United States v. Bryant, Thomas

In the
United States Court of Appeals
For the Seventh Circuit
No. 07-3608
U NITED S TATES OF A MERICA,
Plaintiff-Appellee,
v.
T HOMAS B RYANT,
Defendant-Appellant.
Appeal from the United States District Court
for the Northern District of Illinois, Eastern Division.
No. 05 CR 71—Elaine E. Bucklo, Judge.
A RGUED O CTOBER 21, 2008—D ECIDED F EBRUARY 26, 2009
Before R IPPLE, E VANS and SYKES, Circuit Judges.
R IPPLE, Circuit Judge. On April 8, 2005, Thomas Bryant
provided Eddie Franklin with a substance containing
cocaine base. Franklin delivered that substance to a
confidential informant, who then turned the sample over
to the Government. Mr. Bryant was subsequently
arrested and charged with one count of conspiracy to
distribute cocaine base. Mr. Bryant initially pleaded
guilty to the charge, but later unsuccessfully sought to
withdraw his guilty plea. At his sentencing hearing, the
2 No. 07-3608
district court sentenced Mr. Bryant to 180 months’ impris-
onment. Mr. Bryant now challenges the district court’s
denial of his motion to withdraw his guilty plea. He
also raises several challenges to the sentence imposed by
the district court. For the reasons set forth in this opinion,
we affirm the district court’s denial of his motion to
withdraw his plea, vacate his sentence and remand for
resentencing.
I
BACKGROUND
A.
In 2005, a confidential informant contacted Eddie Frank-
lin and attempted to purchase crack cocaine. Franklin
agreed to obtain crack for the informant and called the
defendant, Thomas Bryant, in an attempt to procure the
drugs. On April 8, 2005, Mr. Bryant provided Franklin
with a substance that Franklin described as hard and rock-
like. Franklin then delivered the substance to the infor-
mant, who turned it over to Drug Enforcement Adminis-
tration (“DEA”) agents.
A DEA chemist analyzed the substance and, in his report,
described it as a beige, compressed, moist powder. Al-
though the substance tested positive for the presence of
cocaine base, the chemist did not detect the presence of
No. 07-3608 3
sodium bicarbonate in the substance.1 Later, a second
DEA chemist analyzed the substance, described it as
hard and rock-like and concluded that it contained
sodium bicarbonate. After the second chemist completed
his analysis, the Government discovered that he had
mishandled evidence on several occasions during the
time period in which he analyzed the substance at issue
here. The Government decided that, because chain of
custody issues may have resulted from the chemist’s
mishandling of evidence, it would introduce neither the
substance nor the second chemist’s report in its case
against Mr. Bryant.
B.
Several months after Franklin delivered the substance
to the informant, the Government arrested Mr. Bryant and
Franklin. Mr. Bryant subsequently entered a blind condi-
tional guilty plea to one count of conspiracy to distribute
cocaine base; he reserved the issues of the type and quan-
tity of the drugs involved for a bench trial. At the time
of his plea, he was aware that the first DEA chemist’s
description of the substance conflicted with Franklin’s
description. He believed, however, that the second DEA
chemist’s report would corroborate Franklin’s description
1
The presence of sodium bicarbonate in a mixture containing
cocaine base is one of the indicators that the mixture is crack
cocaine.
4 No. 07-3608
of the substance.2 At the time of his plea, Mr. Bryant was
unaware that the second chemist had mishandled evi-
dence.
On October 27, 2006, Mr. Bryant moved to withdraw
his plea. He claimed that he had been pressured into
accepting the plea by his former attorney, who had
stated that he was unprepared for trial. Mr. Bryant did not
claim that he was innocent of the crime charged; rather,
he indicated that he did not believe that the Govern-
ment could prove its case beyond a reasonable doubt.
The district court held a plea withdrawal hearing, during
which both Mr. Bryant and his former attorney testified.
The district court noted that Mr. Bryant’s statements
conflicted with his former attorney’s statements. It con-
cluded that Mr. Bryant had intentionally misled the
court and denied Mr. Bryant’s motion to withdraw his
plea.
Mr. Bryant asserts that, immediately prior to his
bench trial, he made a second motion to withdraw his
plea on the basis of newly discovered evidence.3 He con-
2
The first DEA chemist to analyze the substance described it
as a beige, compressed, moist powder. Both the second DEA
chemist and Franklin described the substance as hard and rock-
like.
3
The Government contends that Mr. Bryant did not move to
withdraw his plea; rather, it claims, he requested additional
time “to figure it out and determine whether it matters.” R.183-9
at 6. The Government characterizes Mr. Bryant’s statements
(continued...)
No. 07-3608 5
tended that he should be allowed to withdraw his plea
on the ground of newly discovered evidence in light of the
Government’s discovery that the second chemist had
mishandled evidence and its decision that it would not
introduce the substance or the second DEA chemist’s
report. The district court rejected this argument. It con-
cluded that Mr. Bryant would not have altered his
decision had he known that the second chemist mishan-
dled evidence because Mr. Bryant “necessarily challenged
[the chemist’s] finding by saying he wasn’t going to
agree that it was crack.” R.183-9 at 17.
On August 3, 2007, the district court held a bench trial
to determine the type and quantity of drugs involved in
the conspiracy.4 Franklin testified that he had purchased
3
(...continued)
as an emergency motion to continue the bench trial. Statements
made by the district court support this characterization. R.183-9
at 18 (“I’m not going to continue [the trial], not for that rea-
son.”).
