Of the District of the District of Columbia, sitting by *

designation.

United States Court of Appeals

For the First Circuit

No. 06-2354

UNITED STATES OF AMERICA,

Appellee,

v.

CHRISTOPHER WARD,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Michael A. Ponsor, U.S. District Judge]

Before

 Lipez and Howard, Circuit Judges,

and Oberdorfer, Senior District Judge. *

Chauncey B. Wood, with whom Shea, Larocque & Wood, was on

brief, for appellant.

Steven H. Breslow, Assistant United States Attorney, with

whom Michael J. Sullivan, United States Attorney, and Randall E.

Kromm, Assistant United States Attorney, was on brief, for

appellee. 

February 29, 2008
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LIPEZ, Circuit Judge. Focusing on deficiencies in a

state court plea colloquy on the issue of voluntariness,

Christopher Ward challenges on appeal his sentence of 120 months in

prison for several drug-related convictions. Ward argues that his

sentence is unreasonable as a matter of law because the district

court relied on unconstitutional prior state convictions as the

basis for a mandatory sentence enhancement under 21 U.S.C. §

841(b)(1)(A). In assessing this claim, we must consider the

decision of the Supreme Court in Boykin v. Alabama, 395 U.S. 238

(1969), which held that the acceptance of a plea of guilty "must be

based on a 'reliable determination on the voluntariness issue which

satisfies the constitutional rights of the defendant.'" Id. at 242

(quoting Jackson v. Denno, 378 U.S. 368, 387 (1964)). Boykin also

held that "[w]e cannot presume a waiver of these . . . important

federal rights from a silent record." Id. at 243.

After considering Boykin and cases decided in its wake,

we conclude that the record of the state court proceeding in this

case contained sufficient evidence to permit the district court to

find that Ward entered his state plea voluntarily, and hence the

mandatory sentence enhancement applied.

I.

We recite Ward's background from the Presentence Report

prepared in conjunction with his federal sentencing. The facts are
-3-

largely undisputed, and we specifically note where Ward contests

the statement of facts offered in the report.

Ward was born in 1986 to a mother who had been using

cocaine and methadone. Hospital records reveal positive tests for

cocaine, barbiturates, and hepatitis B antibodies on his umbilical

cord. At eighteen months, Ward was adopted by Mary Little, whom he

believes is a relative of his mother. Ward has not remained in

contact with his birth mother, and believes that she died in 2003

from complications related to AIDS; in addition, he does not know

his father. Raised in the Mason Square area of Springfield,

Massachusetts, a low-income neighborhood plagued by violence,

drugs, and gangs, Ward was arrested at age sixteen for receiving a

stolen motor vehicle, a charge that was subsequently dropped by the

authorities.

Seeking to improve his life, Ward used a friend's address

to enroll at a better school, West Springfield High School, and

relied on various means of transportation to attend school. His

true residency was soon discovered by administrators, and he was

forced to leave West Springfield High School prior to completing

the eleventh grade. He has since attempted to complete high

school, but has ultimately failed to do so. Near his eighteenth

birthday, Ward moved out of Mary Little's home and began to live

with friends and acquaintances in the Springfield area. In July
-4-

2004, Ward moved in with Emilia Rodriguez, with whom he now shares

a two-year-old child.

In May 2003, Ward was arrested by the Springfield Police

Department on the drug charges that serve as the basis for the

sentence enhancement Ward challenges in this appeal. Specifically,

on the basis of separate incidents, Ward was charged with several

counts of felony drug possession and distribution, three counts of

drug violation near a school zone or park, and one count each of

resisting arrest and refusing to identify oneself to the police.

In February 2004, Ward and his attorney reached an agreement with

the prosecutors to have the school zone drug violations nol prossed

in return for Ward's plea of guilty to the remaining charges. The

parties did not agree on any sentence recommendation to be offered

to the court. Ward accepted the deal and pleaded guilty to the

charges in the Springfield Division of the Massachusetts State

District Court.

Prior to accepting Ward's plea, the court conducted a

colloquy to determine whether his plea would be entered knowingly

and voluntarily, and if there was a sufficient factual basis for

the plea.

Court: Okay Mr. Ward, how old are you sir?

Ward: Seventeen.

Court: How far have you gone in school?

Ward: I'm in the eleventh grade.

Court: Have you had any alcohol or drugs today that

would in any way interfere with your ability

to understand this matter?

Ward: No.
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Court: Do you suffer from any mental illness,

disease or defect that would in any way

interfere with your ability to understand

this matter?

Ward: No.

Court: Do you understand that you're giving up your

right to a trial by a jury?

Ward: Yes.

Court: You're giving up your right to confront and

cross examine the witnesses against you and

you're giving up the right against selfincrimination. Do you understand those

rights?

Ward: Yes.

Court: Do you understand that you're giving them up

here today?

Ward: Yes.

Court: Do you understand that if you're not a

citizen of the United States, conviction of

this offense may have consequences with

regard to deportation, exclusion from

admission to the United States or denial of

naturalization? Do you understand that sir?

Ward: Yes.

