United States Court of Appeals

For the First Circuit

No. 08-1160

UNITED STATES OF AMERICA,

Appellee,

v.

CHRIS BRYANT,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Nathaniel M. Gorton, U.S. District Judge]

Before

Torruella, Stahl, and Howard,

Circuit Judges.

William W. Fick, Federal Defender Office, for appellant.

Randall E. Kromm, Assistant United States Attorney, with whom

Michael J. Sullivan, United States Attorney, was on brief for

appellee.

July 8, 2009
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TORRUELLA, Circuit Judge. On September 14, 2007,

defendant Chris Bryant pleaded guilty to a one-count indictment

charging him with distribution of cocaine base, in violation of 21

U.S.C. § 841(a)(1). At a sentencing hearing on December 19, 2007,

the district court sentenced Bryant to ninety-months imprisonment,

based in part on its determination that he qualified as a career

offender under U.S.S.G. § 4B1.1. The court also imposed a fiveyear term of supervised release. In this appeal, Bryant challenges

the district court's career offender designation and the district

court's determination that an earlier uncharged transaction

involving Bryant constituted relevant conduct under U.S.S.G.

§ 1B1.3. After careful consideration, we affirm in part, reverse

in part, and remand for further proceedings.

I. Background

As this appeal follows Bryant's guilty plea, we draw the

facts from the presentencing report ("PSR") and the transcript of

the sentencing hearing. See United States v. Jaca-Nazario, 521

F.3d 50, 52 (1st Cir. 2008).

In the summer and fall of 2006, Bryant participated in

two sales of crack cocaine to an undercover officer in Mattapan,

Massachusetts. The first occurred on August 2, 2006, and the

second occurred on November 15, 2006. Bryant was not charged with

the August 2, 2006 transaction.
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On August 2, 2006, at about 1:15 p.m., an undercover

officer drove into an area near 17 Gleason Street, looking for an

individual from whom he had previously purchased crack cocaine. He

passed four black males sitting on the curb. One of the four men

called out to the officer and asked him what he was looking for.

The officer responded that he was inquiring about his prior

contact, providing a description of the individual. One of the

males then said that the person whom the officer had described was

not around and again asked the officer what he was looking for.

The officer replied that he wanted $150 worth of "flav," a

reference to cocaine. One of the males offered instead to sell

marijuana to the officer, but the officer declined the offer. Upon

hearing his response, that same male began making calls to locate

crack cocaine that the officer could then purchase. At this time,

another male, later identified as Bryant, asked the officer if he

was a cop. The officer said no and showed Bryant his cellular

telephone, which contained the target individual's phone number.

Bryant and another male at the scene, Kyle Alston, then told the

officer to meet them at another location, the corner of Gleason and

Bradshaw streets.

The officer met Bryant and Alston at the designated

corner, and then walked with them to another nearby corner. Alston

asked the officer for money, indicating that he would be using it

to buy the drugs. Bryant told the officer that it was "ok" and
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that he should try the "product" because it was "high-quality."

Bryant also stated that the "product" was his and that he smoked

marijuana, but was selling cocaine to make some money. Alston

returned and handed the officer a plastic bag containing four rocks

of what was later determined to be 0.7 grams of crack cocaine.

Bryant told the officer that he should hide the drugs in his anal

cavity because the police were in the area. The officer exchanged

phone numbers with Bryant.

After the sale to the officer was completed, Bryant and

Alston were stopped by other police officers. Soon thereafter,

Bryant and Alston saw the undercover officer again and told him to

be careful because police were in the area.

The second transaction occurred over three months later,

on November 15, 2006. The same undercover officer was driving on

Bradshaw Street when he saw Bryant. The officer asked Bryant if he

recognized him. Bryant indicated that he did and asked the officer

what he wanted. The officer told Bryant that he wanted the same

thing as last time. Bryant said he would take care of him and then

entered the officer's car and asked him to drive around the block.

Bryant called multiple people in an attempt to locate drugs for the

officer. Bryant then directed the officer to Baker Avenue, and

asked him to park the car. Bryant requested money from the

officer. After some hesitation, the officer gave Bryant money.

Bryant exited the car and entered 18 Baker Avenue. He returned to
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the car shortly thereafter. The officer subsequently drove Bryant

back to Gleason Street, where, upon the officer's request, Bryant

dropped a plastic bag containing six rocks of what was later

determined to be 0.74 grams of crack cocaine into the cupholder of

the officer's car.

On January 10, 2007, federal authorities arrested Bryant

pursuant to a complaint alleging distribution of cocaine base.

Bryant's one-count indictment, handed down on February 28, 2007,

charged him with knowingly and intentionally distributing a

quantity of cocaine base on November 15, 2006, in violation of 21

U.S.C. § 841(a)(1) as well as with a related forfeiture allegation

under 21 U.S.C. § 853. The indictment did not reference the

August 2, 2006 transaction. Bryant entered a plea of guilty on

September 14, 2007. On November 9, 2007, the Probation Office

issued an initial PSR.