Although Mr. Bryant claims to have made a motion to
withdraw his plea, there is no indication that he expressly
requested that his plea be withdrawn. Nevertheless, because
Mr. Bryant asserted that he should have “known about [the
evidentiary problems] so [he] could have figured this out
while [he] still had time,” id. at 6, we shall assume, for the
purposes of this appeal, that Mr. Bryant moved to withdraw
his plea.
4
The issue of the type and quantity of drugs involved in the
charged crime was litigated on two occasions in the pro-
ceedings before the district court: First, in order to determine
(continued...)
6 No. 07-3608
crack from Mr. Bryant on numerous occasions. He re-
counted the details of the April 8 transaction, stating that
he received about sixty-three grams of crack cocaine
from Mr. Bryant. He described the substance he received
4
(...continued)
the statutory maximum sentence, the court held a bench trial to
determine whether the Government had proven, beyond a
reasonable doubt, that Mr. Bryant had conspired to distribute
five kilograms or more of a mixture containing cocaine or fifty
grams or more of a mixture containing cocaine base. 21 U.S.C.
§ 846 (“Any person who attempts or conspires to commit any
offense defined in this subchapter shall be subject to the same
penalties as those prescribed for the offense, the commission
of which was the object of the attempt or conspiracy.”); 21
U.S.C. §§ 841(b)(1)(A)-(C) (establishing statutory maximum
and minimum sentences for the crime of possession with
intent to distribute a controlled substance). As we previously
have noted, “all facts . . . that set the maximum possible punish-
ment under § 841(b) must be established beyond a reasonable
doubt to the satisfaction of the same body that determines
culpability under § 841(a).” United States v. Brough, 243
F.3d 1078, 1079 (7th Cir. 2001) (citing United States v. Nance, 236
F.3d 820 (7th Cir. 2000)). Next, the district court held a sentenc-
ing hearing to determine the type and quantity of the drugs
involved in the charged conspiracy; at that hearing, “[t]he
government [had] the burden of proving the quantity of drugs
attributable to [the] defendant for sentencing purposes by a
preponderance of the evidence.” United States v. Krasinski,
545 F.3d 546, 551 (7th Cir. 2008) (citing United States v. Soto-
Piedra, 525 F.3d 527, 529 (7th Cir. 2008)).
No. 07-3608 7
on that date as hard and rock-like.5 The district court
concluded, based on the discrepancy between the first
DEA chemist’s description of the substance and
Franklin’s description of the substance, that the Govern-
ment had failed to prove, beyond a reasonable doubt, that
Mr. Bryant had conspired to distribute crack cocaine.
R.144.
At Mr. Bryant’s sentencing hearing, the district court
found, based on the testimony presented at the bench
trial, 6 that the Government had proven, by a preponderance
of the evidence, that Mr. Bryant had conspired to
distribute more than fifty grams of crack cocaine. The
court therefore assigned Mr. Bryant a base offense level
of 30 under the November 2007 Amendments to the
Sentencing Guidelines.7 The district court next applied a
two-level enhancement for obstruction of justice based
5
Although Franklin could recall the details of the April 8
transaction with specificity, he was unable to provide specific
information about the amounts of drugs involved in any of his
prior transactions with Mr. Bryant or the dates on which
those transactions took place. Nor could he estimate the num-
ber of times he had purchased drugs from Mr. Bryant.
6
The Government presented no new evidence at the sen-
tencing hearing.
7
Although the November 2007 Amendments were not in
effect at the time Mr. Bryant was sentenced, the district court
agreed, pursuant to Mr. Bryant’s request, to sentence him
under the November 2007 Amendments. The November 2007
Amendments partially ameliorated the sentencing disparity
between crack and powder cocaine.
8 No. 07-3608
on its finding that Mr. Bryant intentionally had made
material misrepresentations to the court during his first
plea withdrawal hearing. It then denied Mr. Bryant’s
motion for a two-level reduction in offense level for
acceptance of responsibility. As a result of these enhance-
ments, the court determined that Mr. Bryant’s offense
level was 32.
Next, the district court assigned a criminal history
category of IV to Mr. Bryant, based, in part, upon a state-
court conviction for cocaine possession. Mr. Bryant
claimed, however, that the conviction should not be
considered for the purpose of determining his criminal
history category; instead, he submitted, the conviction
should be considered relevant conduct for sentencing
purposes because the conviction involved similar
conduct that had taken place during the time period of
the conspiracy. The district court declined to deem the
conviction relevant conduct.
The district court sentenced Mr. Bryant to 180 months’
imprisonment, a sentence in the middle of the advisory
guideline range for an individual of Mr. Bryant’s criminal
history category and offense level. Because Mr. Bryant
was sentenced before the Supreme Court’s decision in
Kimbrough v. United States, ___ U.S. ___, 128 S. Ct. 558(2007), the district court did not take the sentencing
disparity between crack and powder cocaine into
account when determining Mr. Bryant’s sentence.
Mr. Bryant subsequently filed this appeal.
