United States v. Pineda-Buenaventura

In the
United States Court of Appeals
For the Seventh Circuit
Nos. 09-1500, 09-1525, 09-1875 & 09-2431
U NITED S TATES OF A MERICA,
Plaintiff-Appellee,
v.
T EODULO P INEDA-B UENAVENTURA ,
O TONIEL M ENDOZA, G ERARDO P INEDA-SORIA, and
A RTURO P INEDA-L OPEZ,
Defendants-Appellants.
Appeals from the United States District Court
for the Western District of Wisconsin.
No. 08-CR-105—Barbara B. Crabb, Judge.
A RGUED M ARCH 31, 2010—D ECIDED S EPTEMBER 15, 2010
Before M ANION and W ILLIAMS, Circuit Judges, and
D ARRAH, District Judge.Œ
W ILLIAMS, Circuit Judge. This is a consolidated appeal
of four defendants involved in a large cocaine distribu-
Œ
The Honorable John W. Darrah, United States District Court
for the Northern District of Illinois, Eastern Division, sitting
by designation.
2 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
tion conspiracy that operated in Jefferson County, Wis-
consin. Following an investigation involving wiretap
surveillance, controlled purchases, and confidential in-
formants, sixteen individuals were charged in two
separate indictments for conduct related to the conspir-
acy. The four defendants involved here—Teodulo Pineda-
Buenaventura, Otoniel Mendoza, Gerardo Pineda-Soria,
and Arturo Pineda-Lopez—each pled guilty to pos-
sessing or conspiring to possess with intent to distribute
cocaine. Each now appeals. Teodulo Pineda-Buenaventura
challenges his sentence, arguing that the drug amount
calculation in his presentence investigation report was
insufficient to support the statutory mandatory mini-
mum sentence he received. Otoniel Mendoza challenges
the validity of his guilty plea, arguing that his plea col-
loquy did not satisfy the requirements of Federal
Rule of Criminal Procedure 11. Gerardo Pineda-Soria
appeals the denial of his motion to suppress drugs
found in his apartment and statements he made there-
after, arguing that the search violated the Fourth Amend-
ment. And Arturo Pineda-Lopez’s attorney has filed an
Anders brief, seeking to withdraw on the basis that there
are no non-frivolous arguments to be made by Pineda-
Lopez on appeal.
For the reasons explained below, we vacate Pineda-
Buenaventura’s sentence and remand for resentencing
because the district court’s drug quantity findings
did not support the sentence he received. We also
vacate Mendoza’s conviction because his plea colloquy
did not satisfy the requirements of Rule 11, and so we
remand for further proceedings. Furthermore, we affirm
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 3
the district court’s denial of Pineda-Soria’s motion to
suppress because he and his co-tenants gave valid
consent to search his apartment. Finally, we grant
Pineda-Lopez’s counsel permission to withdraw because
a challenge to the reasonableness of his sentence would
be frivolous.
I. TEODULO PINEDA-BUENAVENTURA—DRUG
AMOUNT FINDING
Teodulo Pineda-Buenaventura was a “runner” in the
drug conspiracy who delivered cocaine at the direc-
tion of his cousin, Efrain Pineda-Buenaventura, one of
the co-leaders of the conspiracy.1 On June 19, 2008, after
wiretap surveillance, police executed a search warrant
at his home and recovered cocaine, a digital scale, a
firearm, and $16,000 in cash. He was arrested, admitted
to his involvement in the conspiracy, and on Decem-
ber 10, 2008, pled guilty pursuant to a written plea agree-
ment to a single count of conspiracy to possess with
intent to distribute at least 500 grams of cocaine. The
plea agreement provided that he was subject to a
60-month mandatory minimum term of imprisonment
pursuant to 21 U.S.C. § 841(b)(1)(B), but offered no
details as to the specific amount of drugs to which he
was admitting responsibility. At the plea hearing, the
1
“Pineda-Buenaventura” refers to defendant-appellant Teodulo
Pineda-Buenaventura. When we refer to Efrain Pineda-
Buenaventura, we do so using his full name so as to avoid
confusion.
4 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
government acknowledged that while the count to
which Pineda-Buenaventura was pleading was based
on an amount of at least 500 grams, if the presentence
investigation resulted in a finding that he was re-
sponsible for less, he would only be held accountable
for that lower amount.
Pineda-Buenaventura’s presentence investigation re-
port (“PSR”) stated that 105 grams of cocaine were re-
covered from his home during the execution of the
search warrant and that wiretap surveillance showed
he had made deliveries totaling approximately 300
grams of cocaine. The PSR also found that Pineda-
Buenaventura made 22 additional deliveries in which
the drug quantities “could not be determined.” Based on
these findings, the PSR stated that “[t]he probation
office believes that Teodulo’s relevant conduct involves
at least 400 grams to 500 grams of cocaine, resulting in
a base offense level of 24. This is a conservative estimate.”
At Pineda-Buenaventura’s sentencing hearing, the
district judge imposed the statutory minimum sentence
of 60 months based on responsibility for 500 or more
grams of cocaine. The district court appeared to agree
with the findings in the PSR—including, presumably,
its estimate that Pineda-Buenaventura was responsible
for “at least” 400 to 500 grams of cocaine—but then
stated “[y]our relevant conduct involves at least 400
grams but less than 500 grams of cocaine.” (emphasis
added). Apparently, the district judge believed that
Pineda-Buenaventura was responsible for at least 500
grams (given that she sentenced him to a mandatory
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 5
minimum based on that amount), but then made an
express finding that he was responsible for less than
that amount.
