United States v. Wooldridge

United States Court of Appeals
For the First Circuit
No. 15-1812
UNITED STATES OF AMERICA,
Appellee,
v.
JAMES DUNSTON,
Defendant, Appellant.
No. 15-1999
UNITED STATES OF AMERICA,
Appellee,
v.
SERGIO HERNANDEZ,
Defendant, Appellant.
____________________
No. 15-2000
UNITED STATES OF AMERICA,
Appellee,
v.
ANTHONY WOOLDRIDGE,
Defendant, Appellant.
_____________________
APPEALS FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MASSACHUSETTS
[Hon. Timothy S. Hillman, U.S. District Judge]
Before
Barron, Circuit Judge,
Souter, Associate Justice,
and Selya, Circuit Judge.
Peter J. Cyr, with whom Law Offices of Peter J. Cyr were on
brief, for appellant Wooldridge.
Michael D. Day, with whom The Day Law Firm, LLC was on brief,
for appellant Hernandez.
Xiomara M. Hernández on brief for appellant Dunston.
Mark T. Quinlivan, Assistant United States Attorney, with
whom Carmen M. Ortiz, United States Attorney, was on brief, for
appellee.
March 15, 2017

Hon. David H. Souter, Associate Justice (Ret.) of the Supreme
Court of the United States, sitting by designation.
SELYA, Circuit Judge. In cases in which defendants are
accused of trafficking in narcotics, drug quantity is often both
an element of the offense and a critical integer in the sentencing
calculus. These appeals illustrate that duality and, at the same
time, serve to explicate the shifting standards of proof that
pertain. Because the court below applied these standards
appropriately, we affirm both of the challenged convictions and
two of the three challenged sentences. With respect to the third
sentence, though, the government concedes that the district court
relied on too weak a foundation in classifying the defendant as a
career offender and we are not persuaded by the government's
attempt to brand the error harmless. We therefore remand that
sentence for further proceedings consistent with this opinion.
I. BACKGROUND
We start with an overview of the case, drawing relevant
facts from the trial transcripts, line sheets of recorded telephone
calls introduced into evidence, and (where appropriate) undisputed
portions of the defendants' presentence investigation reports.
This case has its roots in an investigation into drug
dealing in and around Worcester, Massachusetts, commenced by the
Drug Enforcement Administration (DEA) and local police officers.
The probe initially focused on defendants James Dunston and Sergio
Hernandez. Its scope later expanded to include defendant Anthony
Wooldridge.
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The investigation was launched with a number of
controlled buys: between January and June — all dates are in 2012
unless otherwise indicated — an undercover DEA agent bought nearly
forty-four grams of crack cocaine from Dunston and Hernandez in
sixteen separate transactions. Intelligence gained during these
sorties furnished the basis for properly authorized wiretaps on
both Hernandez's telephone and the telephone of yet another
coconspirator (Richard Cruz). Between June and September, the
agents intercepted close to 30,000 calls and text messages. The
wiretapped intercepts indicated that Dunston, Hernandez, and
Wooldridge were regularly dealing crack cocaine in Worcester and
its environs.
The wiretaps revealed, inter alia, that the defendants
acquired powder cocaine on no fewer than seven occasions in the
summer months and attempted at least one further acquisition.
Shortly after receiving the powder, the defendants promptly
converted it to crack. They frequently discussed crack conversion
techniques, described the results of particular conversions, and
boasted about their ability to convert powder to crack without
losing any appreciable drug weight.
It is said that all good things come to an end and, in
July, Wooldridge was arrested during a traffic stop after police
officers conducted a pat-frisk and found ninety-three grams of
crack cocaine on his person. Dunston and Hernandez were arrested
- 4 -
in September. All three were charged with conspiring to possess
with intent to distribute both crack cocaine and powder cocaine.
See 21 U.S.C. §§ 841(a)(1), 846. Additionally, Wooldridge was
charged with possession of crack cocaine with intent to distribute,
see id. § 841(a)(1), and Hernandez was charged with being a felon
in possession of a firearm and ammunition, see 18 U.S.C.
§ 922(g)(1).
After some preliminary skirmishing, all three defendants
waived indictment and pleaded guilty to superseding informations
charging them with, as relevant here, conspiring to possess with
intent to distribute crack cocaine. The informations specified
that the charged conspiracy "involved 280 grams or more of a
mixture and substance containing a detectable amount of cocaine
base" — a quantity sufficient to trigger a ten-year mandatory
minimum sentence. See 21 U.S.C. § 841(b)(1)(A)(iii).