No. 07-3608 9
II
DISCUSSION
Mr. Bryant raises the following arguments: (1) the
district court abused its discretion in denying his second
motion to withdraw his plea; (2) the district court clearly
erred in finding that the Government had proven, by a
preponderance of the evidence, that the charged con-
spiracy involved crack cocaine; (3) the district court
clearly erred in applying a two-level enhancement for
obstruction of justice based on the statements he made
at his first plea withdrawal hearing; (4) the district court
clearly erred in declining to apply a two-level reduction
for acceptance of responsibility; (5) the district court
clearly erred by increasing his criminal history score
because of his state-court conviction for possession of
cocaine base; and (6) his sentence should be vacated
and remanded for resentencing in light of the Supreme
Court’s opinion in Kimbrough, 128 S. Ct. 558. We shall
address each of these arguments in turn.
A.
Mr. Bryant contends that the district court erred in
denying his second motion to withdraw his guilty plea.
We review a district court’s denial of a motion to with-
draw a plea for abuse of discretion. United States v. Silva,
122 F.3d 412, 414-15 (7th Cir. 1997). After a district court
accepts a defendant’s guilty plea and before it imposes
a sentence, the court may permit the defendant to with-
draw his plea provided that he “can show a fair and
10 No. 07-3608
just reason for requesting the withdrawal.” Fed. R.
Crim. P. 11(d)(2)(B); accord United States v. Underwood, 174
F.3d 850, 852 (7th Cir. 1999). The defendant bears the
burden of proving that a fair and just reason for with-
drawal exists. United States v. Coonce, 961 F.2d 1268, 1275
(7th Cir. 1992).
Mr. Bryant claims that, immediately prior to his bench
trial, he discovered new evidence that undermined the
Government’s case against him: He learned that the
second DEA chemist had mishandled drug samples
during the time period in which he evaluated the sub-
stance at issue in Mr. Bryant’s case, and that the Gov-
ernment no longer intended to introduce the second
chemist’s report or the substance itself into evidence.
Mr. Bryant contends that because he discovered new,
relevant evidence after entering his plea, see, e.g., United
States v. Garcia, 401 F.3d 1008, 1011 (9th Cir. 2005), and
because the discovery of that evidence enabled him to
make a legal argument that he was unaware of at the time
of his plea, see, e.g., United States v. Groll, 992 F.2d 755, 759-
60 (7th Cir. 1993), he has demonstrated a fair and just
reason to withdraw his plea.
We cannot say that the district court abused its discre-
tion in denying this motion. Unlike the defendant in
Garcia, Mr. Bryant did not present newly discovered
evidence relating to his factual guilt or innocence. Garcia,
401 F.3d at 1011-12 (concluding that the defendant’s
discovery of a new witness created a fair and just reason
for withdrawal of the defendant’s guilty plea because the
witness’ statement “raise[d] new questions about [the
No. 07-3608 11
defendant’s] involvement in the illegal activity”). Addi-
tionally, unlike the defendant in Groll, Mr. Bryant did not
introduce evidence that, at the time of his plea, he was
unaware of a legal defense to the crime charged. Groll, 992
F.2d at 758, 759-60 (stating that “being legally innocent of
the crime is a fair and just reason to withdraw a guilty
plea” and concluding that the district court abused its
discretion in denying the defendant’s motion to with-
draw her guilty plea when unrebutted evidence in the
record could have supported her entrapment defense
and the defendant may have been unaware of the en-
trapment defense at the time she pleaded guilty).
The evidence and legal arguments that Mr. Bryant relied
upon in his motion at best relate to the strength of the
Government’s case against him, not his factual or legal
innocence. As we previously have noted, “[a] defendant
is not entitled to withdraw his plea merely because he
has misapprehended the strength of the government’s
case.” Silva, 122 F.3d at 415. When a defendant has been
apprised of the facts giving rise to the charges against
him, the mere fact that he does not know, at the time of
his plea, what evidence the Government will use against
him does not present a “fair and just” reason for him to
withdraw his plea. See Underwood, 174 F.3d at 853-54(concluding that “[the defendant’s] reevaluation of his
trial prospects afforded no basis for withdrawing his
validly-entered guilty pleas”); United States v. Seybold, 979
F.2d 582, 587 (7th Cir. 1992) (noting that Rule 11 “does not
require the trial judge at the plea hearing to air all of the
government’s evidence”). Furthermore, it is far from
clear that Mr. Bryant’s discovery of the problem with one
12 No. 07-3608
of the Government’s chemists would have impacted his
decision to plead guilty. Although Mr. Bryant pleaded
guilty to the charged conspiracy, he specifically reserved
for a bench trial the issues of the type and quantity of
drugs involved in the conspiracy. In other words, he
admitted to conspiring to possess and distribute drugs;
he did not admit that the drugs he conspired to distrib-
ute included cocaine or cocaine base. The discovery of
the chemist’s mishandling of the evidence, however,
relates solely to the issue of the type of drugs involved in
the conspiracy, and is irrelevant to the question of whether
Mr. Bryant conspired to distribute any controlled sub-
stance. As the district court noted, Mr. Bryant “necessarily
challenged [the second chemist’s] finding by saying he
wasn’t going to agree that [the substance] was crack.”
R.183-9 at 17. We therefore cannot say that the district
court abused its discretion in rejecting Mr. Bryant’s
motion to withdraw his plea.
B.
1.