Pineda-Buenaventura contends that his PSR does not
establish that he was responsible for at least 500 grams of
cocaine in the conspiracy, the amount necessary for the
charge to which he pled. Because he forfeited this argu-
ment by failing to challenge the PSR’s amount deter-
minations below (he admits this), the sentence is re-
viewed for plain error.2 United States v. Jacques, 345 F.3d
960, 962 (7th Cir. 2003). Under this standard of review,
we affirm a sentence unless, after considering all the
evidence, we have a “definite and firm conviction that
a mistake has been committed.” United States v. Haynes,
582 F.3d 686, 709 (7th Cir. 2009) (quotation omitted).
We find that while the PSR may support a finding that
Pineda-Buenaventura was responsible for at least 500
grams under the evidentiary standards applicable at
sentencing, remand is necessary because the sentencing
judge made a finding on the record that Pineda-
Buenaventura was responsible for less than that amount.
2
The government argues that Pineda-Buenaventura waived,
not merely forfeited, appeal on this issue. But waiver is an
intentional, strategic decision not to raise a challenge, whereas
an argument is forfeited when the issue is not raised neg-
ligently or accidentally. See United States v. Cooper, 243 F.3d
411, 416 (7th Cir. 2001). We can discern no tactical reason
behind Pineda-Buenaventura’s failure to raise this argument.
See United States v. Jaimes-Jaimes, 406 F.3d 845, 848 (7th Cir.
2005) (“Waiver principles should be construed liberally in
favor of the defendant.”).
6 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
Evidentiary standards at sentencing are not as
stringent as those at trial. United States v. Taylor, 72
F.3d 533, 543 (7th Cir. 1995). A district court can deter-
mine drug quantities attributable to a defendant based
only on a preponderance of the evidence, United States
v. Salinas, 62 F.3d 855, 859 (7th Cir. 1995), and can rely
on the findings set forth in a PSR so long as the infor-
mation has “sufficient indicia of reliability to support
its probable accuracy.” U.S.S.G. § 6A1.3(a). That said, we
have encouraged courts to “make conservative estimates
[of drug amounts], especially when presented with gen-
eralized testimony, as a way to . . . approximate drug
quantities.” United States v. Henderson, 58 F.3d 1145,
1152 (7th Cir. 1995). Here, while the facts set forth
in Pineda-Buenaventura’s PSR would arguably support
a finding that he was responsible for over 500 grams of
cocaine under the standard we just described, the sen-
tencing judge’s express statement that his relevant
conduct involved “less than 500 grams” forecloses any
such interpretation and compels remand.
“A sentencing based on an incorrect Guidelines range
constitutes plain error and warrants a remand for
resentencing, unless we have reason to believe that the
error in no way affected the district court’s selection of
a particular sentence.” United States v. Farmer, 543 F.3d
363, 375 (7th Cir. 2008). Here, relevant conduct in-
volving an amount between 400 and 499 grams—the
amount expressly referenced by the district judge—
would have generated an advisory Guideline range of
46-57 months, not the 60-month minimum set forth
in § 841(b)(1).
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 7
Remand will provide the district court with an oppor-
tunity to clarify its findings regarding the drug amount
attributable to Pineda-Buenaventura and to impose
an appropriate sentence for that amount. See, e.g., United
States v. Salem, 597 F.3d 877, 887-88 (7th Cir. 2010) (re-
manding for resentencing when findings were insuf-
ficient to support sentence imposed). It is possible that
the sentencing judge merely misspoke when making
the finding that Pineda-Buenaventura’s relevant conduct
involved “less than 500 grams,” but there is no way to
be sure of this, especially when the PSR on its own
terms does not unequivocally establish that Pineda-
Buenaventura was responsible for at least 500 grams
of drugs. See id. at 888 (if court relies on PSR to make a
finding as to certain conduct, the PSR must actually
define that conduct); see also Farmer, 543 F.3d at 375 (“We
have no reason to believe that the district court would
not have selected an even lower sentence if given the
opportunity to do so, thus, we must remand.”).
II. OTONIEL MENDOZA—RULE 11 PLEA COLLO-
QUY
Otoniel Mendoza was another “runner” that delivered
cocaine in the conspiracy. A search warrant executed
at Mendoza’s home yielded 339 grams of cocaine and
9 grams of methamphetamine. Wiretap surveillance
revealed that he had delivered an additional 283 grams
of cocaine, and made 21 additional deliveries for which
the amount could not be determined. On December 12,
2008, Mendoza pled guilty to a single count of conspiracy
8 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
to possess at least 500 grams of cocaine with intent to
distribute, pursuant to a written plea agreement. The
agreement stated that he was subject to a 60-month man-
datory minimum term of imprisonment per 21 U.S.C.
§ 846, but did not discuss any relevant conduct to which
he was pleading.
Mendoza makes two arguments on appeal: (1) that
his plea colloquy did not satisfy Rule 11’s requirement
that his plea be knowing and voluntary, and (2) that the
facts upon which his mandatory minimum sentence
was based must be found by a jury. We address each in
turn.
A. Mendoza’s Plea Colloquy Did Not Satisfy Rule 11
Mendoza claims that his guilty plea to conspiring to
distribute cocaine fell short of Rule 11’s requirement
that it be knowing and voluntary. He argues that the
district court failed to ensure that he understood the
nature of the conspiracy charge to which he was
pleading, that he never clearly pled guilty to specific acts
in furtherance of that conspiracy, and that he was never
clearly told he was pleading to an offense with a five-
year mandatory minimum sentence.
A careful review of Mendoza’s colloquy with the court
at his plea hearing—relevant portions of which we
quote below—demonstrates that Mendoza was indeed
confused with the concept of the conspiracy to which
he was pleading, and was equivocal in many of his an-
swers to the court regarding his conduct. We cannot
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 9
say with confidence that Mendoza ever truly under-
stood the nature of the conspiracy to which he was ad-
mitting involvement, nor can we determine exactly
what acts Mendoza believed he was admitting to. We
conclude that the plea colloquy fell short of Rule
11(b)(1)(G)’s requirement that Mendoza understand
the nature of the charge to which he pled guilty.
1. The Plea Colloquy
Problems began early in Mendoza’s exchange with
the court, which took place through a translator due
to Mendoza’s limited English. Asked by the district
judge whether he understood that the government was
charging him with agreeing with others to distribute
drugs, he answered “Yes. But the one thing about us
coming to an agreement isn’t so”—displaying a lack of
agreement with a critical element of a conspiracy.