Each defendant pleaded guilty to the underlying
conspiracy offense, reserving, however, the right to contest at a
bench trial whether the amount of crack cocaine reasonably
foreseeable or attributable to him was 280 grams or more (thus
exposing him to the mandatory minimum sentence). The district
court thereafter held an eight-day bench trial, at which it heard,
inter alia, recordings of intercepted calls as well as testimony
from a DEA agent (Timothy Boyle), who interpreted the slang and
jargon that permeated in the recordings. At the conclusion of all
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the evidence, the court found "beyond a reasonable doubt that over
280 grams of cocaine base [wa]s attributable and reasonably
foreseeable to all defendants."
The district court ordered the probation department to
prepare individual presentence investigation reports. At the
disposition hearings, the court adopted the reports without change
and classified all three defendants as career offenders under the
sentencing guidelines. It found Wooldridge responsible for at
least 840 grams of crack cocaine and sentenced him to a 132-month
term of immurement. With respect to Dunston and Hernandez, the
court found each of them responsible for at least 2.8 kilograms
(2,800 grams) of crack cocaine; sentenced Dunston to 144 months'
imprisonment; and sentenced Hernandez to 162 months' imprisonment.
These timely appeals followed.
II. ANALYSIS
The defendants' appeals have been consolidated, and we
turn first to the claims of error that implicate their convictions.
From that point, we proceed to their claims of sentencing error.
A. Lay Opinion Testimony.
Dunston contends that the district court should not have
allowed Agent Boyle to testify about the meaning of slang terms
and jargon used in the course of the wiretapped conversations. He
submits that although Boyle may have been qualified to give some
lay opinion testimony, the government failed to erect an adequate
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foundation for his interpretations of particular slang terms. To
illustrate his point, Dunston notes that Boyle was allowed to
testify that the word "tweezy" referred to crack cocaine and that
the phrase "step up a yard" referred to turning powder into crack.
In Dunston's view, Boyle's familiarity with the defendants'
conversations did not qualify him to give an informed opinion about
the meaning of these and other specific phrases used within those
conversations. We do not agree.
All three defendants raised this issue below, but only
Dunston pursues it on appeal. Objections to the admission of
evidence are reviewed for abuse of discretion. See United States
v. Valdivia, 680 F.3d 33, 50 (1st Cir. 2012). The parties agree
that Agent Boyle's testimony should be considered lay opinion
testimony. Hence, Federal Rule of Evidence 701 controls. See id.Rule 701 permits the admission of lay opinion testimony "rationally
based on the witness's perception" that would help the factfinder
"determin[e] a fact in issue."
Application of Rule 701 in the drug-trafficking context
is not novel: "we have long held that government witnesses with
experience in drug investigations may explain the drug trade and
translate coded language" for factfinders through lay opinion
testimony. United States v. Rosado-Pérez, 605 F.3d 48, 56 (1st
Cir. 2010); accord United States v. Hoffman, 832 F.2d 1299, 1310
(1st Cir. 1987) (holding that "interpretation of codes and jargon
- 7 -
used in the drug trade can be supplied through one experienced in
the field"). Such testimony is especially useful where, as here,
it can afford the factfinder the benefit of specialized knowledge.
See United States v. Albertelli, 687 F.3d 439, 446 (1st Cir. 2012).
Of course, such interpretive testimony must be anchored
in the witness's personal experience in the field, see Hoffman,
832 F.2d at 1310, and his experience-based understanding of the
meaning of the terms used, United States v. Prange, 771 F.3d 17,
28 & n.3 (1st Cir. 2014). Put another way, "an interpretation of
a phrase or reference ought to be explicable" — a standard that
typically requires the witness to point to similar statements
surrounding similar events. Albertelli, 687 F.3d at 450.
In the case at hand, the government erected a sturdy
foundation for Boyle's testimony. The record reflects that Boyle
had a twenty-four-year career in law enforcement, with significant
experience in undercover drug investigations. He had received
specialized training in narcotics enforcement, had participated in
over fifteen wiretap investigations, and had supervised more than
twenty other such investigations. As part of his duties, he had
reviewed audio and videotape from undercover crack cocaine
purchases "hundreds" of times and had taken part at least once in
an undercover operation in which he observed powder being converted
to crack.