As originally issued, the PSR stated that Bryant was

responsible for both the 0.74 grams of crack cocaine the undercover

officer purchased in the November 15, 2006 transaction and for the

0.70 grams of crack cocaine the undercover officer purchased in the

August 2, 2006 uncharged transaction. Based on this total of 1.44

grams of crack cocaine, the PSR calculated Bryant's base offense

level ("BOL") to be 16. The PSR reduced the BOL by three levels

for acceptance of responsibility, bringing the total offense level

to 13. The PSR applied a criminal history category of II due to
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one countable prior New York conviction for attempted sale of a

controlled substance in 1996 (hereinafter the "New York

conviction"). The PSR calculated a Guideline Sentencing Range

("GSR") of 15–21 months imprisonment. See U.S.S.G. § 5A.

On November 20, 2007, the government objected to the

PSR's calculation of Bryant's criminal history. The government

contended that the PSR omitted a November 1997 conviction from the

Suffolk Superior Court for conspiracy to violate the Massachusetts

controlled substance laws in November 1997 (hereinafter the

"Suffolk Superior Court conviction"). The government argued that

this additional conviction would result in Bryant's designation as

a career offender and a GSR of 151–188 months of imprisonment.

Bryant also objected to the PSR. He objected to the

offense level calculations in the PSR arguing that the uncharged

sale of 0.7 grams of crack cocaine on August 2, 2006 should not be

included as relevant conduct. Bryant contended that the August 2,

2006 and the November 15, 2006 sale were not part of a "common

scheme or plan" nor were they part of the "same course of conduct"

within the meaning of U.S.S.G. § 1B1.3(a)(2). Bryant also objected

to his potential designation as a career offender, alleging that

the Suffolk Superior Court conviction was no longer valid and in

any event could not qualify as a career offender predicate because

the object of a conspiracy to violate the drug laws in

Massachusetts is not necessarily a "controlled substance offense"
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within the meaning of U.S.S.G. § 4B1.2(b). Similarly, Bryant

claimed that in the absence of court records of the type required

by the Supreme Court in Shepard v. United States, 544 U.S. 13

(2005) and Taylor v. United States, 495 U.S. 575 (1990), there was

insufficient evidence to prove the existence of the New York

conviction.

In response to these objections, the Probation Office

issued a revised PSR, dated December 6, 2007, which concluded that

Bryant was a career offender under U.S.S.G. § 4B1.1 and agreed with

the government that the GSR was 151 to 188 months.

The district court held a sentencing hearing on

December 19, 2007. It began by noting the "enormous" disparity

between the offense level attributed to the drug distribution

offense for which Bryant was being sentenced, and the offense level

computation resulting from the application of the career offender

provisions. The district court noted that it was disinclined to

impose a sentence either within the career offender guideline range

or within the lower range calculated in the initial PSR, citing

problems with the evidence used to establish the appropriate

predicate offenses and convictions. However, the district court

also noted that Bryant was a "serious offender" and extenuating

circumstances were present in this case that would lead it to

impose a much higher sentence than that called for by a simple
 The district court noted that 1.44 grams of crack cocaine and 1

criminal history category III yields a GSR of 18 to 24 months.

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application of 1.44 grams of crack cocaine and criminal history

category III.1

After giving Bryant's counsel the opportunity to address

the objections he had made to the PSR, the district court concluded

that it would hold Bryant responsible for the August 2, 2006

transaction. With respect to Bryant's objection to the use of the

Suffolk Superior Court conviction, the district court found that

Bryant pleaded guilty to a conspiracy to traffic in cocaine and

that the conviction constituted a predicate for establishing that

he was a career offender. Finally, with respect to the New York

conviction, the district court found that, based upon the

preponderance of the evidence, there was sufficient evidence to

show that Bryant was convicted for that offense. The district

court, therefore, found that the government offered sufficient

proof to a preponderance of the evidence that established Bryant as

a career offender.

The district court, however, explained that it would not

impose the recommended minimum guideline sentence of 151 months

triggered by the career offender designation because of Bryant's

attempts to rehabilitate himself and the fact that Bryant provided

care for his children. Thus, it imposed a sentence of imprisonment

for a term of ninety months, recommended participation in the
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Bureau of Prisons' 500-hour residential drug abuse program, and

recommended participation in a mental health treatment program.

Finally, the district court ordered that upon Bryant's release, he

be placed in supervised release for a term of five years, the first

six months of which would have to be served at a residential reentry center.

Bryant timely appeals the district court's ruling.

II. Discussion

On appeal, Bryant asserts that the district court erred

by designating him as a career offender. Specifically, Bryant

argues that the government failed to satisfy its burden of proving

the fact of the New York and Suffolk Superior Court convictions,

the two prior convictions upon which the district court relied for

its determination of Bryant's career offender status. In the

alternative, Bryant argues that even if the government had met its

burden, the two prior convictions cannot be classified as predicate

offenses for purposes of career offender status. Further, Bryant

appeals the district court's determination that the uncharged

August 2, 2006 transaction could be deemed relevant conduct for

sentencing purposes.