Noticing Mendoza’s apparent confusion, the district
court attempted to clarify Mendoza’s understanding of
the conspiracy, and the following exchange occurred:
THE COURT: When you talk about a conspiracy,
it’s not saying that you all sat around a table and
agreed on each and every part of the conspiracy.
The Government has to show that you did agree
to something that carried out the conspiracy. The
Government says that this conspiracy involved
cocaine and it involved at least 500 grams of co-
caine. That doesn’t—the Government isn’t saying
that you yourself were responsible for dis-
tributing 500 grams, but it does say that the con-
10 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
spiracy, all of the people involved conspired to
distribute 500 grams or more.
MENDOZA: I just have one question.
THE COURT: Yes.
MENDOZA: Could you tell me more or less
how many people are in the conspiracy?
THE COURT: According to the Indictment, there’s
seven that are named. That includes you, but
then the Indictment also talks about others who
may or may not be known to the grand jury.
MENDOZA: Well, the thing is that I wasn’t in
contact with those people. I don’t know those
people, and I can’t name them here in the papers.
The district judge again attempted to clarify by explaining
that Mendoza need not have specifically reached agree-
ment with each member of the conspiracy, to which
he vaguely replied “[w]ell, maybe I’m pleading guilty
because I did sell a few times.” When the court at-
tempted to again determine whether Mendoza under-
stood the government’s allegations as to what he had
done, Mendoza’s answer was still equivocal: “Yes, I do
understand, but I need to see a little bit more. I don’t
know how much the Government may have.”
Later in the hearing, the government proffered some of
the evidence it would have introduced had Mendoza
chosen to go to trial. The government referred to inter-
cepted telephone calls between Mendoza and Efrain
Pineda-Buenaventura in which Mendoza was directed to
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 11
deliver cocaine; Mendoza’s own admission at the time
of his arrest that he had delivered cocaine; and evidence
that had been seized at Mendoza’s apartment, including
200 grams of cocaine, a digital scale, and packaging
materials. Asked whether he disputed any of the evi-
dence the government said it could prove, Mendoza
said that he did not.
Mendoza was then asked to describe in his own
words what he had done in connection with the con-
spiracy, however, and this is where things again got
problematic. Mendoza began by vaguely describing
his relationship with Efrain Pineda-Buenaventura, but
did not initially describe any activity involving the
delivery of cocaine. The court sought to focus matters
and the following exchange ensued:
THE COURT: Did you—did you deliver drugs
to [Efrain] Pineda-Buenaventura? Did you pick up
drugs from him?
MENDOZA: No.
THE COURT: Did you do any of the things that
Mr. Connell [government lawyer] talked about?
MENDOZA: I don’t remember too well what it
was that he said, but—
The government lawyer then offered to assist by re-
iterating some of the government’s proof against
Mendoza, which the court invited him to do. The gov-
ernment lawyer again referred to intercepted telephone
calls in which Efrain Pineda-Buenaventura instructed
12 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
Mendoza to deliver drugs to various persons, and also
again referred to Mendoza’s own statement at his arrest
that he had in fact delivered drugs at Efrain Pineda-
Buenaventura’s direction. When the court turned back
to Mendoza and sought to confirm his understanding of
this, this exchange occurred, which we quote at length:
THE COURT: Did [Efrain] Pineda-Buenaventura
call you and ask you or tell you to deliver drugs?
MENDOZA: He told me to go and deliver some
CDs that some people had lent to him.
THE COURT: All right. I’m not going any farther
with this. Mr. Mendoza, if you don’t agree that you
did any of the things that Mr. Connell says you
did, we’ll continue this trial—this for trial.
MENDOZA: Well, there is a part that I am guilty of
there, but the thing is though in part they are
pinning a lot of stuff on me and I don’t believe
I did all of that.
THE COURT: All right. I’ll start—I’ll give you one
last chance and then I have other matters that
I need to take care of, Mr. Mendoza, and I’m not
interested in spending more time with you if
you’re not willing to take any responsibility. We’ll
just go to trial. We’ll have a jury decide what
happened in this case. I’ll ask you once again, did
you deliver any cocaine at the request of any of
the people that you conspired with? Mr. Delyea
[defense counsel].
DEFENSE COUNSEL: Actually the point I made
is did you ever just do it one time. Apparently
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 13
there were times when they delivered CDs and
DVDs.
THE COURT: I’m not interested in that.
DEFENSE COUNSEL: I understand.
THE COURT: I just want to know whether he
ever delivered cocaine.
DEFENSE COUNSEL: If there was ever one occa-
sion.
THE COURT: Ever. Any occasion on which he
delivered cocaine with any of the people named
in the Indictment or others.
MENDOZA: Yes, there was one time. But not
specifically in the calls, but one time, yes.
THE COURT: And who called you and asked you
to deliver cocaine?
MENDOZA: Well, it wasn’t directly—it wasn’t
directly somebody calling me and saying well,
let’s deliver cocaine to so-and-so. I think it was
cocaine—well, I never had this, but I think it
was cocaine.
THE COURT: But who asked you to deliver it?
MENDOZA: Well they called me and had
me—Efrain called me to have me take that over to
someone who I guess had ordered it from him.
I don’t know how they ordered the stuff from him.
THE COURT: You don’t need to know that. Who
called you? [Efrain] Pineda-Buenaventura?
14 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
MENDOZA: Yes, him.
THE COURT: All right. Then on the basis of this
extended discussion with counsel and with
Mr. Mendoza and upon the basis of the entire
record in the case, I find and conclude,
Mr. Mendoza, that you have entered a plea of
guilty knowingly, understandingly, and volun-
tarily . . . .