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In this particular probe, Boyle reviewed nearly all of
the 30,000 calls and texts collected during the wiretaps. He not
only drew on his extensive experience to inform his understanding
of specific slang terms but also took into account the context in
which those terms were used. Boyle explained that he often
listened to "several calls leading up to" the use of a given bit
of slang as well as "conversations that would take place after
that" to ensure his understanding.
Confronted with objections, the district court prudently
allowed defense counsel to conduct a voir dire and question Boyle
about his credentials, his experience, and his knowledge. This
additional safeguard, coupled with Boyle's cross-examination by
all three defense attorneys, mitigated any risk of unfair prejudice
from his testimony. See United States v. Henry, ___ F.3d ___, ___
(1st Cir. 2017) [No. 15-2487, slip op. at 21]; Albertelli, 687
F.3d at 447.
Where malefactors try to mask their criminal activities
by using codes, a law enforcement officer who is equipped by
knowledge, experience, and training to break those codes can help
to inform the factfinder's understanding. So it is here: the
government provided the district court with ample reason to
conclude that Boyle was knowledgeable about the idiom of the drug
trade and, in particular, the vernacular of this group of
miscreants. On this record, we hold, without serious question,
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that the admission of Boyle's lay opinion testimony was comfortably
within the ambit of the district court's discretion.
B. Sufficiency of the Evidence.
The next leg of our journey takes us to Dunston's and
Wooldridge's claims that the district court lacked sufficient
evidence to find them guilty of the charged offense. These claims
share a common focus: they are aimed at the district court's
finding, at trial, that at least 280 grams of crack cocaine was
"attributable and reasonably foreseeable" by the defendant making
the claim. Such a defendant-specific finding is an element of the
offense of conviction: it means that a defendant cannot, simply by
reason of his membership in a conspiracy that traffics in large
amounts of drugs, automatically be "saddled with the full weight
of the conspiracy's wrongdoing." United States v. Sepulveda, 15
F.3d 1161, 1197 (1st Cir. 1993). He can only be held responsible
for drugs that he "personally handled or anticipated handling," as
well as "drugs involved in additional acts that were reasonably
foreseeable by him and were committed in furtherance of the
conspiracy." Id.Here, the district court held a bench trial on the drug-
weight issue — a trial that was necessary because any fact that
increases the mandatory minimum sentence for an offense must,
absent a plea or a stipulation, be submitted to a factfinder to be
determined beyond a reasonable doubt. See Alleyne v. United
- 10 -
States, 133 S. Ct. 2151, 2155 (2013) (citing Apprendi v. New
Jersey, 530 U.S. 466, 483 n.10, 490 (2000)); United States v.
Pizarro, 772 F.3d 284, 292-93 (1st Cir. 2014). At the end of the
trial, the court found that each of the defendants was responsible
for at least 280 grams of crack cocaine.
Hernandez does not appeal the drug-quantity
determination as it relates to him. Dunston and Wooldridge do
appeal and, as to each of them, we must "examin[e] the facts and
inferences in the light most favorable to the verdict." United
States v. O'Donnell, 840 F.3d 15, 18 (1st Cir. 2016) (citation
omitted); cf. United States v. Colon-Solis, 354 F.3d 101, 103 (1st
Cir. 2004) (requiring "defendant-specific determination of drug
quantity" for this purpose). The ultimate question is whether,
after viewing the evidence in the light most hospitable to the
government, a rational trier of fact could have found the drug-
weight elements beyond a reasonable doubt. See United States v.
Grace, 367 F.3d 29, 34 (1st Cir. 2004). We must answer this
question separately as to each of the two appealing defendants,
see Colon-Solis, 354 F.3d at 103, exercising de novo review. See
O'Donnell, 840 F.3d at 18.
With this preface, we turn to the substance of the
sufficiency claims. We begin with Dunston and then move to
Wooldridge.
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1. Dunston. Dunston contends that the court's finding
that he was responsible for at least 280 grams of crack cocaine
was plucked out of thin air. Pointing out that the authorities
never seized any of the drugs to which he alluded in the wiretapped
conversations, he insists that it remains unclear how much powder
was converted to crack.
Dunston is whistling past the graveyard. The government
presented evidence linking Dunston to at least eight separate
transactions. We need examine only two of these occurrences to
defuse Dunston's attack.