For the reasons stated below we conclude that the

district court appropriately found the Suffolk Superior Court

conviction to be a predicate offense for career offender purposes

and did not clearly err in finding the August 2, 2006 conviction to
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be relevant conduct. However, we conclude that the district court

committed clear error in finding that the government met its burden

of proving the fact of the New York conviction.

A. Standard of Review

As a general matter, we review a sentencing court's legal

determinations of the Sentencing Guidelines' meaning and scope de

novo and its factual determinations for clear error. United States

v. Hoey, 508 F.3d 687, 690 (1st Cir. 2007). Specifically,

"[w]hether a prior conviction qualifies as a predicate offense

under U.S.S.G. § 4B1.1 is a question of law that we review de

novo." United States v. Almenas, 553 F.3d 27, 31 (1st Cir. 2009);

United States v. Santos, 363 F.3d 19, 22 (1st Cir. 2004). A

sentencing court's factual finding as to whether a prior conviction

exists for career offender purposes is reviewed for clear error,

United States v. Díaz, 519 F.3d 56, 67 (1st Cir. 2008), as is its

determination of whether a particular drug quantity that was part

of prior drug sale should be included as relevant conduct at

sentencing, see United States v. Barbour, 393 F.3d 82, 93 (1st Cir.

2004).

B. Eligibility for Career Offender Status

The Sentencing Guidelines provide that a defendant be

classified as a career offender if he meets the following criteria:

(1) the defendant was at least eighteen years old at the time he or

she committed the offense of conviction; (2) the offense of
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conviction is a felony that is either a crime of violence or a

controlled substance offense; and (3) the defendant has been

previously convicted of two prior felonies of either a crime of

violence or a controlled substance offense. U.S.S.G. § 4B1.1(a);

see also Almenas, 553 F.3d at 31.

1. Proving the Fact of the Conviction for

Purposes of Career Offender Status

The government bears the burden of establishing, by a

preponderance of the evidence, the existence of a prior conviction

for sentencing enhancement purposes. United States v. McKenzie,

539 F.3d 15, 18–19 (1st Cir. 2008). "The Government may satisfy

its burden by producing a certified copy of the conviction or an

equivalent proffer." Id. at 19 (citing Shepard, 544 U.S. at 26,

for the proposition that an equivalent proffer includes official

court documents). "Once the government's threshold burden has been

met, the conviction is presumed valid for purposes of applying the

sentencing guidelines." United States v. Unger, 915 F.2d 759, 761

(1st Cir. 1990).

i. The New York Conviction

The government was unable to provide a judicial record of

the fact of Bryant's New York conviction. The PSR noted that the

New York Supreme Court Clerk's office was unable to locate the file

for the case. To prove the fact of this conviction, the PSR and

the government relied upon the criminal history record maintained

by the National Crime Information Center ("NCIC") and the New York
 We note that although Shepard and Taylor concerned the Armed 2

Career Criminal Act, in United States v. Giggey, 551 F.3d 27, 38

(1st Cir. 2008) (en banc), we held that the categorical approach is

also appropriate in interpreting the career offender guideline.

See Almenas, 553 F.3d at 33 (describing categorical approach and

its application to career offender guideline).

 The sources to which Shepard refers include "the statutory 3

definition, charging document, written plea agreement, transcript

of plea colloquy, and any explicit factual finding by the trial

judge to which the defendant assented." Shepard, 544 U.S. at 16.

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State Police Information Network ("NYSPIN") as well as the

incarceration record from the New York Department of Correctional

Services.

Bryant argues that the government is constrained as to

what it can rely on to prove the fact of a conviction, contending

that the Supreme Court in Shepard required that the existence of a

prior conviction be proved by judicial records.2

We decline the invitation to read Shepard as broadly as

Bryant does. As we have stated previously, "Shepard and its

progenitor, Taylor . . ., address the appropriate sources for

ascertaining the elements of a putative predicate offense when the

statute of conviction encompasses both conduct that would

constitute a predicate offense and conduct that would not."3

United States v. Pelletier, 469 F.3d 194, 202 (1st Cir. 2006).

Specifically, Shepard concerned itself with the sources upon which

a sentencing court can rely to determine the "character" of an

offense. See 544 U.S. at 16. This is a different question than

what we are presented with in the instant case. More precisely, we
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agree with our sister courts that Shepard does not control here

because the Shepard Court "did not address what documents can be

used to prove the fact of a prior conviction." United States v.

Zuniga-Chavez, 464 F.3d 1199, 1204 (10th Cir. 2006) (emphasis in

original); see also United States v. Neri-Hernandes, 504 F.3d 587,

591 (5th Cir. 2007) (ruling that "Shepard does not apply when

determining whether the government has satisfied its burden of

proof as to the existence of a prior conviction"); United States v.

