left,
Patricia walked into the apartment, and Tawny and her boyfriend
were “cuddled up together” on the hide-a-bed in the living room,
unclothed—although not engaged in any sexual act—and Jennings
was lying on the floor watching tv. Nevertheless, despite her
testimony concerning the squalor of Jennings’s living conditions
and poor parenting skills of Tawny, Patricia described Jennings’s
23 Other than the three two-week periods that Patricia stayed with them, she
saw Jennings and his mother “[n]ot very often at all.” And she lost touch with
them after they moved in 1990, and she did not know anything about the case
until years after the trial.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 24 of 38
24 Opinion of the Court 21-11591
and his mother’s relationship as “very loving” and explained that
she had never “seen a mother and a son as close” as they were.
Patricia’s husband, Lloyd, testified that Sonny molested
Patricia, and Croom molested his and Patricia’s son, and that Sonny
and Croom had the opportunity to be around Jennings. Lloyd also
testified that he smoked marijuana with Tawny regularly, and that
she also took a lot of pain pills because of health issues. Lloyd
thought Tawny was a bad mother—describing her as selfish,
unemployed, and a poor housekeeper and cook. 24 Lloyd often
took Jennings fishing, taught him how to box, and did other things
with him, like a father figure. But Lloyd lost touch with Jennings
after Tawny moved from Oregon.
Next, Heather Johnson testified that she was “good friends”
with Jennings for a couple of years when they were 17 or 18 years’
old. She stated that Jennings often expressed unhappiness, conflict,
and resentment with his mother. At the time of Jennings’s trial,
Johnson no longer lived in Florida, but she was contacted via letter
by Jennings’s defense team, asking if she could give any “good
word” or character statement on behalf of Jennings and whether
she knew of anyone else who would be willing to testify on his
behalf. She wrote back stating that she was not sure that she could
be of much help because she and Jennings had lost contact and had
24 When asked how Tawny supported herself, Lloyd stated that she was on
welfare and speculated that she made money “[p]robably hooking.”
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 25 of 38
21-11591 Opinion of the Court 25
not spoken in years. 25 She did not hear back from Jennings’s
counsel, but she would have been willing to testify.
Lastly, Kevin McBride testified that he was friends with
Jennings when they were teenagers in Florida, and, at one point,
Jennings lived with him for a few months when Jennings’s mother
“was in between places.” He described Jennings’s mother as a
“very nice lady” who was “always friendly” but unstable
financially. He recalled that Jennings and his mother were more
like friends than mother and son. He stated that Jennings drank
and used marijuana on a daily basis, and he and Jennings used acid
and mushrooms on occasion.26 McBride confirmed that he met
with one of Jennings’s investigators at the time of Jennings’s trial,
but that he was not asked to testify.
25 Specifically, Johnson advised in her response that “[a]ll [she could] offer
[was] a brief summary of the Brandy Bain Jennings that [she] knew and loved,
and even that may not be a sterling character reference.” She went on to
describe that Jennings was her best friend, confidant, and protector—a big
brother type, who taught her things and made her feel safe. But he was also
“often foolish” and would do impulsive things without considering the
consequences. She stated that she believed he could have committed the
robbery because it was a way to act out the anger and frustration that he had
a difficult time expressing, but she did not believe him capable of murder. She
also advised that she could not think of anyone else who would be willing to
help Jennings.
26 Bruce Martin, half-brother to Kevin McBride, similarly testified at the
evidentiary hearing that Jennings drank heavily, used marijuana every day,
and used acid about once a week.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 26 of 38
26 Opinion of the Court 21-11591
ii. Trial Court Denies Jennings’s Postconviction Motion
Following the evidentiary hearing, the trial court denied
Jennings’s postconviction motion on the merits. Florida v.
Jennings, No. 1995-CF-02284,
2011 WL 11573988 (Fla. Cir. Ct. Jan.
31, 2011). The trial court concluded that counsel’s mitigation
investigation was not deficient because the record demonstrated
that counsel interviewed Jennings’s mother and various friends and
called witnesses during the penalty phase that he thought could
present positive information, which was “proper trial strategy.”
Id.
at *4–6. Finally, the trial court concluded that Jennings could not
show prejudice because, even if counsel had introduced all of the
information in question, there was no reasonable probability of a
different outcome.
Id. at *6. Jennings appealed to the Florida
Supreme Court.
iii. Florida Supreme Court’s Decision
The Florida Supreme Court determined that counsel made
a reasonable strategic decision to not present mitigation testimony
from Dr. Wald and Dr. Masterson during the penalty phase
“because it could open the door to other damaging testimony.”