On June 26, the government intercepted a telephone call
in which Dunston and Hernandez discussed their plans to cook 200
grams of powder cocaine recently purchased from Wooldridge. The
two men split the contraband, and Dunston told Hernandez that he
was going to "step up a yard right now and see what it is." This
meant, Agent Boyle testified, that Dunston intended to convert 100
grams of powder into crack. Later that day, Dunston and Hernandez
spoke again. When Hernandez asked, "how did that come out,"
Dunston replied that the result was "[a]ll yellow" and that he
"[g]ot back, like, 2 extra grams. It was, like, 102 when it dried
all the way out, bone dry." Boyle testified that the yellow tinge
of Dunston's product was emblematic of crack cocaine and that,
since converting powder to crack requires water, Dunston's
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reference to drying the product was also consistent with making
crack.
When judges sit as factfinders, they are not obliged to
put their common sense into cold storage. Given the wiretaps and
Boyle's testimony, the district court surely had a rational basis
for finding, beyond any reasonable doubt, that Dunston was
responsible for at least 200 grams of crack stemming from the June
26 events. For one thing, the court supportably could have found
Dunston responsible for the 100 grams that he himself cooked. For
another thing, the court supportably could have found that the
remaining 100 grams, retained by Hernandez, was to be converted
from powder to crack as part of the conspiracy and that the
conversion was reasonably foreseeable to Dunston.1
Dunston protests. He says that there is no evidence
that this latter 100 grams of powder was actually converted to
crack and that this part of the district court's drug-quantity
calculation was faulty because it implicitly assumed that 100 grams
of powder cocaine, when converted, would yield 100 grams of crack
1For example, the court heard evidence that once Dunston told
Hernandez that he "got back 2 . . . extra grams" after cooking the
powder, Hernandez responded, "You should have done mine." Dunston
replied, "You're the only one that didn't want me to do yours!"
and indicated that Hernandez had mentioned planning to cook his
powder in a particular type of pot. Several hours later, Hernandez
called a third party and asked to use his kitchen.
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cocaine. He insists that, even in optimal conditions, 100 grams
of powder cannot be converted into more than 89.2 grams of crack.
This attack misfires. The court had before it evidence
that, on both June 26 and June 29 (discussed infra), Dunston
himself had performed conversion operations and had gotten better
than a one-to-one yield. Given that evidence, the court was
entitled to apply a one-to-one conversion ratio in its appraisal
of the conspiracy's output.2
The court also heard the particulars of a transaction
that occurred on June 29. On that date, the government intercepted
a call between Hernandez and a third party, during which Hernandez
bought 200 grams of powder cocaine. Just over two hours later,
Dunston called Hernandez to inform him that he planned to "do the
whole thing together." He subsequently reported that the result
was "206 wet," and yellow in color, but quickly turning white.
Given this evidence and Boyle's explanatory testimony, the
district court could have attributed, beyond any reasonable doubt,
an additional 200 grams of crack to Dunston. After all, proof
2
We note, moreover, that the statute of conviction
criminalizes conspiracies involving the possession and intended
distribution of "280 grams or more of a mixture or substance
. . . which contains cocaine base." 21 U.S.C. § 841(b)(1)(A)(iii)
(emphasis supplied). Whether the weight of the defendants'
products came from pure crack cocaine or crack combined with water
or some other adulterant is beside the point: the record reflects
that the defendants conspired to possess and distribute a "mixture
or substance" that contained cocaine base. Id.- 14 -
beyond a reasonable doubt does not require proof to an absolute
certainty. See United States v. Lasseque, 806 F.3d 618, 623 (1st
Cir. 2015), cert. denied, 136 S. Ct. 1472 (2016).
Dunston counters that the government offered no direct
or tangible evidence that this batch of cocaine ever existed. But
it is old hat that proof of a defendant's guilt can be based, in
whole or in part, on circumstantial evidence. See United States
v. George, 841 F.3d 55, 63 (1st Cir. 2016); United States v.
Williams, 717 F.3d 35, 39-40 (1st Cir. 2013). In this instance,
the district court, qua factfinder, drew a series of reasonable
inferences from the evidence, and its conclusion that Dunston was
responsible for this additional 200 grams of crack is unimpugnable.
For these reasons, Dunston's conviction must stand.