Sanders, 470 F.3d 616, 623-24 (6th Cir. 2006) (noting that Shepard

does not control the inquiry as to whether the government has

provided sufficient evidence to establish a fact of the

conviction).

While Bryant argues that "it would make little sense to

permit courts to consider a broader array of less reliable, less

certain, non-judicial records to determine whether such a

conviction even existed, in the first place," it does not logically

follow that we should extend Shepard's rule governing judicial

records to the instant facts when the concerns that animated the

Supreme Court in Shepard and Taylor are not readily applicable.

There is little danger that a sentencing court's inquiry into the

existence of a prior conviction would engender the same kind of

"practical difficulties and potential unfairness" that could be

present in a determination of whether a defendant's convictions

were violent felonies, which was at issue in Shepard and Taylor.
 An uncontested PSR may be sufficient to provide evidence of a 4

prior conviction where the defendant fails to object to its recital

of prior convictions. Pelletier, 469 F.3d at 202–03. We are not

faced with this situation in Bryant's case because Bryant's counsel

properly objected to the lack of adequate evidence to prove the New

York conviction.

 The requirement that the government demonstrate that contested 5

information in the PSR, including information regarding prior

convictions, be established using a sufficiently reliable source is

consistent with the requirements of the Sentencing Guidelines.

U.S.S.G. § 6A1.3 states that when a court resolves "any dispute

concerning a factor important to the sentencing determination, the

court may consider relevant information without regard to its

admissibility under the rules of evidence . . . , provided that the

information has sufficient indicia of reliability to support its

probable accuracy." U.S.S.G. § 6A1.3(a) (emphasis added); see

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Shepard, 544 U.S. at 20 (quoting Taylor, 495 U.S. at 601).

Establishing the fact of a prior crime is a more discrete inquiry

that is not as susceptible to the lengthy and cumbersome collateral

trials of the kind the Shepard and Taylor Courts hoped to avoid.

Although Shepard does not control here, the district

court must nevertheless determine whether the evidence is

sufficiently reliable. When a defendant objects to the fact of a

conviction as Bryant does here, we have held that: 4

[T]he Government may not simply rely on

assertions in a presentence report if those

assertions are contested by the defendant.

Thus, when the defendant calls into dispute a

presentence report's description of an alleged

prior conviction, the Government must

demonstrate that the description in the report

is based on a sufficiently reliable source to

establish the accuracy of that description.

United States v. Brown, 510 F.3d 57, 75 (1st Cir. 2007) (quoting

United States v. Price, 409 F.3d 436, 444 (D.C. Cir. 2005)). We 5
Zuniga-Chavez, 464 F.3d at 1203 (discussing U.S.S.G. § 6A1.3(a) in

its analysis of whether sources used to prove fact of prior

conviction were sufficiently reliable); see also United States v.

Marceau, 554 F.3d 24, 31 (1st Cir. 2009) (noting the rule in

U.S.S.G. § 6A1.3(a) and stating that the district court has broad

discretion to determine the reliability of particular evidence).

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conclude that the district court, by failing to heed this language

from Brown, committed clear error.

Here, to prove the fact of this conviction, the PSR and

the government relied upon the criminal history record maintained

by the NCIC, the NYSPIN, and the incarceration record from the New

York Department of Correctional Services. Responding to Bryant's

objections to this evidence, the district court stated that "based

upon the preponderance of the evidence standard . . . there is

sufficient evidence to demonstrate that this defendant was, in

fact, convicted in the so-called New York conviction of a crime

that forms a predicate to his being considered to be a career

offender." The district court added: "I do acknowledge that there

are some close questions that had to be determined in making this

finding, but the Court does find that the government has

sufficiently offered proof to a preponderance of the evidence that

both of these crimes were committed and the defendant was convicted

of them and, together, they establish that he is, by virtue of this

third conviction that he's about to be sentenced for, a career

offender."
 We leave it to the district court to decide how best to 6

determine the reliability of the sources the government used to

prove the fact of the New York conviction. In addition, we note

that while some courts have approved the use of NCIC reports to

establish a prior conviction for sentencing purposes, other courts

have noted mistakes in these reports. Compare United States v.

Kattaria, 553 F.3d 1171, 1177 (8th Cir. 2009) (noting that the NCIC

inaccurately stated that defendant had a prior conviction), with

United States v. Martínez-Jiménez, 464 F.3d 1205, 1209–12 (10th

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We hold that it was simply not enough for the district

court to have relied on the government's recitation of the sources

cited in the PSR without any additional inquiry into the

reliability of these sources. Unlike certified convictions or

other comparable judicial records that detail the fact of a

conviction and carry a presumption of reliability sufficient to

allow the government to meet its burden, see McKenzie, 539 F.3d at

19 (noting that government may satisfy its burden by producing a

certified copy of a conviction or another official court document);

Unger, 915 F.2d at 761 (same), we believe that non-judicial

records, such as those provided by the government here, should not

be afforded the same presumption.