Jennings v. State,
123 So. 3d 1101, 1114 (Fla. 2013) (Jennings II)
(quotation omitted). The court concluded that counsel was not
“deficient for choosing to pursue other mitigation evidence that he
determined was more likely to help Jennings at trial.”
Id. Finally,
the court held that Jennings failed to establish prejudice because
the trial court found as a nonstatutory mitigation that Jennings had
a deprived childhood, and the omitted information concerning
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 27 of 38
21-11591 Opinion of the Court 27
Jennings’s troubled childhood and emotional development did
“not rise to the level of unpresented mitigation previously held to
be prejudicial.”
Id. at 1117–18.
D. Federal § 2254 Habeas Proceeding
Following the denial of state postconviction relief, Jennings
filed a § 2254 federal habeas petition in the United States District
Court for the Middle District of Florida, raising several claims. As
relevant to this appeal, he combined his arguments that counsel
was ineffective for failing to conduct an adequate investigation into
mental health mitigation and his childhood background into a
single claim. Specifically, he argued that counsel was ineffective at
the penalty phase because (1) counsel’s mitigation investigation
was minimal and he failed to obtain medical or school records and
failed to provide such records to the experts; and (2) counsel made
no effort to truly investigate Jennings’s background and childhood,
which would have revealed a wealth of compelling mitigation. 27
The district court denied the petition, concluding that the
state court’s determination that counsel was not deficient was not
contrary to, or an unreasonable application of, Strickland v.
27 Jennings also took issue with the adequacy, sufficiency, and competency of
Dr. Wald’s and Dr. Masterson’s reports and Osteen’s reliance on those
allegedly deficient reports, but as his counsel acknowledged during oral
argument, that issue is beyond the scope of the COA in this case. See Murray
v. United States,
145 F.3d 1249, 1251 (11th Cir. 1998) (holding that “in an
appeal brought by an unsuccessful habeas petitioner, appellate review is
limited to the issues specified in the COA”).
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 28 of 38
28 Opinion of the Court 21-11591
Washington,
466 U.S. 668 (1984). Jennings v. Sec’y, Dep’t of Corr.,
No. 2:13-cv-751-FtM-38MRM,
2020 WL 7047706, *9–11 (M.D. Fla.
Dec. 1, 2020). Because the district court found that the
performance prong was not satisfied, it did not address the
prejudice prong.
Id. The district court denied Jennings a COA, and
he sought a COA from this Court.
Id. at *21. As noted previously,
we granted Jennings a COA on one issue: “Whether the district
court erred in denying Jennings’s claim that his trial counsel
rendered ineffective assistance in the penalty phase of his capital
trial by failing to conduct further investigation into Jennings’s
childhood and background.”
II. Standard of Review
We review the district court’s denial of a § 2254 habeas
petition de novo. Ward v. Hall,
592 F.3d 1144, 1155 (11th Cir.
2010).
The Antiterrorism and Effective Death Penalty Act of 1996
(“AEDPA”) establishes a “highly deferential standard for evaluating
state-court rulings, [and] demands that state-court decisions be
given the benefit of the doubt.” Cullen v. Pinholster,
563 U.S. 170,
181 (2011) (quoting Woodford v. Visciotti,
537 U.S. 19, 24 (2002)
(per curiam)). Thus, under AEDPA, a federal court’s review of a
final state habeas decision is greatly circumscribed, and a federal
habeas court cannot grant a state petitioner habeas relief on any
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 29 of 38
21-11591 Opinion of the Court 29
claim that was adjudicated on the merits in state court unless the
state court’s adjudication of the claim:
(1) resulted in a decision that was contrary to, or
involved an unreasonable application of, clearly
established Federal law, as determined by the
Supreme Court of the United States; or
(2) resulted in a decision that was based on an
unreasonable determination of the facts in light of the
evidence presented in the State court proceeding.