2. Wooldridge. The record also provides ample support
for the district court's decision to attribute at least 280 grams
of crack cocaine to Wooldridge. Wooldridge was arrested with
ninety-three grams of crack on his person. In addition, there was
cogent evidence that Wooldridge sold his codefendants the 200 grams
of powder cocaine mentioned in the June 26 conversation. As
explained above, 200 grams of powder could be found, beyond a
reasonable doubt, to equal 200 grams of crack. Because the
production of crack was a reasonably foreseeable act in furtherance
of the conspiracy, the district court did not err either in finding
that Dunston and Hernandez converted their shares of the powder
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sold by Wooldridge into crack or in holding Wooldridge responsible
for a corresponding amount of crack. See Sepulveda, 15 F.3d at
1197.
In an effort to stave off this conclusion, Wooldridge
insists that he was not yet part of the charged conspiracy when he
sold drugs to his codefendants at the end of June. Building on
that foundation, he posits that any crack cocaine resulting from
that sale cannot be attributed to him. This is revisionist
history, and we reject it. Wooldridge pleaded guilty to being a
member of the conspiracy beginning in August of 2011 — long before
the sale occurred. He is bound by his plea. See United States v.
Laracuent, 778 F.3d 347, 351 (1st Cir.), cert. denied, 135 S. Ct.
2875 (2015).
That ends this aspect of the matter. We conclude that
the evidence was sufficient to allow the district court to find
beyond a reasonable doubt that at least 280 grams of crack were
attributable to Wooldridge. Consequently, his conviction must
stand.
C. Dunston's Sentence.
Dunston's claim of sentencing error is easily
dispatched. He does not challenge the district court's guideline
calculations but, rather, maintains that his 144-month sentence
offends the parsimony principle, see United States v. Sepúlveda-
Hernández, 817 F.3d 30, 34 (1st Cir. 2016) (citing 18 U.S.C.
- 16 -
§ 3553(a)), because it is greater than necessary to achieve the
purposes of sentencing. Under our case law, we treat such a claim
as one of substantive unreasonableness. See id.
Dunston did not raise this claim in the district court,
and the standard of review is unsettled. See United States v.
Ruiz-Huertas, 792 F.3d 223, 228 (1st Cir.) (noting uncertainty
with respect to standard of review regarding unpreserved claims of
substantive unreasonableness), cert. denied, 136 S. Ct. 258(2015). For simplicity's sake, we assume — favorably to Dunston
— that review is for abuse of discretion.
Dunston was subject to the career offender guideline.
See USSG §4B1.1(a). The court below set his guideline sentencing
range (GSR) at 262-327 months and sentenced him appreciably below
the bottom of that range. A defendant who challenges a below-the-
range sentence as substantively unreasonable must carry a heavy
burden. See United States v. Montero-Montero, 817 F.3d 35, 37
(1st Cir. 2016). The greater the drop from the bottom of the
range, the heavier the lift. See id.There is more than one reasonable sentence in any given
case, and the relevant inquiry is whether the sentence imposed
"resides within the expansive universe of reasonable sentences."
United States v. King, 741 F.3d 305, 308 (1st Cir. 2014). In
mounting this inquiry, we concentrate on whether the sentence
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reflects "a plausible . . . rationale and a defensible result."
United States v. Martin, 520 F.3d 87, 96 (1st Cir. 2008).
The court below supplied a plausible rationale for
Dunston's sentence. It explained that a significant period of
incarceration was warranted to protect the public from future
crimes, provide deterrence, and punish the defendant. Given the
scope and duration of the conspiracy, the force of this explanation
cannot be gainsaid. The court added, though, that "incarceration
at or near the advisory guideline range seems to be more than what
is necessary to meet the goals of sentencing." For that reason,
it executed a sharp downward variance.
Despite the court's seeming leniency, Dunston assails
the result, arguing that his ultimate sentence was skewed by a
"mechanical application" of the career offender guideline. This
argument is constructed out of whole cloth: it overlooks the
undeniable fact that the sentencing court's downward variance was
anything but mechanical, yielding a sentence almost ten years below
the nadir of the guideline range. The challenged sentence, which
took into account the nature of Dunston's crime, his history, and
his personal characteristics, was wholly defensible and well
within the court's discretion. See King, 741 F.3d at 309.
D. Wooldridge's Sentence.
Wooldridge challenges the amount of crack cocaine
attributed to him for sentencing purposes. This drug quantity (at
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least 840 grams) is separate from the lesser drug quantity (280
grams) needed to establish Wooldridge's guilt. See supra Part
IIB. We explain briefly why two distinct findings are necessary.