The district court clearly erred by not requiring the

government to show that the PSR's description of the offense was

"'based on a sufficiently reliable source to establish the accuracy

of that description.'" See Brown, 510 F.3d at 75 (quoting Price,

409 F.3d at 444). In the absence of such an inquiry, the district

court could not have properly concluded that the government met its

burden.6
Cir. 2006) (noting that other circuits have approved the use of an

NCIC report to establish a prior conviction for sentencing purposes

and accepting the use of the NCIC report to establish the

defendant's conviction where the government also provided a letter

from the clerk of the court of conviction).

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ii. The Suffolk Superior Court Conviction

Bryant additionally challenges whether the government met

its burden to prove the fact of the Suffolk Superior Court

conviction.

Here, it is notable that Bryant does not challenge the

authenticity of the certified copy of the judicial record detailing

the Suffolk Superior Court conviction. Rather, Bryant, challenges

the fact of the conviction on grounds that a hand-written docket

sheet from the Boston Municipal Court, the court where the case

originated, puts into question the validity of the Suffolk Superior

Court conviction. The notation states, "SUCR9310760: Previous

record vacated. Superior Court Case is dismissed." Bryant

contends that this notation, though not from the court of

conviction, is nevertheless a judicial record of the originating

case that undermines the reliability of the Suffolk Superior Court

conviction for purposes of a sentencing enhancement.

The government defended the reliability of the judicial

record from the Suffolk Superior Court during the sentencing

hearing. The government noted that the official court record from

the court of conviction is a more dependable source than a handwritten notation from another court. In any event, the government
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contends that the district court did not clearly err in crediting

the government's argument. We agree.

Unlike its evidence supporting the fact of the New York

conviction, the government submitted a certified copy of a judicial

record to prove the fact of the Suffolk Superior Court conviction

from the court in which Bryant was convicted. As stated above, the

government can satisfy its burden through this type of judicial

record because it is presumptively reliable. See McKenzie, 539

F.3d at 19. Moreover, the record shows that the district court

carefully considered Bryant's argument, but nevertheless decided in

favor of the government. Thus, despite the existence of the

handwritten notation which admittedly added some confusion, we

cannot conclude that the district court clearly erred in finding

that the certified copy of the record from the Suffolk Superior

Court was sufficiently reliable to support the fact of Bryant's

Suffolk Superior Court conviction. "[A] district court's choice

between two plausible, but conflicting, interpretations of a

factual scenario cannot amount to clear error." United States v.

Carrasco, 540 F.3d 43, 49 (1st Cir. 2008) (alterations in original)

(quoting Valentín v. Hosp. Bella Vista, 254 F.3d 358, 367 (1st Cir.

2001)). 
Although we have not had occasion post-Shepard to apply the 7

categorical approach to controlled substance offenses, we have

stated pre-Shepard that "[t]he rationale on which the Taylor Court

relied in choosing a formal categorical approach is equally

applicable to controlled substance offenses." United States v.

Piper, 35 F.3d 611, 619 (1st Cir. 1994) (applying categorical

approach to controlled substance offenses in career offender

guideline context). We see no reason post-Shepard why we should

not continue to apply the categorical approach to controlled

substance offenses under U.S.S.G. § 4B1.2. We note other circuits

have applied the categorical approach to controlled substance

offenses post-Shepard. See, e.g., United States v. Savage, 542

F.3d 959, 964 (2d Cir. 2008).

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2. Prior Controlled Substances Convictions as

Career Offender Predicates

i. New York Conviction 

Under the Sentencing Guidelines, a "controlled substance

offense" is "an offense . . . punishable by imprisonment for a term

exceeding one year, that prohibits the manufacture, import, export,

distribution, or dispensing of a controlled substance . . . or the

possession of a controlled substance . . . with intent to

manufacture, import, export, distribute or dispense." U.S.S.G.

§ 4B1.2(b) (emphasis added). Thus, the definition of "controlled

substance offense" requires that the statute under which the

defendant was charged involves an intent to distribute or other

indicia of trafficking.7

Bryant argues in the alternative that if the government

has met its burden to prove the fact of the New York conviction, it

nevertheless failed to prove that the New York conviction for

attempted criminal sale of a controlled substance necessarily
 Although the government argues that this argument is waived 8

because it was not raised below, we nevertheless review Bryant's

claim in the event the district court on remand determines the fact

of the New York conviction to be sufficiently reliable. We do so

in the interest of judicial efficiency.

 U.S.S.G. § 2K2.1 of the guidelines states that the definition of 9

"controlled substance offense" has the meaning contained within

U.S.S.G. § 4B1.2. See U.S.S.G. § 2K2.1, cmt. n.1.

 The Connecticut Statute provides: 10

Any person who manufactures, distributes,

sells, prescribes, dispenses, compounds,

transports with intent to sell or dispense,

possesses with intent to sell or dispense,

offers, gives or administers to another person

any controlled substance . . . may, for the

first offense . . . be imprisoned not more

than seven years . . . .

Conn. Gen. Stat. § 21a-277(b).