28 U.S.C. § 2254(d)(1)–(2).
“[C]learly established Federal law” means “the holdings, as
opposed to the dicta, of [the Supreme] Court’s decisions as of the
time of the relevant state-court decision.” Williams v. Taylor,
529
U.S. 362, 412 (2000). “[T]o be ‘contrary to’ clearly established
federal law, the state court must either (1) apply a rule that
contradicts the governing law set forth by Supreme Court case law,
or (2) reach a different result from the Supreme Court when faced
with materially indistinguishable facts.” Ward,
592 F.3d at 1155
(quotations omitted); see also Bell v. Cone,
535 U.S. 685, 694 (2002).
An “unreasonable application” of federal law occurs “if the
state court correctly identifies the governing legal principle from
[the Supreme Court’s] decisions but unreasonably applies it to the
facts of the particular case.” Bell,
535 U.S. at 694. “[A]n
unreasonable application of federal law is different from an
incorrect application of federal law.” Williams,
529 U.S. at 410
(emphasis omitted). “Indeed, ‘a federal habeas court may not issue
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 30 of 38
30 Opinion of the Court 21-11591
the writ simply because that court concludes in its independent
judgment that the relevant state-court decision applied clearly
established federal law erroneously or incorrectly.’” Renico v. Lett,
559 U.S. 766, 773 (2010) (quoting Williams,
529 U.S. at 411); see
also Shinn v. Kayer,
141 S. Ct. 517, 523 (2020) (“To meet [the
unreasonable application] standard, a prisoner must show far more
than that the state court’s decision was merely wrong or even clear
error.” (quotation omitted)). Rather, the state court’s application
of federal law “must be ‘objectively unreasonable,’” Renico,
559
U.S. at 773, meaning that “the state court’s decision is so obviously
wrong that its error lies beyond any possibility for fairminded
disagreement, Shinn, 141 S. Ct. at 523 (quotations omitted). “This
distinction creates a substantially higher threshold for obtaining
relief than de novo review.” Renico,
559 U.S. at 773 (quotation
omitted).
“[W]hen the last state court to decide a prisoner’s federal
claim explains its decision on the merits in a reasoned opinion . . .
a federal habeas court simply reviews the specific reasons given by
the state court and defers to those reasons if they are reasonable.”
Wilson v. Sellers,
138 S. Ct. 1188, 1192 (2018). However, we are
not limited by the particular justifications the state court provided
for its reasons, and we may consider additional rationales that
support the state court’s determination. Pye v. Warden, Ga. Diag.
Prison,
50 F.4th 1025, 1036 (11th Cir. 2022) (en banc). A state
court’s decision is reasonable “so long as ‘fairminded jurists could
disagree’ on the correctness of the state court’s decision.”
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 31 of 38
21-11591 Opinion of the Court 31
Harrington v. Richter,
562 U.S. 86, 101 (2011) (quoting Yarborough
v. Alvarado,
541 U.S. 652, 664 (2004)).
In addition, “a determination of a factual issue made by a
State court shall be presumed to be correct,” and the petitioner
bears “the burden of rebutting the presumption of correctness by
clear and convincing evidence.”
28 U.S.C. § 2254(e)(1). With these
principles in mind, we turn to the merits of Jennings’s appeal.
III. Discussion
Jennings argues that Osteen was constitutionally ineffective
by failing to adequately investigate and present mitigation
evidence related to his childhood and background, and in failing to
obtain and provide relevant background records to Dr. Wald and
Dr. Masterson.
To succeed on a claim of ineffective assistance of counsel in
violation of the Sixth Amendment, a petitioner must establish two
elements. Strickland,
466 U.S. at 687. “First, the defendant must
show that counsel’s performance was deficient.”
Id. Review of
counsel’s actions is “highly deferential” and “a court must indulge
a strong presumption that counsel’s conduct falls within the wide
range of reasonable professional assistance.”
Id. at 689.
“Second, the defendant must show that the deficient
performance prejudiced the defense.”
Id. at 687. Prejudice occurs
when there is a reasonable probability that, “but for counsel’s
unprofessional errors, the result of the proceeding would have
been different.”
Id. at 694. “When a defendant challenges a death
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 32 of 38
32 Opinion of the Court 21-11591
sentence . . . the question is whether there is a reasonable
probability that, absent the errors, the sentencer—including an
appellate court, to the extent it independently reweighs evidence—
would have concluded that the balance of aggravating and
mitigating circumstances did not warrant death.” 28
Id. at 695.
“The likelihood of a different result must be substantial, not just
conceivable.” Harrington,
562 U.S. at 112. In determining whether
there is a reasonable probability of a different result, a court must
“consider ‘the totality of the available mitigation evidence—both
that adduced at trial, and the evidence adduced in the habeas
proceeding’—and ‘reweig[h] it against the evidence in
aggravation.’” Porter v. McCollum,
558 U.S. 30, 41 (2009) (quoting
Williams,
529 U.S. at 397–98).
Because both prongs of the Strickland standard “must be
satisfied to show a Sixth Amendment violation, a court need not
address the performance prong if the petitioner cannot meet the
prejudice prong, and vice-versa.” Ward,
592 F.3d at 1163.
Furthermore, the Strickland standard is a general standard, which
means that “a state court has even more latitude to reasonably
determine that a defendant has not satisfied that standard.”