2. Analysis
Mendoza claims that his plea colloquy did not comply
with Rule 11 because he never understood the nature of
the charge against him. Because Mendoza never sought
to withdraw his plea in the district court, our review is
for plain error. United States v. Vonn, 535 U.S. 55, 63
(2002); United States v. Burnside, 588 F.3d 511, 520
(7th Cir. 2009). We review Mendoza’s claim of a
Rule 11 violation to determine whether (1) an error has
occurred; (2) it was plain; (3) it affected Mendoza’s sub-
stantial rights; and (4) it seriously affected the fair-
ness, integrity, or public reputation of the judicial pro-
ceedings. See Burnside, 588 F.3d at 520.
Rule 11 requires that “before the court accepts a plea
of guilty or nolo contendere . . . the court must address
the defendant personally in open court . . . [and] inform
the defendant of, and determine that the defendant
understands . . . the nature of each charge to which
the defendant is pleading.” Fed. R. Crim. P. 11(b)(1)(G). It
requires that a district court “ensure that [the defendant]
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 15
understands the law of his crime in relation to the facts
of his case.” Vonn, 535 U.S. at 62. Unless a defendant
“fully comprehends the elements of the crime to which
he is confessing, his plea cannot be said to have been
knowingly and voluntarily entered.” United States v.
Fernandez, 205 F.3d 1020, 1025 (7th Cir. 2000) (quota-
tion and citation omitted). To determine whether a de-
fendant in fact understands the nature of a charge, we
take a totality-of-the-circumstances approach and con-
sider (1) the complexity of the charge; (2) the de-
fendant’s intelligence, age, and education; (3) whether
the defendant was represented by counsel; (4) the
district judge’s inquiry during the plea hearing and the
defendant’s own statements; and (5) the evidence
proffered by the government. Id. (citing United States
v. LeDonne, 21 F.3d 1418, 1423 (7th Cir. 1994)).
Our assessment of these factors in Fernandez is instruc-
tive here. In Fernandez, a native Spanish-speaking defen-
dant with a fifth grade education and limited English
pled guilty to conspiring to distribute marijuana. 205
F.3d at 1022. At his plea hearing, Fernandez, like
Mendoza here, demonstrated confusion both with the
concept of the conspiracy and the specific acts to which
he was pleading guilty. Id. at 1025-27. In his exchanges
with the court, Fernandez gave ambiguous, partial, and
even contradictory answers, and at times appeared con-
fused. Id. For example, when asked by the court whether
he had done the things set forth in the government’s
proffer, Fernandez gave inconsistent and unclear
answers, varying from “Yes, your Honor, I did,” to “[n]ot
16 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
everything. I thought I was pleading guilty partially,” to
“[n]ot all of the acts, partially.” Id. at 1026-27.
On appeal, Fernandez argued his plea was not
voluntary, and we agreed, finding the guilty plea
to have been “enveloped in confusion and misunder-
standing.” Id. at 1026. Reviewing the record, we found
that Fernandez exhibited confusion over the nature of
the conspiracy, and that “like most lay people, Fernandez
would not understand the term ‘conspiracy’ without
some further explanation.” Id. at 1026. We also found
that there was general confusion regarding “precisely
what acts Fernandez admitted.” Id. at 1027. We con-
cluded that “Fernandez’ accounts of what acts he ad-
mitted and those he denied were very murky. Based
on this record, it is impossible to ascertain precisely
what acts Fernandez admits and which he denies.” Id.
Evaluating the totality of the circumstances, we held
that “we cannot conclude that Fernandez was fully
aware of the nature of the crime to which he pleaded
guilty” and remanded the case to the district court for
a new plea. Id. at 1026, 1030.
Reviewing the record here (especially the portions
quoted above) in light of Fernandez and the relevant
factors, we cannot say with confidence that Mendoza
ever truly understood the nature of the conspiracy to
which he was pleading. Mendoza demonstrated confu-
sion with the concept of the conspiracy, and that confu-
sion was never fully resolved by the court. Nor can we
clearly determine exactly what acts Mendoza admitted.
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 17
The first two factors in our totality-of-the-circumstances
approach—complexity of the charge and defendant’s
age and education—mitigate against a finding that
Mendoza understood exactly what he was pleading to.
Conspiracy is not a concept immediately under-
standable to a layperson. See United States v. Blalock, 321
F.3d 686, 689 (7th Cir. 2003) (“[C]onspiracy is generally
considered a rather complicated offense.”); see also United
States v. Wetterlin, 583 F.2d 346, 350 (7th Cir. 1978) (charge
of conspiracy “is not a self-explanatory legal term”). The
relative complexity of a conspiracy charge, coupled
with Mendoza’s sixth-grade education level and lim-
ited English, favor a finding that Mendoza did not com-
prehend the charge to which he was pleading. See
Fernandez, 205 F.3d at 1026.
The fact that Mendoza was represented by counsel—
the third factor in our inquiry—did not alleviate the
problems we perceive here. At certain points during the
plea hearing, Mendoza’s lawyer did attempt to clarify
matters for his client and the court, but those attempts
are not a substitute for Mendoza himself actually indi-
cating an understanding of the charge to which he was
pleading. At certain points during the hearing, counsel’s
presence almost seems to have complicated matters—
at times when meaningful follow-up questions might
have confirmed Mendoza’s understanding, counsel
instead stepped in and offered comments that took the
court in another direction. Moreover, Mendoza himself
indicated at the beginning of the hearing that there had
been some communication problems with his lawyer.
Asked by the court whether counsel had answered all of
18 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
his questions, Mendoza answered, “Well, I’m not really
clear on some of them, but others, yes.” Mendoza in-
dicated that he was not sure if his lawyer had understood
him in their conversations, stating that “[h]e doesn’t
speak my Spanish.” And counsel himself informed the
court at the close of the plea hearing that he and
Mendoza had had “some difficulty communicating.”
The fourth factor—the district judge’s inquiry during
the plea hearing and the defendant’s own statements—
is the most troubling. A careful review of the plea
colloquy demonstrates that Mendoza never seemed
to have a real grasp of what the conspiracy was. The
court made attempts to clarify and explain the con-
spiracy to Mendoza, but the record shows that he at
best indicated only partial understanding, and at times
made statements that entirely undercut it—such as “the
one thing about us coming to an agreement isn’t so”
and “I wasn’t in contact with those people.” Further
attempts were made to clarify matters, to which
Mendoza only stated that he would “need to see a little
bit more” in order to understand, because he didn’t
“know how much the Government may have.”