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qualifies as a career offender predicate. Bryant bases his 8

argument on the Second Circuit's decision in Savage. See 542 F.3d

at 965-66.

In Savage, the Second Circuit reviewed a district court's

decision to apply a sentencing enhancement, pursuant to U.S.S.G.

§ 2K2.1(a)(2). Id. at 960. The district court in that case 9

based its decision, in relevant part, on its determination that one

of the defendant's prior felony convictions under Conn. Gen. Stat.

§ 21a-277(b) was for a "controlled substance offense," as the term

is defined in U.S.S.G § 4B1.2(b). Id. In reversing the district 10

court decision, the Savage court expressed its concern that an

offer to sell under Connecticut law could include a fraudulent
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offer which would mean that the person making the fraudulent offer

would not have the intent to distribute or sell an item. Id. at

965. Thus, it reasoned that the "Connecticut statute, by

criminalizing a mere offer to sell, criminalizes more conduct than

falls within the federal definition of a controlled substance

offense." Id. at 966. The Savage court further concluded that the

defendant's sentence should be vacated "[b]ecause nothing in the

statute of conviction, the charging document, the plea colloquy or

other comparable judicial record established with certainty that

[the defendant] necessarily pleaded guilty to the elements of a

controlled substance offense . . . ." Id. at 960.

Bryant argues that the statute upon which the New York

conviction is based, like the Connecticut statute, criminalizes

conduct that falls outside the federal definition of a controlled

substance offense. Bryant argues that because the New York statute

defines "sale" of a controlled substance to include "offer," it

criminalizes both predicate and non-predicate conduct. See N.Y.

Penal Law § 220.00(1) ("'Sell' means to sell, exchange, give or

dispose of to another, or to offer or agree to do the same.").

Bryant claims that because the government failed to show the New

York conviction was for conduct that would constitute a predicate

offense, it cannot be used for career offender purposes.

Bryant's argument fails because it is well-established

under New York law that "'in order to support a conviction under an
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offering for sale theory, there must be evidence of a bona fide

offer to sell -- i.e., that defendant had both the intent and

ability to proceed with the sale.'" People v. Samuels, 780 N.E.2d

513, 515 (N.Y. 2002) (quoting People v. Mike, 706 N.E.2d 1189, 1191

(N.Y. 1998)); see also People v. Gondolfo, 405 N.Y.S.2d 890, 894-95

(N.Y. Sup. Ct. 1978). Thus, the instant case is distinguishable

from Savage because concerns that Bryant could have been convicted

for making a fraudulent offer, a non-predicate offense, do not

exist here. At the time Bryant was allegedly convicted of the

offense, he would have been found to have intent to proceed with a

sale. It follows then that the New York conviction qualifies as a

predicate offense under U.S.S.G. § 4B1.2, which requires an "intent

to manufacture, import, export, distribute, or dispense." U.S.S.G.

§ 4B1.2(b).

ii. Suffolk Superior Court Conviction

Bryant also challenges the Suffolk Superior Court

conviction on the grounds that the government has failed to prove

that he pleaded guilty to acts that would constitute a career

offender predicate. In 1992, Bryant was initially charged with one

count of trafficking in cocaine in violation of Mass. Gen. Laws ch.

94C, § 32E(b)(1), and one count of conspiracy to violate the drug

laws of the Commonwealth (specifically, to traffic in cocaine) in

violation of Mass. Gen. Laws ch. 94C, § 40. The trafficking
 The statute states as follows: 11

Whoever conspires with another person to

violate any provision of this chapter [Chapter

94C Controlled Substances Act] shall be

punished by imprisonment or fine, or both,

which punishment shall not exceed the maximum

punishment prescribed for the offense, the

commission of which was the object of the

conspiracy.

Mass. Gen. Laws ch. 94C, § 40.

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charge was dismissed and Bryant pleaded guilty only to the

conspiracy charge.

Where the predicate offense involves a conspiracy, the

sentencing court must determine whether the object of the

conspiracy falls within the scope of U.S.S.G. § 4B1.2(b). See

Piper, 35 F.3d at 619 ("To determine the status of a conspiracy

conviction vis-a-vis the career offender rubric, the key question

is 'conspiracy to do what?'"). Bryant correctly argues that the

statute of conviction encompasses both conduct that would

constitute a predicate offense and conduct that would not.11

Therefore, the sentencing court is required to determine whether

the guilty plea, defined by a more expansive statute, necessarily

admitted the elements of a controlled substances offense for career

offender purposes. See Shepard 544 U.S. at 20–21. As noted above,

to make this determination in a case involving a guilty plea, the

sentencing court may review the "statutory definition, charging

document, written plea agreement, transcript of plea colloquy, and
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any explicit factual finding by the trial judge to which the

defendant assented." Id. at 16.

In this case the indictment underlying the Suffolk

Superior Court conviction demonstrated that the object of the

conspiracy fell within the scope of a controlled substances offense

under U.S.S.G § 4B1.2(b). It stated that Bryant "did conspire

. . . to unlawfully, knowingly and intentionally possess with

intent to distribute a net weight of fourteen grams or more of a

mixture containing cocaine . . . ." (emphasis added).