Knowles v. Mirzayance,
556 U.S. 111, 123 (2009); see also Renico,
28 Again, at the time of Jennings’s trial, only a majority 7-5 vote was necessary
to recommend death. Reynolds, 251 So. 3d at 827 (explaining that under
Florida’s old capital sentencing scheme, a jury “had various options for
recommendations, including life, 7–to–5 death, 8–to–4 death, 9–to–3 death,
10–to–2 death, 11–to–1 death, and unanimous death outcomes”).
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 33 of 38
21-11591 Opinion of the Court 33
559 U.S. at 776 (“Because AEDPA authorizes federal courts to grant
relief only when state courts act unreasonably, it follows that ‘[t]he
more general the rule’ at issue—and thus the greater the potential
for reasoned disagreement among fair-minded judges—‘the more
leeway [state] courts have in reaching outcomes in case-by-case
determinations.’” (quoting Yarborough,
541 U.S. at 664)).
Here, we need not address Jennings’s arguments related to
the performance prong because the Florida Supreme Court’s
determination that Jennings failed to establish prejudice was not
contrary to, or an unreasonable application of, Strickland or based
on an unreasonable determination of the facts. The mitigation
evidence offered in Jennings’s postconviction proceedings
primarily related to non-statutory mitigation. Specifically, in
addition to Jennings’s positive character traits and relationships
that the jury and judge originally heard during the penalty phase,
had the evidence submitted at the postconviction proceeding been
presented at the penalty phase, the jury and the sentencing judge
would also have learned of Jennings’s chaotic childhood; his
mother’s poor parenting skills; his family’s history of sexual
abuse; 29 Jennings’s drug and alcohol abuse; his history of head
29 Jennings argues that the Florida Supreme Court unreasonably discounted
the evidence of sexual abuse in his family and the effect that such an
environment would have had on Jennings’s emotional and mental
development in contravention of the Supreme Court’s decision in Porter.
Contrary to Jennings’s argument, the Florida Supreme Court did not discount
the evidence of sexual abuse to “irrelevance” but instead determined that it
was of minimal value because evidence of sexual abuse of Jennings’s family
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 34 of 38
34 Opinion of the Court 21-11591
injuries and febrile seizures; that his neurological testing was
normal despite repeated head injuries; that he did not have any
mental illness; that he had intermittent explosive disorder and that
two experts believed he had sociopathic personality traits; that
Jennings had above-average intelligence; and that he had a history
of criminal acts, some of which were violent.
Given the facts of this case, it was not unreasonable for the
state court to conclude that Jennings was not prejudiced by
counsel’s failure to present the mitigation evidence in question
during the penalty phase. As an initial matter, there is a significant
probability that much of the omitted mitigation evidence when
combined with that adduced at trial, would have undermined
some of the mitigating factors that the trial court found—namely,
that (1) Jennings had no significant prior criminal history
(Jennings’s only statutory mitigating factor), (2) he had a close,
loving relationship with his mother, and (3) he had “positive
personality traits enabling the formation of strong, caring
relationships with peers.” And we have held that it is not an
members “might have been mitigating in establishing [his] troubled childhood
and emotional development,” but the trial court already found as a non-
statutory mitigating factor that he had a deprived childhood. Jennings II,
123
So. 3d at 1118. It was not contrary to, or an unreasonable application of,
clearly established federal law for the Florida Supreme Court to determine
that the evidence of familial sexual abuse was of minimal value given that
Jennings expressly denied any personal history of sexual abuse, and there was
no other evidence indicating that Jennings himself suffered any sexual abuse
from any family members.
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 35 of 38
21-11591 Opinion of the Court 35
unreasonable application of Strickland to conclude that there is no
prejudice when much of the mitigation evidence would have
constituted a double-edged sword. See Gavin v. Comm’r, Ala.
Dep’t of Corr.,
40 F.4th 1247, 1269 (11th Cir. 2022) (holding that
mitigation evidence “could have been a double-edged sword,” and,
therefore, the state court reasonably applied Strickland when it
concluded that petitioner could not establish prejudice); Ponticelli
v. Sec’y, Fla. Dep’t of Corr.,
690 F.3d 1271, 1296 (11th Cir. 2012)
(“[B]oth the Supreme Court and this Court have consistently
rejected [the] prejudice argument [ ] where mitigation evidence
was a two-edged sword or would have opened the door to
damaging evidence.” (second and third alterations in original)
(quotations omitted)).