And when it came time for Mendoza to explain in
his own words what he did, his accounts were
noncommital, vague, and evasive. Mendoza repeatedly
hedged in his answers and descriptions of his conduct
to the court, prompting numerous (fruitless) clarifying
questions from the court. At one point, he even dis-
cussed delivering compact discs for Efrain Pineda-
Buenaventura instead of drugs. Eventually, after signifi-
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 19
cant back-and-forth with the court —during which time
the district judge told Mendoza that he had “one last
chance,” that she had “other matters . . . to take care of,”
and that “I’m not interested in spending more time with
you if you’re not willing to take any responsibility”—
Mendoza finally stated that Efrain Pineda-Buenaventura
had on one occasion instructed him to deliver drugs to
someone. This lone statement is eclipsed in context by
the significant confusion that preceded it. At any point
during the colloquy, the district court could have taken
a brief recess in order to allow counsel to talk with his
client confidentially, address Mendoza’s apparent con-
fusion, and determine if he did indeed wish to proceed
with a plea. Such a conference might have helped to
avoid the problems that occurred here. But based on this
record, we cannot be confident that Mendoza under-
stood the nature of the crime to which he was pleading
guilty, or exactly which acts he was admitting having
committed. See Fernandez, 205 F.3d at 1027. The fourth
factor in our totality-of-the-circumstances inquiry favors
Mendoza.
The fifth factor in our inquiry examines the govern-
ment’s proffered evidence. Examining this factor in
Fernandez, we found that “while there was nothing
wrong with the AUSA’s factual proffer on its face, the
surrounding chaos at this change of plea hearing sig-
nificantly negated any confidence in Fernandez’ under-
standing of and admission to those facts.” Id. The same
could be said here. The government’s explanation of its
evidence against Mendoza was sufficient, but Mendoza’s
20 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
various reactions to it undermine our confidence that
he understood the acts to which he was admitting. While
Mendoza initially said that what the government had
proffered was “fair,” he then later stated that he did not
remember what the government’s evidence was. Even
when the proffer was reiterated, he showed further
confusion and was evasive. Just as in Fernandez, where
we were concerned with a defendant who admitted to,
in his words, “[n]ot all of the acts, partially,” here Mendoza
was similarly noncommital, saying “there is a part that
I am guilty of there, but the thing is . . . I don’t believe
I did all of that.” See id. (“Because we cannot glean a
clear understanding of Fernandez’ participation in the
crime charged, it is impossible to determine whether
Fernandez himself understood the nature of the crime
to which he was pleading guilty.”). Mendoza’s tentative,
qualified responses to the government’s proffered evi-
dence undermine our confidence that he really did under-
stand exactly what to which he was pleading guilty. See id.
We find that the Rule 11 errors that occurred during the
plea colloquy in this case were plain and affected
Mendoza’s substantial rights. See Vonn, 535 U.S. at 62;
see also United States v. Bradley, 381 F.3d 641, 647 (7th Cir.
2004) (“Misunderstanding of the nature of the charge . . .
is not harmless error.”). That a plea be knowing and
voluntary is a “core concern” of Rule 11. United States v.
Pena, 314 F.3d 1152, 1157 (9th Cir. 2003). “[A] defendant’s
clear understanding of the nature of the charge to which
he is pleading guilty relates to the very heart of the
protections afforded by the Constitution and Rule 11.”
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 21
Fernandez, 205 F.3d at 1027. Looking at the totality of
the circumstances, we conclude that the variances from
Rule 11 that occurred during Mendoza’s plea colloquy
warrant vacatur of his conviction and a remand for
further proceedings.3
3
Mendoza also argues that his plea was not knowing and
voluntary because he did not have a clear understanding of the
mandatory minimum sentence he faced and that he never
actually pled guilty to responsibility for the requisite 500
grams or more of drugs to support that sentence. Because
we vacate the plea on other grounds, we need not reach this
argument. We note, however, that in this respect “Rule 11 only
requires that the court inform the defendant of the maximum
and minimum penalties . . . as well as the fact that the partic-
ular sentence imposed will be determined by reference to the
federal sentencing guidelines.” Blalock, 321 F.3d at 689 (holding
that plea was voluntary when court had not determined
drug amount at time of hearing, and told defendant amount
would be subsequently determined); see also Fed. R. Crim. P.
11(b)(1)(I). That requirement was satisfied here. The govern-
ment specifically referred to the potential five-year mandatory
minimum at the hearing, and Mendoza’s lawyer himself
clarified with the court that the drug amount was not being
established at that hearing, and instead would occur later
when the PSR was written. See, e.g., United States v. Wagner,
996 F.2d 906, 912 (7th Cir. 1993) (rejecting claim that plea
was involuntary on basis that specific amount had not been
determined, noting that parties had acknowledged exact drug
amounts would be calculated later).
22 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
B. Whether Facts Triggering Mendoza’s Mandatory
Minimum Sentence Needed to Be Proven Beyond
a Reasonable Doubt
Mendoza also appeals his sentence on the basis that a
jury, not a sentencing court, must find facts sufficient to
trigger the application of the mandatory minimum sen-
tence to which he was subjected. Because we are va-
cating Mendoza’s conviction on the basis set forth above,
we need not reach this issue. We note, however, that this
argument is foreclosed in the Seventh Circuit, because
our precedent is clear that judges may determine drug
amounts by a preponderance of the evidence that sub-
ject a defendant to a statutory mandatory minimum. See,
e.g., United States v. Clark, 538 F.3d 803, 811-12 (7th
Cir. 2008); United States v. Price, 516 F.3d 597, 605 (7th
Cir. 2008). Mendoza acknowledges this, but states in his
brief that he raises the issue to “preserve it for further
review” in light of the Supreme Court having granted
certiorari in United States v. O’Brien, 560 U.S. - - - -, 130
S. Ct. 2169 (2010) (the case has been decided since the time
Mendoza filed his brief). It is unclear why Mendoza
hedged a bet on the outcome of O’Brien. O’Brien
involved a provision of 18 U.S.C. § 924(c)—a statute not
at issue in this case—that provides for a 30-year man-
datory minimum sentence when the firearm used in
the offense is a machine gun. 18 U.S.C. § 924(c)(1)(B)(ii).