At trial, the government had the burden of proving the
drug quantity charged as an element of the offense (280 grams or
more) beyond a reasonable doubt. See Alleyne, 133 S. Ct. at 2155.
At sentencing, however, "a defendant-specific determination of
drug quantity [i]s a benchmark for individualized sentencing under
the guidelines." Colon-Solis, 354 F.3d at 103. The sentencing
court is charged with making such a defendant-specific
determination. See United States v. Correy, 773 F.3d 276, 279-
80, 280 n.4 (1st Cir. 2014). All drugs "attributable to[] or
reasonably foreseeable by" a defendant may be included in that
defendant's individualized total. United States v. Cintrón-
Echautegui, 604 F.3d 1, 5 (1st Cir. 2010). The government bears
the burden of proving drug quantity at sentencing by a
preponderance of the evidence. See id. at 6.
The sentencing guidelines direct a sentencing court to
consider relevant conduct, see USSG §1B1.3(a), when assessing the
drug quantity for which a defendant is to be held accountable at
sentencing. Where, as here, a defendant has been convicted as a
coconspirator, his relevant conduct includes not only his own acts
and omissions but also the reasonably foreseeable acts and
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omissions of other coconspirators in furtherance of the
conspiracy. See id. §1B1.3(a)(1)(B).
A sentencing determination of defendant-specific drug
quantity does not require mathematical precision: it need only be
a "reasonable approximation of the weight of the controlled
substance(s) for which the defendant should be held responsible."
United States v. Demers, 842 F.3d 8, 12 (1st Cir. 2016). As we
have said, calculating drug quantities "is not an exact science,"
and the sentencing court "need not be precise to the point of
pedantry." United States v. Platte, 577 F.3d 387, 392 (1st Cir.
2009).
Such drug-quantity determinations are quintessentially
factual in nature, and we review them for clear error. See
Cintrón-Echautegui, 604 F.3d at 6. That standard dictates that a
finding will stand unless a reviewing court, after assessing the
whole of the record, is firmly convinced that a mistake has been
made. See id. "[W]here there is more than one plausible view of
the circumstances, the sentencing court's choice among supportable
alternatives cannot be clearly erroneous." United States v. Ruiz,
905 F.2d 499, 508 (1st Cir. 1990).
Against this backdrop, Wooldridge argues that the
district court committed clear error in finding him accountable
for at least 840 grams of crack cocaine. That finding, combined
with other uncontroversial guideline calculations and Wooldridge's
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designation as a career offender, see USSG §4B1.1(a), resulted in
a GSR of 262-327 months. The district court proceeded to impose
a below-the-range sentence of 132 months.
Although the district court varied downward from the
guideline range, any error in calculating that range would likely
be material on appeal. See Molina-Martinez v. United States, 136
S. Ct. 1338, 1346 (2016) ("In most cases a defendant who has shown
that the district court mistakenly deemed applicable an incorrect,
higher Guidelines range has demonstrated a reasonable probability
of a different outcome."). Here, however, the district court's
drug-quantity determination (and, thus, its configuration of the
GSR) is not clearly erroneous.
The district court identified three transactions that
linked Wooldridge to well over 840 grams of crack cocaine. First,
Wooldridge sold powder cocaine to Hernandez and Dunston at the end
of June and, as discussed above, see supra Part IIB, that sale
formed a solid basis for a finding attributing approximately 200
grams of crack cocaine to him. Second, the court supportably tied
Wooldridge to a purchase of 300 grams of powder cocaine that
occurred on July 31.3 The record includes discussions among all
three defendants about the purchase and about their plans to
3 Indeed, Wooldridge admits that the ninety-three grams of
crack cocaine found on his person when he was arrested was his
share of this purchase.
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convert the powder into crack. That evidence, coupled with the
court's permissible use of a one-to-one conversion ratio, was
sufficient to ground attribution of 300 grams of crack cocaine to
Wooldridge.
Third, and finally, the court reasonably attributed an
additional 497 grams of crack cocaine to Wooldridge with respect
to events occurring on August 31. At that time, federal agents
seized a package sent by Cruz (in Puerto Rico) to an acquaintance
of Hernandez (in Massachusetts). The package was found to contain
497 grams of powder cocaine. Although the evidence indicated that
Hernandez was the prime mover in arranging for the shipment, both
Wooldridge and Dunston encouraged his efforts. Thus, the 497 grams
of powder cocaine, destined for conversion into crack cocaine,
could fairly be attributed to Wooldridge for sentencing purposes.