Reliance upon the indictment is also consistent with our

precedent. See Santos, 363 F.3d at 24 ("Where the charging

instruments are instructive on the issue of whether a predicate

offense [falls within the scope of § 4B1.2], we need not look

further.") (citation omitted); United States v. Leavitt, 925 F.2d

516, 517–18 (1st Cir. 1991) (citing to the Sentencing Guidelines

commentary to justify looking to the indictment to decide whether

conduct can be a predicate offense for career offender purposes if

it falls under a statute broad enough to encompass other conduct

that would not be a predicate offense for career offender

purposes).

We conclude that since the indictment clearly narrowed

the charge to a crime that qualifies as a controlled substances

offense for career offender purposes and Bryant pleaded guilty to
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the same, the Suffolk Superior Court conviction qualifies as a

career offender predicate offense.

C. Relevant Conduct Determination

Bryant finally argues that the district court erred in

determining that the uncharged sale of 0.7 grams of crack cocaine

on August 2, 2006 constituted "relevant conduct" under the

Sentencing Guidelines. The Sentencing Guidelines allow a

sentencing judge, when determining drug quantity, to include all

amounts "that were part of the same course of conduct or common

scheme or plan as the offense of conviction," whether or not the

defendant has been charged with those transactions. U.S.S.G.

§ 1B1.3(a)(2); see also United States v. Santos Batista, 239 F.3d

16, 20–21 (1st Cir. 2001). "For two or more offenses to constitute

part of a common scheme or plan, they must be substantially

connected to each other by at least one common factor, such as

common victims, common accomplices, common purpose, or similar

modus operandi." U.S.S.G. § 1B1.3, cmt. n.9(A). If two offenses

are not part of a common scheme or plan, they may still qualify as

the same course of conduct. U.S.S.G. § 1B1.3, cmt. n.9(B). For

two offenses to constitute part of the same course of conduct, they

must be "sufficiently connected or related to each other as to

warrant the conclusion that they are part of a single episode,

spree, or ongoing series of offenses." Id. The factors to be

considered "include the degree of similarity of the offenses, the
 See United States v. Hahn, 960 F.2d 903, 910-11 (9th Cir. 1992) 12

(holding that two instances of conduct were "relatively remote"

from one another because of a five-month gap); United States v.

Mullins, 971 F.2d 1138, 1144 (4th Cir. 1992) (concluding that

temporal proximity factor was "extremely weak" where gap of six

months existed between uncharged conduct and conduct underlying

offense of conviction); but see United States v. Moore, 212 F.3d

441, 446 (8th Cir. 2000) (upholding two instances of conduct as

same course of conduct where they were "just" four to six months

apart from one another).

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regularity (repetitions) of the offenses, and the time interval

between the offenses." Id. "When one of the above factors is

absent, a stronger presence of at least one of the other factors is

required." Id.

1. The August and November Drug Transactions

Here, we must determine whether the district court erred

in concluding that the uncharged drug transaction on August 2, 2006

was part of the same course of conduct as the transaction Bryant

was charged with on November 15, 2006. As mentioned directly

above, the government can meet its burden by showing that the

offenses are similar to one another, that they occur with some

regularity, and that the offenses are not remote in time from one

another. In the present case, because there was no finding that

Bryant's drug dealing occurred with regularity -- only two

transactions are at issue here -- and because the two transactions

were arguably "relatively remote" in time from another, we must 12

focus our inquiry on the degree of similarity between the two

transactions, mindful of the fact that "a stronger presence" of
-27-

similarity is required due to the absence or weakness of the other

factors.

Turning then to the similarity between the transactions,

we note an important limiting principle that "'not every drug

transaction undertaken by every drug trafficker is necessarily

linked in a meaningful sense.'" Santos Batista, 239 F.3d at 21

(quoting United States v. Sklar, 920 F.2d 107, 111 (1st Cir.

1990)). The sentencing judge must "find a sufficient link between

the acts charged and those included for sentencing purposes." Id.

If the district court cannot find a sufficient link, "'offenses of

the same kind, but not encompassed in the same course of conduct or

plan, are excluded.'" Id. (quoting United States v. White, 888 F.2d

490, 500 (7th Cir. 1989)). We have remarked that "[i]solated acts

cannot be conjoined and drug quantities aggregated for sentencing

purposes without a rational basis." Sklar, 920 F.2d at 111.

While admittedly close, we hold that the district court

did not clearly err here. The record shows that the two

transactions possessed "distinctive similarities" with one another,

such as occurring in roughly the same location, involving roughly

the same quantity of crack cocaine, and involving a similar pattern

of conduct between Bryant and the undercover officer. See United

States v. Buchanon, 299 Fed. Appx. 903, 904-05 (11th Cir. 2008)

(unpublished) (holding that "distinctive similarities" between two

offenses require more than a "generic level of likeness") (citing
 We stress that the term "same course of conduct" is analytically 13

distinct from the term "common scheme or plan." "'The same course

of conduct concept . . . looks to whether the defendant repeats the

same type of criminal activity over time.'" United States v. Adams,

303 Fed. Appx. 926, 927 (2d Cir. 2008) (unpublished) (internal

quotation marks omitted) (quoting United States v. Burnett, 968

F.2d 278, 280 (2d Cir. 1992)).