Mr. Bryant raises a number of challenges to the sen-
tence imposed by the district court. Among his other
arguments, Mr. Bryant contends, and the Government
concedes, that his sentence should be vacated and re-
manded in light of the Supreme Court’s decision in
Kimbrough v. United States, ___ U.S. ___, 128 S. Ct. 558(2007). We agree with the parties that Mr. Bryant
preserved this issue. During the sentencing hearing,
which was held before the Supreme Court’s decision in
No. 07-3608 13
Kimbrough, Mr. Bryant maintained that the drugs involved
in the conspiracy were not crack cocaine. As we held in
United States v. Padilla, 520 F.3d 766, 774 (7th Cir. 2008),
such a position is sufficient to preserve the Kimbrough
issue. Accordingly, we vacate Mr. Bryant’s sentence and
remand for resentencing so that the district court may
take into account the sentencing disparity between crack
and powder cocaine when sentencing Mr. Bryant. We
now turn to the remainder of Mr. Bryant’s challenges to
his sentence.
2.
Mr. Bryant challenges the district court’s conclusion
that the charged conspiracy involved crack cocaine. We
review the district court’s finding for clear error, United
States v. Wilson, 437 F.3d 616, 621 (7th Cir. 2006), and shall
reverse its decision “only if we are left with the definite
and firm conviction that a mistake was made.” Padilla,
520 F.3d at 769.
The Government was required to prove, by a prepon-
derance of the evidence, that the charged conspiracy
involved “crack” cocaine. United States v. Johnson, 200
F.3d 529, 537 (2000). Mr. Bryant claims that the Govern-
ment’s evidence on this issue, which consisted solely of
the evidence presented at the bench trial, was insufficient
to support the district court’s finding. In particular,
Mr. Bryant claims that Franklin’s testimony was unreli-
able because, with the exception of the April 8 transaction,
Franklin was unable to recall the details of any of the
transactions in which he allegedly received crack cocaine
14 No. 07-3608
from Mr. Bryant. Mr. Bryant describes Franklin’s testi-
mony as an allegation “that, at some point in the past,
though he doesn’t remember exactly when, [Franklin]
received some amount of crack cocaine [from Mr. Bryant],
though he doesn’t remember how much,” and asserts
that this vague testimony cannot support a finding that
Mr. Bryant conspired to distribute more than fifty grams
of crack cocaine. Appellant’s Br. 28.
Although Franklin’s testimony lacked specific details
about the transactions in which he had obtained crack
cocaine, it nevertheless contained sufficient details to
support the district court’s conclusion. Franklin was not
able to recall the dates on which he received crack cocaine
from Mr. Bryant or the specific quantities of crack cocaine
he received. However, he did testify that each of the
transactions involved more than sixty-three grams of
crack cocaine. In addition, he provided detailed testi-
mony about an occasion when he watched Mr. Bryant
“cook” powder cocaine into crack cocaine. Further-
more, Franklin’s testimony was not the only evidence
presented to the district court on this issue; the Govern-
ment introduced recorded conversations between
Franklin and the informant, in which those two
individuals discussed having Franklin’s supplier “cook”
the cocaine. It also introduced evidence that the sub-
stance that Franklin received on April 8 contained cocaine
base. The district court was entitled to rely on this evi-
dence, in its totality, in determining that the conspiracy
involved crack cocaine. See, e.g., Padilla, 520 F.3d at 770-71(noting that “the government can prove a substance is
crack by offering testimony from people familiar with the
No. 07-3608 15
drug, United States v. Anderson, 450 F.3d 294, 301 (7th Cir.
2006), including . . . an informant’s belief that he was
purchasing crack”); United States v. Earnest, 185 F.3d 808,
813 (7th Cir. 1999) (recognizing that a court may rely on
the testimony of experts and other witnesses in con-
cluding that a substance is crack cocaine).
Mr. Bryant also suggests that, because the Government
could not show that the substance contained sodium
bicarbonate, it failed to prove, by a preponderance of the
evidence, that the substance was crack cocaine. The
Sentencing Guidelines distinguish between “cocaine base”
and “cocaine” for sentencing purposes. U.S.S.G. § 2D1.1(c)
(“Drug Quantity Table”). Although “greater punishment
applies to cocaine base than to cocaine,” Lemon v. United
States, 335 F.3d 1095, 1095 (8th Cir. 2003), the Sentencing
Guidelines did not define “cocaine base” until the Guide-
lines were amended in 1993. United States v. Waters, 313
F.3d 151, 155 (3d Cir. 2002). “Prior to 1993, circuit courts
were divided over whether ‘cocaine base’ under § 2D1.1
included only ‘crack,’ or whether it also broadly encom-
passed all other substances the scientific community
generally considered to be cocaine base.” United States v.
Abdul, 122 F.3d 477, 478 (7th Cir. 1997) (citations omitted)
(discussing the conflicting definitions of cocaine base
adopted by various courts). To resolve the conflict, the
Sentencing Commission proposed an amendment to
Section 2D1.1(c). Id. The amendment, which became
effective in 1993, id. at 479, reads as follows:
“Cocaine base,” for the purposes of [the Sentencing
Guidelines], means “crack.” “Crack” is the street name
16 No. 07-3608
for a form of cocaine base, usually prepared by pro-
cessing cocaine hydrochloride and sodium bicarbonate,
and usually appearing in a lumpy, rocklike form.