See Cintrón-Echautegui, 604 F.3d at 5; USSG §1B1.3(a)(1)(B).
The fact that the package was intercepted before its
contents reached the defendants is of no moment. The record makes
manifest that the defendants, in furtherance of the conspiracy,
sought the shipment of powder cocaine as a prelude to conversion
and would in all probability have converted it to crack cocaine if
given the chance. Indeed, the government introduced evidence
showing that, on no fewer than seven separate occasions between
June and August, the defendants procured powder cocaine and
converted it into crack cocaine within a matter of days. When
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drug traffickers have forged a well-defined pattern and practice
for their operations, a sentencing court need not turn a blind eye
to that pattern and practice.
Wooldridge tries to distance himself from this drug
weight, asseverating that no part of the August 31 shipment should
be attributed to him because his coconspirators had "cut[] [him]
out of the picture" by then. But the evidence of exclusion is
meager, and the district court was not obliged to resolve this
issue in Wooldridge's favor. Just as withdrawal from a conspiracy
requires more than an empty claim of disaffection, see United
States v. Piper, 298 F.3d 47, 53 (1st Cir. 2002) (explaining that,
in order to withdraw, a conspirator must take affirmative action
to disavow or defeat the conspiracy), so too does a claim of
exclusion. There is simply no credible evidence that either
Wooldridge or his partners in crime took any such action here. To
the contrary, the record reflects that Wooldridge contacted
Hernandez at the end of July in search of cocaine and exhibited an
abiding intent to remain involved in the conspiracy. Given the
absence of any competent evidence of withdrawal, the sentencing
court did not clearly err in finding the coconspirators' acts at
the end of August to be a part of Wooldridge's relevant conduct.
E. Hernandez's Sentence.
Hernandez's claim of sentencing error similarly embodies
a challenge to the district court's drug-quantity determination.
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The court found him responsible for at least 2.8 kilograms of crack
cocaine. Combined with other uncontroversial guideline
calculations and a career offender enhancement, this drug quantity
resulted in a GSR of 292-365 months. The district court imposed
a below-the-range sentence of 162 months.
The record is replete with circumstantial evidence that
Hernandez headed up the conspiracy. He was involved in every
transaction that we have discussed: the events of June 26 (200
grams), the events of June 29 (200 grams), the events of July 31
(300 grams), and the events of August 31 (497 grams). In
consequence of this involvement, 1,197 grams of crack cocaine were
fairly attributable to him.
Furthermore, the record contains proof sufficient to
support the attribution to Hernandez, using a one-to-one
conversion ratio, of an additional 1,000 grams of crack cocaine:
 200 grams of powder cocaine purchased and converted on July
7;
 100 grams of powder cocaine converted on July 15;
 500 grams of powder cocaine purchased on August 5 and
converted the following day; and
 200 grams of powder cocaine purchased on August 28 and at
least partially converted the next day.
When these quantities are combined with the nearly forty-four grams
of crack sold by Hernandez to undercover officers at the start of
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the probe, Hernandez can properly be held responsible for a minimum
of 2.2 kilograms of crack cocaine.
To boost that total to 2.8 kilograms, the district court
reasonably relied on two additional events. First, the evidence
showed that, on July 29, Hernandez arranged the payment of $19,000
to Cruz for powder cocaine previously supplied. The court
supportably concluded that this payment represented the purchase
of roughly 500 grams of powder cocaine. See Sepulveda, 15 F.3d at
1201 (holding that when cash is likely dedicated to the purchase
of contraband, "a sentencing court may convert the cash into
equivalent amounts of narcotics" for sentencing purposes). After
applying a one-to-one conversion ratio, this transaction yielded
500 grams of crack cocaine attributable to Hernandez.
The court reasonably added another 100 grams, based on
evidence that Hernandez was actively dealing crack cocaine between
January and June (when the wiretaps were instituted). While this
finding represented an estimate, it was by all odds a conservative
estimate — especially since Hernandez pleaded guilty to conspiring
to deal crack as early as August of 2011. We have consistently
upheld a sentencing court's use of reasonable estimates in
assessing drug quantity, see, e.g., United States v. Bernier, 660
F.3d 543, 546 (1st Cir. 2011); Platte, 577 F.3d at 392; United
States v. Ventura, 353 F.3d 84, 88 (1st Cir. 2003), and that praxis
has particular appeal when — as in this case — the sentencing
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court, in fashioning its estimate, has taken a conservative
approach, cf. United States v. Sklar, 920 F.2d 107, 113 (1st Cir.