The O’Brien court ruled that the fact that a gun is a ma-
chine gun is an element of the § 924(c) offense that
must be proved to a jury beyond a reasonable doubt, as
opposed to a sentencing factor to be proven to the judge.
O’Brien, 130 S. Ct. at 2180. The holding has no bearing
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 23
on the validity of Mendoza’s sentence under 21 U.S.C.
§ 841(b)(1)(B). As we have repeatedly held, the amount
of drugs a defendant possessed is not an element of a
§ 841 offense and the sentencing judge can find facts
that trigger a mandatory minimum sentence. See Clark,
538 F.3d at 811-12; see also United States v. Washington, 558
F.3d 716, 720 (7th Cir. 2009); Price, 516 F.3d at 605.
Amount findings need be determined beyond a rea-
sonable doubt only when they implicate a statutory
maximum prison term, which is not the case here. See
United States v. Kelly, 519 F.3d 355, 363 (7th Cir. 2008);
see also Harris v. United States, 536 U.S. 545 (2002).
III. GERARDO PINEDA-SORIA—MOTION TO SUP-
PRESS
Gerardo Pineda-Soria was a supplier of cocaine to the
conspiracy. He pled guilty to possessing with intent
to distribute cocaine in violation of 21 U.S.C. § 841(a),
subject to a plea agreement in which he retained his
ability to appeal the district court’s denial of his mo-
tion to suppress drugs that had been found during a
search of his residence. He was sentenced to 30 months’
imprisonment. He now appeals the denial of his motion
to suppress.
When considering a motion to suppress, we review the
district court’s legal conclusions de novo, and factual
findings and credibility determinations for clear error.
United States v. Lewis, 608 F.3d 996, 999 (7th Cir. 2010). We
are particularly deferential to credibility findings, and
“unless the trial court has credited testimony that is
24 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
contrary to the laws of nature or so internally incon-
sistent or implausible on its fact that no reasonable
factfinder would credit it, we defer to the trial court’s
finding.” United States v. Collins, 604 F.3d 481, 486 (7th Cir.
2010).
A. The Search of Pineda-Soria’s Apartment
On June 18, 2008, Drug Enforcement Agency (“DEA”)
agents obtained a search warrant for Pineda-Soria’s
residence at 253 South High Street, Apartment A, in
Janesville, Wisconsin. The doorway of 253 South High
Street opens into a two-story foyer, and the building is
divided into two apartments, A and B. The entrance to
Apartment A is on the first floor, and an open staircase
leads up to the door for Apartment B. Neither door has
a letter, however, so it would not necessarily be clear
to someone that they were separate apartments. Based
on information that the upstairs apartment was empty,
agents limited their warrant application only to Apart-
ment A, and the warrant itself was similarly limited. An
arrest warrant for Pineda-Soria was issued at the same
time.
At 6:01 a.m. the next morning, DEA agents and Janes-
ville police officers executed the warrant. None of the
DEA agents that were aware of the Apartment A/B dis-
tinction were present at the search, and apparently had
not informed any of the searching officers that the
warrant was limited to the downstairs unit. Unaware of
the warrant’s limitation or the distinction between the
units, the entry team entered both Apartments A and B. In
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 25
performing a preliminary sweep of Apartment B, agents
found three men sleeping: Pineda-Soria, along with
Hoguer Pineda and Adrian Lazcano (the “co-tenants”). The
three were taken downstairs and outside. Pineda-Soria
was taken to the Janesville police station to be inter-
viewed, while Pineda and Lazcano remained on the
premises.
Before any contraband was found, a DEA agent
became aware that Apartment B was a separate unit
after speaking with residents of the downstairs unit.
Realizing the error, searching officers immediately
ceased the nascent search and withdrew to the front
lawn to wait for further instructions. It was decided to
ask Pineda-Soria and the co-tenants for consent to
search, and DEA agents also contacted an Assistant
United States Attorney regarding the possibility of ob-
taining another search warrant for Apartment B at the
same time.
At approximately 6:45 a.m., a Spanish-speaking Janes-
ville police officer asked each co-tenant separately
whether he would consent to a search of Apartment B.
Both men had by this point been allowed to get
dressed, and were not handcuffed. The interviewing
officer first asked the co-tenants if they lived in the
unit and both stated that they did. The officer then
told them it was up to them whether or not to allow a
search and both individually gave oral consent to
search. Police decided it would be advisable to also
obtain written consent from each co-tenant, and tele-
phoned another officer to bring a written consent form
26 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
that he could translate into Spanish for them to read
and sign.
In the meantime, at the Janesville police station, DEA
agents and police advised Pineda-Soria of his rights
and asked for his cooperation. He signed a Miranda
waiver form, and at 7:08 a.m. he filled out a written
consent form consenting to a search of Apartment B.
The record is not clear as to whether officers resumed
searching the upstairs unit once the co-tenants consented
at 6:45 a.m., or whether they also waited for Pineda-
Soria’s consent that came approximately 25 minutes
later. In any event, officers re-entered Apartment B, and
found a kilogram of cocaine under Pineda-Soria’s bed.4
By this time, agents had completed an initial inter-
view with Pineda-Soria, who had to that point denied
any involvement in the alleged conspiracy. When they
brought him back to the apartment building, they
learned that cocaine had been found in the search of
Apartment B. This update was shared with Pineda-Soria,
and he was reminded of his Miranda rights. Pineda-Soria
agreed to cooperate, and confronted with the evidence
that had been found, admitted to involvement in the
conspiracy.