Furthermore, there were significant aggravating factors
present in this case—(1) the murders were committed while
Jennings was engaged in or was an accomplice in the commission
of a robbery; (2) the murders were committed for the purpose of
avoiding or preventing a lawful arrest or to effectuate an escape
from custody; and (3) the crimes were committed in a cold,
calculated, premeditated manner. Notably, the cold, calculated,
and premeditated factor is one of “the weightiest aggravating
factors in Florida’s capital sentencing scheme.” Carr v. State,
156
So. 3d 1052, 1071 (Fla. 2015) (quotations omitted). And as the state
postconviction court noted, the nature of, and circumstances
surrounding, the three murders in this case were particularly
heinous. “We’ve repeatedly held that even extensive mitigating
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 36 of 38
36 Opinion of the Court 21-11591
evidence wouldn’t have been reasonably likely to change the
outcome of sentencing in light of a particularly heinous crime and
significant aggravating factors.” Pye, 50 F.4th at 1049 (collecting
cases); see also Puiatti v. Sec’y, Fla. Dep’t of Corr.,
732 F.3d 1255,
1287–88 (11th Cir. 2013) (holding that petitioner could not show
prejudice based on mitigation evidence of depraved, impoverished,
and abusive childhood where one of the aggravating factors was
the cold, calculated, and premeditated aggravator). Thus, in light
of the facts of this case, we cannot say that the Florida Supreme
Court’s determination that Jennings did not suffer prejudice was so
obviously wrong as to be beyond any possibility for fairminded
disagreement, which is “the only question that matters” under
§ 2254(d). Shinn, 141 S. Ct. at 526; see also Jones v. Sec’y, Fla. Dep’t
of Corr.,
834 F.3d 1299, 1312–17 (11th Cir. 2016) (holding that state
court’s determination that the petitioner failed to demonstrate
prejudice was reasonable where the mitigating evidence was of
limited value and there were significant aggravating factors).
To the extent that Jennings argues that his case is analogous
to Porter or Sears v. Upton,
561 U.S. 945 (2010), and that those
cases compel a finding of prejudice in this case, his argument is
unpersuasive. The mitigating evidence in Porter was significantly
more compelling than that presented in Jennings’s case. For
instance, in Porter, the jury never heard that (1) he suffered from
brain damage that could result in “impulsive, violent behavior”;
(2) that he had “heroic military service in two of the most critical—
and horrific—battles of the Korean War”; (3) he suffered from
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 37 of 38
21-11591 Opinion of the Court 37
mental health issues following the war; (4) he had an extensive
history of childhood physical abuse by his father; and (5) that
Porter was in special education classes and left school at the age of
12 or 13.
558 U.S. at 33–37, 41. More importantly, in Porter, the
Supreme Court reasoned that, had the jury heard this extensive
mitigation, there was a reasonable probability that the jury would
have struck a different balance given that there appeared to be only
one aggravating factor that tipped the scales in favor of a death
sentence.
Id. at 41–42. In contrast, although Jennings’s mitigation
evidence included details about a deprived and impoverished
childhood and that he had a history of head trauma, there was no
evidence of brain dysfunction, mental illness—indeed Jennings’s
experts opined that he was very intelligent with no mental
disorders or brain dysfunction—or physical or sexual abuse, and
Jennings’s death sentence was supported by three significant
aggravating factors. Given the significant differences between
Porter and the case at hand, Porter cannot compel a finding of
prejudice in this case.
Similarly, the mitigation evidence in Sears was far stronger
than that in Jennings’s case. The mitigation evidence in Sears
included that (1) Sears “suffer[ed] from substantial cognitive
impairment” and he was “among the most impaired individuals in
the population in terms of ability to suppress competing impulses
and conform behavior”; (2) he had a history of head trauma and
“significant frontal lobe abnormalities”; (3) he grew up in a volatile,
physically abusive home; and (4) he suffered sexual abuse from a
USCA11 Case: 21-11591 Document: 30-1 Date Filed: 12/13/2022 Page: 38 of 38
38 Opinion of the Court 21-11591
family member.
561 U.S. at 948–50. Furthermore—and this is a
crucial difference—Sears was not subject to AEDPA’s deferential
review standard because the Sears appeal was not from a federal
petition for a writ of habeas corpus; instead, Sears had appealed
from the state court’s decision directly to the United States
Supreme Court.
Id. at 946. Moreover, Sears did not involve a
finding of prejudice. Rather, the Supreme Court determined that
the state court failed to apply the proper prejudice inquiry, and it
remanded the case for the state court to conduct “[a] proper
analysis of prejudice” in the first instance.
Id. at 956 (“It is for the
state court—and not for either this Court or even [the dissenting
Justice]—to undertake [the prejudice inquiry] in the first
instance.”). Thus, Sears cannot compel a finding of prejudice in
Jennings’s case.
Accordingly, we affirm the district court’s denial of
Jennings’s habeas petition.
AFFIRMED.