1990) (admonishing sentencing courts, in this context, to "err on
the side of caution" (citation omitted)).
This gets the grease from the goose. While we could
analyze these multiple transactions in more granular detail, doing
so would serve no useful purpose. It suffices to say that the
record discloses ample evidence to ground a finding that Hernandez
was responsible for at least 2.8 kilograms of crack cocaine. As
a result, we discern no clear error in the district court's drug-
quantity determination.
Hernandez has one last string to his bow. He takes issue
with the district court's designation of him as a career offender
under the sentencing guidelines. Specifically, he asserts that
the court improperly relied, over objection, on a portion of his
presentence investigation report, which cited only criminal
offender record information (CORI) to lay out his criminal history.
The government bears the burden of establishing the
existence of at least two predicate offenses to trigger a career
offender enhancement under the sentencing guidelines. See United
States v. Bryant, 571 F.3d 147, 153 (1st Cir. 2009) (citing USSG
§4B1.1(a)). The government may carry this burden in divers ways,
such as by furnishing "a certified copy of the conviction or an
equivalent proffer" or by pointing to official court documents of
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the type that engender a presumption of reliability. Id. at 153,
155 (quoting United States v. McKenzie, 539 F.3d 15, 19 (1st Cir.
2008)). But anecdotal CORI descriptions, if objected to, are not
enough. See id. at 154-55; cf. United States v. Brown, 510 F.3d
57, 74 (1st Cir. 2007) (observing that "when a defendant challenges
a conviction laid out in the [presentence investigation report],
more is required").
At Hernandez's sentencing, the government argued for a
career offender enhancement noting that the CORI material
described in the presentence investigation report identified three
potential predicate offenses. Hernandez objected. The district
court stayed the proceedings to give the government the opportunity
to make a more persuasive evidentiary proffer; but when the
government produced nothing more, the court overruled Hernandez's
objection and sentenced him as a career offender.
On appeal, Hernandez insists that the record before the
district court was insufficient to show the required predicate
offenses. The government concedes this point and instead proffers
a series of docket sheets, never made available to the district
court, inviting us to take judicial notice of them. These docket
sheets, it says, will confirm the existence of the required
predicate offenses (albeit belatedly) and render any error
harmless.
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We decline the government's invitation. As a general
matter, we do not consider evidentiary materials that were not
proffered in the district court. See United States v. Farrell,
672 F.3d 27, 30-31 (1st Cir. 2012); United States v. Kobrosky, 711
F.2d 449, 457 (1st Cir. 1983). Although we have occasionally taken
judicial notice of state court documents identified for the first
time on appeal, see, e.g., Farrell, 672 F.3d at 31; United States
v. Mercado, 412 F.3d 243, 247-48 (1st Cir. 2005), we cannot do so
here. The proffered documents bear no hallmarks of authenticity
and, in all events, are subject to interpretation. A career
offender designation can expose a defendant to a significantly
higher sentence, and it remains the district court's duty to ensure
that documents offered to prove the existence of predicate offenses
are "sufficiently reliable." Bryant, 571 F.3d at 154.
Although we conclude that the district court erred, we
think it would be premature to vacate Hernandez's sentence.
Instead, we remand so that the district court may hold a hearing
and afford the parties an opportunity to present evidence anent
Hernandez's prior convictions. Should the district court find
that the evidence presented is sufficiently reliable and
establishes the existence of the requisite number of predicate
offenses, it should, within sixty days from the date hereof, report
its findings and conclusions to this court. If, however, the court
finds to the contrary, it should, within sixty days from the date
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hereof, report its findings and conclusions to this court and
proceed to vacate Hernandez's sentence and resentence him without
reference to the career offender guideline.
III. CONCLUSION
We need go no further. For the reasons elucidated above,
we affirm the judgment in appeal number 15-1812, thus affirming
Dunston's conviction and sentence. We likewise affirm the judgment
in appeal number 15-2000, thus affirming Wooldridge's conviction
and sentence. With respect to appeal number 15-1999 (Hernandez),
we remand for further proceedings consistent with this opinion and
for the time being retain appellate jurisdiction over this appeal.
So ordered.
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