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United States v. Maxwell, 34 F.3d 1006, 1011 (11th Cir. 1994)).

Moreover, contrary to Bryant's claims that these were two one-off

transactions, there is evidence linking the two transactions. Most

pointedly, during the November 15, 2006 transaction, Bryant

indicated that he recognized the officer from before and told the

officer that he would "take care of him" in response to the

officer's request that "he wanted the same thing as last time."

Bryant's references to his prior dealings with the officer belie

Bryant's contention that the two transactions were isolated

incidents bearing no relation to one another.13

Lastly, Bryant wrongly characterizes himself as merely a

"cheerleader" during the August 2, 2006 transaction and

unconvincingly argues that his conduct was not in furtherance of a

"jointly undertaken criminal activity" as set forth by the U.S.S.G.

§ 1B1.3(a)(1)(B). Notably, Bryant facilitated the transaction

between Alston and the officer by walking with Alston and the

officer to a corner where the transaction would take place. In

addition, he encouraged the officer to try the product because it

was of high quality; he told the officer that the drugs the officer
 Bryant's citation to United States v. Wood, 924 F.2d 399, 404 14

(1st Cir. 1991), where we held an uncharged transaction could not

be included as relevant conduct, is unavailing. In Wood, we

stressed that for the purposes of the relevant conduct analysis,

the defendant could not be held responsible for a deal completed by

the defendant's wife because the defendant "did not even know about

[the transaction] . . . until it was over." Id. We concluded that

including the transaction would be an impermissibly "broad

interpretation of § 1B1.3(a)(2)" and "significantly increas[ing]

[the defendant's] sentence based on a transaction in which he took

no part . . . could not have been contemplated within the

§ 1B1.3(a)(2) exception." Id. The instant case is readily

distinguishable from Wood because Bryant knew about and helped

facilitate the August 2, 2006 transaction.

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was purchasing were his; and he advised the officer how to hide the

drugs from police, whom Bryant suspected were in the area.14

We reiterate that the mere fact that Bryant engaged in a

prior uncharged drug sale is not by itself sufficient to support

the district court's relevant conduct finding. In addition, we are

cognizant of our warning that "courts must be careful to hold the

adjudicative balance steady and true, giving U.S.S.G. § 1B1.3(a)(2)

the scope which its letter commands while at the same time

resisting prosecutorial efforts aimed at enlarging it." Sklar, 920

F.2d at 111.

With this cautionary note in mind, we stress that the

keys to our ruling are the high degree of similarity between the

two transactions and Bryant's familiarity with both the officer and

the officer's drug request during the November 15, 2006 drug sale.

From these facts we cannot conclude that the district court

committed clear error in finding, by a preponderance of evidence,
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a sufficient link between the two transactions. Accordingly, the

district court did not clearly err in considering the August 2,

2006 transaction as part of the same course of conduct as the

November 15, 2006 transaction for purposes of sentencing.

III. Conclusion

For the foregoing reasons, we conclude that the district

court did not commit clear error in finding that the August 2, 2006

transaction constituted relevant conduct. Also, we conclude that

the Suffolk Superior Court conviction and the New York conviction,

if proven, qualify as predicate offenses for career offender

purposes. However, we hold that the district court committed clear

error in finding that the government met its burden to establish

the existence of the prior New York conviction. We therefore

vacate Bryant's sentence and remand for further proceedings

consistent with this opinion.

Vacated and Remanded.

"Concurring opinion follows"
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HOWARD, Circuit Judge (concurring in part and concurring

in the judgment). I join the majority's analysis in all respects

except as to the reliability of the records of conviction. As to

that issue, I join in the judgment. I think the best view of the

record of the sentencing hearing is that, when the district court

concluded that the government had provided sufficient evidence to

demonstrate that Bryant was convicted of the New York offense, the

court necessarily concluded that the NCIC, NYSPIN, and correctional

records were reliable. Bryant had clearly challenged these

documents in particular, arguing that they could not be relied upon

to prove the fact of conviction, and, moreover, the district court

had actual copies of the correctional department records and an

NCIC report, so it was not limited to relying solely on the

government's recitation of the sources cited in the PSR.

That said, I won't quarrel with the majority's decision

to require an express reliability inquiry on remand in this case.

When it comes to that inquiry, I am inclined to think that criminal

history reports such as an NCIC report will suffice to prove the

fact of conviction, especially at a sentencing hearing in which the

defendant, like Bryant here, makes no claim that he is not the

subject of the NCIC report. See United States v. Servin-Acosta,

534 F.3d 1362, 1265 (10th Cir. 2008).