U.S.S.G. § 2D1.1(c) note (D) (hereinafter “Note D”).8
Although “the definition of ‘cocaine base’ in the Guide-
lines makes it clear that only the ‘crack’ form of cocaine
base should receive the . . . sentencing enhancement
under § 2D1.1,” United States v. Jones, 159 F.3d 969, 982
(6th Cir. 1998), the Guidelines do not explicitly define
“crack” in terms of its chemical composition, method of
manufacture or physical appearance. See Waters, 313
F.3d at 156 (noting that “there is no precise chemical
definition of crack cocaine,” and concluding that “crack
generally refers more to the way the drug is prepared
and used than the specific chemical composition”).
Perhaps due to the reference to sodium bicarbonate in
Note D and the absence of a specific definition of “crack,”
it has become common for individuals sentenced under
Section 2D1.1 to challenge whether a substance is, in
fact, crack cocaine. Often, as in the case before this
court, these challenges take the form of claims that the
substance at issue cannot be crack cocaine because it
does not contain sodium bicarbonate. See, e.g., Abdul, 122
F.3d at 478. We have rejected this argument. We have
8
“Notes or commentary to the sentencing guidelines are
considered binding authority unless either violative of the
Constitution or a federal statute, or clearly inconsistent with
the guideline[s].” United States v. Brooks, 161 F.3d 1240, 1248
(10th Cir. 1998) (internal quotation marks and citations omitted).
No. 07-3608 17
held that, based on the use of the qualifying term “usu-
ally” in Note D, “crack” is not limited to cocaine that has
been processed with sodium bicarbonate. See id. at 479
(“If courts were to disregard the qualifying term ‘usually,’
crack dealers could avoid the penalties for distribution
of crack by merely finding some substitute for baking
soda in production, or by crushing the rocks so that
the final product resembles powder.”). Other courts
have reached similar conclusions. See United States v.
Whitehead, 487 F.3d 1068, 1072 (8th Cir. 2007) (“[T]he
government need not show the presence of sodium bicar-
bonate in order to prove that cocaine is crack. . . .”);
United States v. Eli, 379 F.3d 1016, 1022 (D.C. Cir. 2004)
(“The Sentencing Guidelines do not insist that crack can
be made only with sodium bicarbonate; they merely
state that it is ‘usually prepared’ that way.” (internal
citation omitted)); Waters, 313 F.3d at 155 (“[I]t is not
necessary for the government to show that a substance
contains sodium bicarbonate in order to demonstrate by
a preponderance of the evidence that the drugs in ques-
tion are crack cocaine.”); United States v. Brooks, 161 F.3d
1240, 1248 (10th Cir. 1998) (“We interpret the qualifier
‘usually’ . . . as an acknowledgment that other methods
of crack preparation exist and that not all forms of
‘cocaine base’ need contain sodium bicarbonate to
qualify as crack for sentencing purposes. Indeed, it
appears that the method which uses sodium bicarbonate
is the least sophisticated and yields the lowest purity.”
(internal quotation marks and citations omitted)); Jones,
159 F.3d at 983 (“[T]he presence of sodium bicarbonate
is not a necessary prerequisite to a district court’s
factual determination that cocaine base is crack.”).
18 No. 07-3608
Our approach takes into account the fact that there are
multiple methods of manufacturing crack cocaine. Indeed,
we have stated expressly that “while crack might gen-
erally be produced using sodium bicarbonate, production
with sodium bicarbonate is not the exclusive preparation
method recognized for the purposes of § 2D1.1(c).” Abdul,
122 F.3d at 479. Two of our sister circuits have
recognized that chemical compounds other than sodium
bicarbonate, including sodium borate and niacinamide,
may be used to convert powder cocaine into crack cocaine.9
Furthermore, at least one expert has opined that, even
where sodium bicarbonate is utilized to process powder
cocaine into crack, the final product may not necessarily
contain detectable quantities of sodium bicarbonate.
Waters, 313 F.3d at 153 (referring to the statements of a
DEA chemist who testified as follows: “If the conversion
9
United States v. Eli, 379 F.3d 1016, 1022 (D.C. Cir. 2004)
(holding that the district court did not clearly err in
“conclud[ing] that the presence of sodium borate did not
undermine the conclusion that the substance was crack,” based,
in part, on an expert’s testimony that he: (1) had converted
powder cocaine to crack using sodium borate; (2) had previously
detected sodium borate in other crack samples; and (3) was
aware that other chemists had detected sodium borate in
crack samples); United States v. Waters, 313 F.3d 151, 156-57
(3d Cir. 2002) (noting an officer’s testimony that “niacinamide
is commonly used in the Philadelphia area as a substitute
for sodium bicarbonate,” and concluding that the district court
did not err in finding that the substance at issue was crack
cocaine).
No. 07-3608 19
is performed properly and you use the correct amounts
of sodium bicarbonate and powdered cocaine . . . you
should have no sodium bicarbonate left when the con-
version is complete. However, traditionally, what we
find is that out on the street an excess of this bicarbonate
is used in the conversion.” (internal quotation marks and
citations omitted)).
Cases from this and other circuits establish, therefore,
that the presence of sodium bicarbonate is not a litmus test
for establishing that a substance is “crack” for the pur-
poses of Section 2D1.1. Instead, courts have considered
the following factors, among others, in determining
whether a substance qualifies as crack for sentencing
purposes: (1) whether “the substance at issue [has] tested
positive for the presence of cocaine base”;1 0 (2) the color
of the substance;11 (3) the shape and texture of the sub-
stance;12 (4) the method of packaging;1 3 (5) the price of the
10
United States v. Brown, 499 F.3d 817, 824 (8th Cir. 2007); see
also Brooks, 161 F.3d at 1247, 1248-49; United States v. Canales,
91 F.3d 363, 368 (2d Cir. 1996) (concluding that the Guidelines
were not ambiguous as applied to the defendant because,
among other things, DEA reports indicated that the substance
tested positive for the presence of cocaine base).