Pineda-Soria moved to suppress the physical evidence
found in his apartment and the statements that he had
made, arguing that the search of Apartment B occurred
4
At some point during the search, a Spanish translation of
a written consent form was produced for the co-tenants,
which each signed at 7:40 a.m.
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 27
without a valid warrant and that there had been no
valid consent, and on December 8, 2008, an evidentiary
hearing was held. On February 11, 2009, a magistrate
judge issued a Report and Recommendation that the
district court deny the motion to suppress, finding
(1) that the consents to search Apartment B were valid,
and (2) that the inevitable discovery doctrine also ap-
plied. On March 5, 2009, the district court adopted the
Report and Recommendation and denied the motion to
suppress. Pineda-Soria then entered into a conditional
plea to one count of possessing with intent to distribute
cocaine, reserving his right to appeal the denial of his
motion to suppress.
B. Whether the Consents Were Voluntary
Pineda-Soria appeals the denial of his motion to sup-
press on two grounds. First, he argues that none of the
consents given to search Apartment B were voluntary.
Second, he asserts that the inevitable discovery doc-
trine should not apply, arguing that the government
failed to meet its burden of proof to benefit from
that doctrine.
No one disputes that the initial search of the upstairs
unit was illegal; officers entered Apartment B armed with
a warrant that only gave them permission to search
Apartment A. Nothing was found in the brief initial
sweep, however. It was not until officers re-entered the
unit, after receiving consent to do so, that contraband
was discovered. The Fourth Amendment’s warrant re-
28 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
quirement does not apply in circumstances where an
authorized party voluntarily consents to a search. United
States v. Parker, 469 F.3d 1074, 1077 (7th Cir. 2007); see
also Schneckloth v. Bustamonte, 412 U.S. 218, 219 (1973).
The relevant question here is whether the consents
from Pineda-Soria and his co-tenants to search Apart-
ment B were valid.5
Whether a defendant voluntarily consented to a search
is a question of fact determined by examining the
totality of the circumstances. Lewis, 608 F.3d at 999. In
making this determination, we consider (1) the de-
fendant’s age, intelligence, and education; (2) whether
the defendant was advised of his constitutional rights;
(3) how long the defendant was detained prior to
giving consent; (4) whether the consent was immediate,
or was prompted by repeated requests by authorities;
(5) whether any physical coercion was used; and
(6) whether the defendant was in police custody when
he gave his consent. United States v. Risner, 593 F.3d
692, 694 (7th Cir. 2010); see also United States v. Figueroa-
Espana, 511 F.3d 696, 704-05 (7th Cir. 2007). We review
5
While none of the officers on the scene were aware of the
warrant’s limitation to Apartment A, under the collective
knowledge doctrine the fact that some DEA agents were aware
of the distinction forecloses the good faith exception here. See
United States v. Harris, 585 F.3d 394, 400 (7th Cir. 2009). We
agree with the district court’s conclusion that the DEA’s
failure to properly inform or supervise the executing police
of this fact was reckless, meaning the exclusionary rule is in
play. Herring v. United States, 129 S. Ct. 695, 702 (2009).
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 29
a district court’s finding of voluntary consent for clear
error. United States v. Santiago, 428 F.3d 699, 704 (7th Cir.
2007). And when consent is given after an illegal search
has occurred, we must also be sure that the illegality
did not taint any consent that was given. To determine
whether the taint from an initial illegal search has been
purged, we examine (1) the temporal proximity of the
illegal entry and the consent; (2) the presence of inter-
vening circumstances; and (3) the purpose and flagrancy
of the official misconduct. Brown v. Illinois, 422 U.S. 590,
603-04 (1975); see also United States v. Robeles-Ortega, 348
F.3d 679, 681 (7th Cir. 2003). Viewing the circumstances
in light of these standards, we find that the consents
given in this case were valid and were not tainted by
the initial warrantless search, and that the district court
properly denied Pineda-Soria’s motion to suppress.
1. The Co-Tenants’ Consents
We first examine the consents given by the co-tenants,
Pineda and Lazcano. Approximately 45 minutes tran-
spired between the time that they were rousted out of
bed to when they gave their initial oral consent. They
were permitted to get dressed, initially sat on a couch
in Apartment A, then were relocated to the yard outside
of the house. They were not handcuffed, and were in
the company of other people that they knew. The record
is not clear on their age or education level, but we know
that officers communicated with them in their native
Spanish. When asked for consent, both co-tenants were
informed that they did not have to give permission, both
30 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
orally and on the written consent forms they signed. See
United States v. Valencia, 913 F.2d 378, 381 (7th Cir.
1990) (finding it significant that defendant had been
told he did not have to consent to search). The record
shows that each man gave his consent immediately, and
there is no evidence of repeated prodding or questioning
by police. While being awoken by armed officers and
made to leave their dwelling certainly must have been
an intimidating experience, there is no evidence that
any subsequent events took place that were coercive in
any way.
Nor do we think that the initial illegal entry tainted
the co-tenants’ consent in any way. Considering the
Brown factors, we find that the temporal proximity of
the illegal entry and consent, taken together with the in-
tervening circumstances, support the district court’s
finding that there was no taint. Brown, 422 U.S. at 603-04.
Forty-five minutes transpired between the time of the
illegal entry and the co-tenants’ verbal consents, and an
hour and forty minutes passed between the entry and
the written consent. See Valencia, 913 F.2d at 382. There
is no evidence of any coercion taking place during that
time; conversely, both Pineda and Lazcano were told
they did not have to consent if they did not want to.
Finally, consideration of the “purpose and flagrancy
of the official misconduct” weighs heavily in favor of
finding that any taint was purged. The initial entry into
Apartment B was a mistake on the part of the searching
officers, none of whom were aware of the limitation
on the warrant. Once the mistake was discovered, officers
immediately withdrew from the upstairs unit to deter-
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 31
mine what should be done next. The initial entry does not
appear to have been at all flagrant or purposeful, and it
did not taint the co-tenants’ subsequent consent. The
district court’s determination that the co-tenants’ con-
sents were voluntary is not clearly erroneous.