11
United States v. Morris, 498 F.3d 634, 644 (7th Cir. 2007)
(“yellowish-white” substance); Canales, 91 F.3d at 368 (white
substance).
12
Morris, 498 F.3d at 644 (noting that “[o]ther evidence corrobo-
rated the fact that the drugs in question were crack cocaine,” in-
cluding a DEA agent’s testimony that “ ‘the material . . . was
(continued...)
20 No. 07-3608
substance; and (6) whether the seller represents the
substance as or understands the substance to be crack.1 4
Indeed, a comprehensive analysis that focuses on not
only the chemical composition of a substance but also its
appearance and other properties, its packaging, and the
representations associated with its sale is consistent
with the congressional concerns that prompted the statu-
tory sentencing disparity: crack’s low cost, high availabil-
12
(...continued)
kind of wet, which is not uncommon for crack’ ”); Brown,
499 F.3d at 824 (“rock” form); Canales, 91 F.3d at 368 (“chunky”
substance).
13
Morris, 498 F.3d at 644 (noting that testimony “describ[ing] the
usual method for packaging crack” and indicating that the
“drugs that were recovered were ‘packaged for distribution’ as
crack cocaine” supported the district court’s conclusion that “the
drugs in question were crack cocaine and not some other
form of cocaine base”).
14
Eli, 379 F.3d at 1021 n.7 (declining to decide whether the
Government must prove that the substance would pass for
crack on the streets, but concluding that, if such a require-
ment did exist, the requirement would be satisfied by the
defendant’s admission that the substance was crack and “by the
fact that [the defendant] sold the drugs as ‘crack’ to an under-
cover officer”); Canales, 91 F.3d at 368 (“The street name ‘crack’
is not ambiguous, because crack has a common and ordinary
meaning that is understood by [the defendant] . . . by others
in the drug trade, and by citizens in communities that are
plagued by the drug.”).
No. 07-3608 21
ity and quick, intense high.1 5 See also United States v. Scott,
No. 08-2579, slip op. at 10 (7th Cir. Feb. 11, 2009) (“There
are special dangers posed to society when cocaine is
marketed in a form that makes it more readily available
to a wider and more vulnerable part of our population.”).
Crack is not defined merely by its secondary ingredients;
it is a “product,” particularly dangerous because of its
ability to reach a wide, susceptible market and produce,
in that market, disastrous effects for both those who
fall prey to its addictive allure and the people who come
in contact with them.
Considering the concerns that gave rise to the sen-
tencing disparity, we conclude that district courts may
15
Although there is little legislative history discussing the
reasoning behind the sentencing disparity between crack and
powder cocaine, Congress’ concern for the impact that crack
would have on individuals and communities is clear. See, e.g.,
132 Cong. Rec. 26,447 (1986) (statement of Sen. Chiles) (“The
whole Nation now knows about crack cocaine. They know it
can be [bought] for the price of a cassette tape, and make
people into slaves.”); 132 Cong. Rec. 19,241 (1986) (statement of
Sen. Chiles) (“Crack is available to the young, and it will be in
the schools this fall. . . . We have all heard of cocaine, but I must
stress to you that crack cocaine is something altogether dif-
ferent. It is more powerful; it is cheaper to use; it is also far
more addictive. Crack cocaine is a purified form of powdered
cocaine that is smoked. A hit of crack costs around $10, well
within the budget of any teenager. When smoked, crack reaches
the brain in less than 10 seconds. It produces a short but
incredibly powerful high that is followed by an equally power-
ful low.”).
22 No. 07-3608
rely on a number of factors, including those we have
discussed, in determining whether a substance is crack. We
restate our earlier conclusion that the Government need
not prove that a substance contains sodium bicarbonate
in order to establish, for the purposes of Section 2D1.1, that
a substance is crack. Accordingly, we cannot say that
the district court clearly erred in determining that
Mr. Bryant conspired to distribute more than fifty grams
of crack cocaine.
3.
The district court concluded that Mr. Bryant made
material misrepresentations during his first plea with-
drawal hearing, in which he claimed that he was pres-
sured into pleading guilty and that his former attorney
told him that he was unprepared for trial. Therefore, the
district court imposed a two-level enhancement for ob-
struction of justice under Section 3C1.1 of the Sentencing
Guidelines. U.S.S.G. § 3C1.1. We review for clear error
the district court’s factual finding underlying the decision
to impose the enhancement. United States v. Griffin,
310 F.3d 1017, 1022 (7th Cir. 2002).
An obstruction of justice enhancement may be imposed
when a defendant has “willfully obstructed or impeded, or
attempted to obstruct or impede, the administration of
justice with respect to the investigation, prosecution, or
sentencing of the instant offense of conviction.” U.S.S.G.
§ 3C1.1. The obstructive conduct must be related to the
“offense of conviction and any relevant conduct” or a
“closely related offense.” Id. “Committing, suborning, or
No. 07-3608 23
attempting to suborn perjury supports an obstruction
enhancement.” Griffin, 310 F.3d at 1023 (citing U.S.S.G.
§ 3C1.1 cmt. n.4(b)). “In order to find obstruction based
on perjury, the sentencing court must find that the defen-
dant willfully made misrepresentations under oath that
were relevant to the prosecution, and specifically in-
tended to obstruct justice.” United States v. Carroll, 412
F.3d 787, 793 (7th Cir. 2005) (citing United States v.
Dunnigan, 507 U.S. 87, 94 (1993)).
Mr. Bryant claims that the Government failed to demon-
strate that he made false representations with the intent
to obstruct justice. Although he admits that the state-
ments he made at the plea withdrawal hearing conflicted
with his former attorney’s testimony, he claims that the
statements were an honest, though perhaps inaccurate,
recollection of his discussions with his attorney. He
asserts that his statements were not the result of a specific
intent to obstruct justice, but, rather, were the product
of his own misunderstanding and faulty memory.
The district court explicitly addressed the willfulness of
Mr. Bryant’s statements. It rejected his claim that he
lacked specific intent to mislead the court:
It wasn’t that . . . [Mr. Bryant] perceived that [his
attorney] wasn’t prepared. The statements under oath
were that Mr. Willis told him he had to plead
guilty. . . . [T]here was nothing there about perception.
It was actual statements.
R.183-11 at 3. The district court concluded, based on its
observation of Mr. Bryant and his former attorney—the
24 No. 07-3608
only witnesses to testify at the plea withdrawal hear-
ing—that Mr. Bryant “lied in his testimony.” R.183-8 at 12.
The district court was entitled to make this conclusion. The
district court simply based its determination that
Mr. Bryant had perjured himself on its evaluation of the
sworn statements of Mr. Bryant and his former attorney.
We cannot say that the court clearly erred in reaching
its conclusion.
4.
The district court also determined that Mr. Bryant was
not entitled to a two-level reduction for acceptance of
responsibility. The Guidelines permit district courts to
apply a two-level reduction when a defendant “clearly
demonstrates acceptance of responsibility for his offense.”
U.S.S.G. § 3E1.1(a). The district court concluded, based
on Mr. Bryant’s statements at his first plea withdrawal
hearing, that Mr. Bryant was not entitled to the two-
level reduction.
The Government submits that the district court’s con-
clusion was correct; it notes that conduct resulting in an
obstruction of justice enhancement “ordinarily indicates
that the defendant has not accepted responsibility for his
criminal conduct.” U.S.S.G. § 3E1.1 cmt. n.4.1 6 In the Gov-
16
Accord United States v. Martinez, 169 F.3d 1049, 1056 (7th Cir.
1999) (“Where a defendant falsely denies [ ] relevant conduct
that the court determines to be true, he has acted in a manner
(continued...)
No. 07-3608 25
ernment’s view, this is not the type of extraordinary case
where both an obstruction of justice enhancement and
an acceptance of responsibility reduction are warranted.
On the basis of this record, the district court reasonably
could have determined that Mr. Bryant had not accepted
responsibility for his conduct. Nevertheless, a statement
made by the district court in the course of its proceedings
gives us pause: The district court indicated that, because
of Mr. Bryant’s statements at his first plea withdrawal
hearing, “there was obstruction, and, you know, it was [a]
very foolish thing to do because legally that means
there’s no acceptance of responsibility.” R.183-8 at 13.
However, the district court later recognized that “there
are exceptions where somebody may have obstructed
justice and could be allowed to accept responsibility.”
R.183-11 at 6.
It is clear that, while a finding that a defendant ob-
structed justice “ordinarily indicates that the defendant
has not accepted responsibility for his criminal conduct,”
U.S.S.G. § 3E1.1 cmt. n.4 (emphasis added), the ap-
plication of an obstruction of justice enhancement does not
necessitate the denial of a reduction in offense level for
acceptance of responsibility. See, e.g., United States v. Davis,
442 F.3d 1003, 1009-10 (7th Cir. 2006) (“A defendant
whose sentence was properly enhanced for obstruction
16
(...continued)
inconsistent with the acceptance of responsibility, and the
district court may refuse to grant this reduction.” (internal
citations and quotation marks omitted)).
26 No. 07-3608
of justice is presumed not to have accepted responsibil-
ity. . . . It is only under exceptional circumstances that a
defendant who has received a sentence enhancement for
obstruction of justice will be given a downward adjust-
ment for acceptance [of] responsibility.” (internal citations
omitted)). Because we remand Mr. Bryant’s sentence on
other grounds, we need not determine whether the
district court clearly erred in denying Mr. Bryant an
acceptance of responsibility adjustment. The district
court will have the opportunity to revisit this issue on
remand.
5.
The parties agree that, during the relevant time period,
Mr. Bryant pleaded guilty in Illinois state court to simple
possession of less than fifteen grams of cocaine. At his
sentencing hearing, Mr. Bryant argued that the state-
court conviction should not be considered when calculat-
ing his criminal history category; instead, he maintained
that it should be considered as relevant conduct for
sentencing purposes, because the conduct giving rise to
the conviction involved possession of distribution-level
quantities of cocaine during the conspiratorial time
period. In the district court, the Government disagreed
with Mr. Bryant’s contention: It asserted that the state-
court conviction should not be considered relevant
conduct because Mr. Bryant pleaded guilty to mere
possession of, and not distribution of, cocaine. The Gov-
ernment also claimed that there was insufficient evidence
for the court to find that the conduct underlying the
No. 07-3608 27
conviction was related to the charged conspiracy. In its
argument, the Government suggested that the court
could not use the information in the police reports and
charging documents to determine whether the state-
court conviction should be considered relevant conduct.