Pineda-Soria contends that even if the consents were
voluntary, neither co-tenant had any authority to actually
give it. By failing to object to the magistrate judge’s rec-
ommendation finding that they had authority, Pineda-
Soria has waived this issue on appeal. United States v.
Moore, 563 F.3d 583, 585 (7th Cir. 2009). And in any
event, the co-tenants did have apparent authority to
consent to the search. A police officer asked both men, in
Spanish, if they lived in the unit, and both answered
that they did. Pineda-Soria argues that officers have a
duty to inquire further as to a third party’s authority,
but that is only true when the circumstances make the
authority questionable in the first place. See United States v.
Goins, 437 F.3d 644, 649 (7th Cir. 2006). An officer can
conduct a search when the facts available at the time
“warrant a man of reasonable caution in the belief that the
consenting party had authority over the premises.” Illinois
v. Rodriguez, 497 U.S. 177, 188 (1990) (quotation omit-
ted). Here, the facts clearly warranted such a belief.
Pineda and Lazcano had authority to grant consent to
search Apartment B.
2. Pineda-Soria’s Consent
Having reached this conclusion, we need not address
the voluntariness of Pineda-Soria’s consent, but do so
32 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
anyway. We are more concerned with the voluntariness
of Pineda-Soria’s consent than we are with that of the
co-tenants. He was rousted out of bed and whisked
away to a police station for interrogation, and was thus
in a far more restrictive and potentially coercive setting
than the co-tenants were. And unlike the co-tenants,
Pineda-Soria was not on the premises and had no knowl-
edge of what was transpiring there. For all Pineda-
Soria knew, contraband could already have been found
at the location, and he may well have felt pressure to
appear cooperative and consent when he otherwise
would not have. See, e.g., Brown, 422 U.S. at 605 n.12. At
the same time, he was given Miranda warnings, spoken
to in his native Spanish, and chose to sign a written
consent form agreeing to the search. While the question
of the voluntariness of Pineda-Soria’s consent is a closer
call than that of his co-tenants, we are not “left with the
definite and firm conviction that a mistake has been
made” by the district court, and we find no clear
error in its finding that Pineda-Soria’s consent was also
voluntary. Lewis, 608 F.3d at 1000 (quotation and citation
omitted).
Having found that the district court did not err in con-
cluding that the consents from Pineda-Soria and the co-
tenants were valid, we need not reach the question of
whether the inevitable discovery doctrine would also
have justified the warrantless search. See United States v.
Patterson, 65 F.3d 68, 72 (7th Cir. 1995). We affirm
the district court’s denial of Pineda-Soria’s motion to
suppress the contraband found in his apartment and
the statements he made in connection therewith.
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 33
IV. ARTURO PINEDA-LOPEZ—COUNSEL’S MO-
TION TO WITHDRAW
Arturo Pineda-Lopez was another “runner” in the con-
spiracy and was overheard on wiretaps delivering
cocaine for Efrain Pineda-Buenaventura. Evidence
showed he delivered somewhere between 500 grams and
2 kilograms of drugs. He pled guilty pursuant to a
plea agreement to conspiracy to possess with intent
to distribute 500 grams of cocaine, in violation of 21
U.S.C. § 846. Pineda-Lopez’s PSR determined that he
had a base offense level under the sentencing guidelines
of 21, after a 3-level downward adjustment based on
acceptance of responsibility and a 2-level downward
adjustment because he met the “safety valve” provision,
18 U.S.C. § 3553(f). Coupled with a criminal history
category of I, Pineda-Lopez’s advisory guideline range
was 37-46 months. At sentencing, the district court gave
him the bottom of the range: 37 months. Pineda-Lopez’s
trial counsel has filed an Anders brief seeking permission
to withdraw on the basis that there are no non-
frivolous arguments to be made on appeal. See Anders v.
California, 386 U.S. 738 (1967).
Pineda-Lopez did not respond to his counsel’s submis-
sion, and so we review the potential issues counsel has
identified in his brief. See United States v. Garcia, 580
F.3d 528, 543 (7th Cir. 2009). Counsel represents that
Pineda-Lopez would challenge the reasonableness of
his sentence by arguing that his 37-month term is
unduly harsh in light of his limited involvement in the
conspiracy and his lack of criminal history. Counsel
34 Nos. 09-1500, 09-1525, 09-1875 & 09-2431
claims that while Pineda-Lopez may view the sentence
as harsh, it was well within the district court’s discretion
to impose it, and points out that the sentence is at
the bottom of the advisory guideline range. Therefore,
counsel argues, Pineda-Lopez’s argument would be
frivolous if raised on appeal.
Having reviewed the record and counsel’s Anders brief,
we agree. The court reviews the reasonableness of a
sentence under an abuse of discretion standard. United
States v. Poetz, 582 F.3d 835, 837 (7th Cir. 2009). We
apply a presumption of reasonableness to a sentence
that reflects proper application of the guidelines. Rita v.
United States, 551 U.S. 338, 347 (2007). Here, the sentence
was reasonable. The district court properly calculated
and considered the applicable Sentencing Guidelines
range, did not clearly err in its factual findings, and
imposed a sentence at the bottom of the range after con-
sidering the § 3553(a) factors. We conclude that there
are no non-frivolous issues on appeal, grant coun-
sel’s motion to withdraw, and dismiss Pineda-Lopez’s
appeal. See United States v. Recendiz, 557 F.3d 511, 534 (7th
Cir. 2009).
CONCLUSION
We V ACATE Teodulo Pineda-Buenaventura’s sentence
and R EMAND to the district court for resentencing con-
sistent with this opinion. We V ACATE Otoniel Mendoza’s
conviction and R EMAND for further proceedings. We
A FFIRM the district court’s denial of Gerardo Pineda-
Nos. 09-1500, 09-1525, 09-1875 & 09-2431 35
Soria’s motion to suppress. And we G RANT Pineda-Lopez’s
counsel’s motion to withdraw and D ISMISS his appeal.
9-15-10