R.183-11 at 10. On appeal, however, the Government now
concedes that “the district court could have found that
the . . . state case constituted relevant conduct.” Govern-
ment’s Br. 35.
The district court rejected Mr. Bryant’s claim that the
conviction should be considered relevant conduct, con-
cluding that it “[did not] have enough information to
say that [the conviction was] part of th[e] conspiracy.”
R.183-11 at 15. Consequently, the court assigned Mr.
Bryant a criminal history level of IV.1 7
When calculating a defendant’s criminal history cate-
gory, a district court may not consider prior convictions
for acts which constitute relevant conduct—conduct that
was part of the instant offense. U.S.S.G. § 4A1.2 cmt. n.1.
Whether a prior conviction may be considered relevant
conduct depends on the acts which gave rise to the con-
viction; as we have noted, the name of the offense to which
a defendant pleaded guilty “cannot be the basis of the
district court’s [relevant conduct] determination, for . . .
the sentencing guidelines direct courts to look to the
underlying conduct of the offense, and not the name of
17
The parties agree that, had the conviction been considered
relevant conduct, Mr. Bryant would have been assigned a
criminal history category of III.
28 No. 07-3608
the offense itself, when assessing relevant conduct.”
United States v. Olson, 408 F.3d 366, 374 (7th Cir. 2005)
(instructing the district court to determine whether the
defendant “possessed the drugs [involved in his plea to
possession of a controlled substance] merely for his
personal use, or with an intent to distribute”) (citing
United States v. Garecht, 183 F.3d 671, 674 (7th Cir. 1999) and
United States v. Wyss, 147 F.3d 631, 632 (7th Cir. 1998)). See
U.S.S.G. §§ 4A1.2, 4A1.2 cmt. n.1 (noting that, for the
purpose of computing the defendant’s criminal history
level, a “prior sentence [is] any sentence . . . for conduct not
part of the instant offense,” as specified in Section 1B1.3
(emphasis added)); U.S.S.G. § 1B1.3(a)(2) (stating that
relevant conduct includes “all acts and omissions . . . that
were part of the same course of conduct or common
scheme or plan as the offense of conviction” (emphasis
added)). Therefore, the district court must consider the
acts giving rise to Mr. Bryant’s state-court conviction and
evaluate whether those acts and the charged conspiracy
were either “part of a single episode, spree, or ongoing
series of offenses,” or “substantially connected to each
other by . . . [a] common factor, such as common victims,
common accomplices, common purpose, or similar
modus operandi.” U.S.S.G. § 1B1.3 cmt. n.9. Where the
conduct underlying a prior conviction is unclear, the
district court must “make specific factual findings re-
garding the underlying conduct . . . thereby clearly pro-
viding the basis for its ultimate resolution of the
relevant conduct question.” Olson, 408 F.3d at 374.
We cannot tell, based on the record before us, whether
the district court ultimately concluded that it could not
No. 07-3608 29
consider the underlying police reports and charging
documents in its relevant-conduct analysis. Certain
statements indicate that the district court believed that
it could consider only the conduct to which Mr. Bryant
ultimately pleaded guilty in its relevant-conduct analysis.1 8
Other statements, however, indicate that the district
court simply did not have enough information to deter-
mine whether the conduct underlying the conviction
was relevant to the charged conspiracy.1 9 On remand, the
district court will have the opportunity to further explain
its reasoning and to conduct any fact-finding necessary
to resolve this issue.
Conclusion
In sum, we hold that the evidence of the DEA chemist’s
mishandling of evidence related solely to the strength of
the Government’s case and did not present a fair and
just reason for Mr. Bryant to withdraw his guilty plea.
Therefore, the district court did not abuse its discretion
in rejecting Mr. Bryant’s motion to withdraw his guilty
plea. Furthermore, we conclude that the district court
appropriately addressed the issues of whether the
18
See, e.g., R.183-11 at 14-15 (“I think if the government tried
to say this was delivery of a controlled substance, you would
be well within your rights to come back and say, ‘Wait a
minute. He pled guilty to possession, and that’s all you can
do,’ so if it made a difference.”).
19
See, e.g., R.183-11 at 15 (“I don’t have enough information to
say that it is part of this conspiracy. . . .”).
30 No. 07-3608
charged conspiracy involved crack cocaine and whether
an obstruction of justice enhancement was appropriate.
Nevertheless, we vacate Mr. Bryant’s sentence and remand
for resentencing so that the district court may take into
account the sentencing disparity between crack and
powder cocaine when sentencing Mr. Bryant. On
remand, the district court will also have the opportunity to
address fully whether Mr. Bryant is entitled to an accep-
tance of responsibility adjustment and whether Mr.
Bryant’s state-court conviction for possession of cocaine
constitutes relevant conduct for sentencing purposes.
Therefore, Mr. Bryant’s conviction is affirmed, but his
sentence is vacated and his case is remanded to the
district court for resentencing.
A FFIRMED in part, V ACATED
and R EMANDED in part
2-26-09