Court: In other words, if you're not a citizen. . .

this only applies if you're not a citizen of

the U.S., but it would affect your

immigration, naturalization, and deportation

status. Have you had enough time to discuss

this matter with your attorney?

Ward: Yes.

Court: Has he explained to you the elements of the

offense the Commonwealth has to prove

against you?

Ward: Yes.

Court: Are you satisfied that he's given you his

best professional advice?

Ward: Yes.

Court: There are not agreed recommendations; I'm

free to impose whatever penalty I see fit.

But if I should exceed the recommendation

your attorney makes, this is what they were

referring to earlier, I would allow you to

withdraw your admission and go to trial in

front of another judge or jury. Do you

understand that?

Ward: Yes.
-6-

Per the court's request, Assistant District Attorney

Leahy then summarized the facts in the police report. Upon

completion of the recitation, the Court stated the following:

Court: Mr. Ward, you're admitting to four counts of

distribution of cocaine and one count of

distribution of marijuana and one count of

resisting arrest. Correct sir?

West (Ward's attorney): I believe three counts of

distribution of cocaine, Judge.

Leahy: One was possession with intention to

distribute cocaine.

West: Possession with intent.

Court: Okay, thank you. Is that what occurred sir

on those respective dates?

Ward: Yes.

Court: I find that you freely, voluntarily, and

willingly waived your rights and admitted to

sufficient facts in the complaint.

Assistant District Attorney Leahy then gave the Court a

summary of the facts in connection with a separate drug possession

charge and various motor vehicle offenses. Upon completion of the

recitation, the colloquy continued as follows:

Court: Is that what occurred on that date sir?

Ward: Yes.

Court: On this matter I also find that you freely,

voluntarily, and willingly waived your

rights and admitted to sufficient facts.

The Court accepted Ward's plea and sentenced him to one year of

probation.

In addition to and contemporaneously with the colloquy,

Ward, Ward's attorney, and the sentencing judge signed a preprinted waiver of rights in connection with the plea hearing. The

document included the disposition of each crime charged against
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Ward and language addressing the constitutional rights Ward waived

by pleading guilty. Additionally, the waiver form included

specific language concerning the voluntariness of the plea. The

relevant portion of the form signed by Ward states:

My guilty plea or admission is not the result of force or

threats. It is not the result of assurances or promises,

other than any agreed-upon recommendation by the

prosecution as set forth in Section I of this form. I

have decided to plead guilty, or admit to sufficient

facts, voluntarily and freely.

In addition, Ward's counsel certified on the form that he had

explained to Ward the consequences of his waiver, "so as to enable

the defendant to tender his or her plea of guilty or admission

knowingly, intelligently and voluntarily." Lastly, the judge

signed the waiver form, attesting that "after an oral colloquy with

the defendant, . . . the defendant has knowingly, intelligently and

voluntarily waived all of his or her rights as explained during

these proceedings and as set forth in this form." The language of

the waiver indicates that the judge signed the form at the

completion of the plea proceeding, although it is unclear whether

Ward and his attorney signed it prior to the proceeding or during

it.

 In July 2005, Ward was arrested for selling crack

cocaine on several occasions to an undercover Massachusetts state

trooper. A federal grand jury returned an indictment with two

counts of possession with intent to distribute and distribution of

crack cocaine in violation of 21 U.S.C. § 841(a)(1). In December
 Under Massachusetts law, a motion for a new trial is the 2

appropriate way to attack the validity of a guilty plea. E.g.,

Commonwealth v. Colon, 789 N.E.2d 566, 570 (Mass. 2003).

 Rule 12(c)(5) of the Massachusetts Rules of Criminal 3

Procedure states that "[t]he judge shall conduct a hearing to

determine the voluntariness of the plea or admission and the

factual basis of the charge." 

Ward has not raised all of these concerns in this collateral 4

proceeding. In fact, on appeal, he focuses only on deficiencies in

the state court colloquy on the issue of voluntariness. 

-8-

2005, the government filed an information under 21 U.S.C. §

851(a)(1), stating its intent to use Ward's prior state drug

convictions to increase his punishment. Additionally, in March

2006, the government filed a superseding information, alleging

additional charges against Ward. He pleaded guilty to all four

counts in the superseding information.

In May 2006, prior to being sentenced on these federal

charges, Ward filed a motion for a new trial in Springfield

District Court on the 2003-2004 state charges, claiming that the 2

state trial court had failed to comply with Rule 12 of the

Massachusetts Rules of Criminal Procedure and Massachusetts case

law on the requirements for accepting a guilty plea. Ward also 3

alleged in an affidavit submitted to the Springfield District Court

that he did not appreciate the consequences of his guilty plea,

that the court did not explain to him the elements of the crimes to

which he plead, and that neither the court nor his attorney did an

adequate job of explaining his rights to him. Ward likewise 4
 United States Sentencing Guidelines § 5G1.1(b) states that 5

"[w]here a statutorily required minimum sentence is greater than

the maximum of the applicable guideline range, the statutorily

required minimum sentence shall be the guideline sentence."

-9-

challenged in federal court the government's request for a sentence

enhancement based on these prior state convictions.

On August 8, 2006, the state court denied Ward's motion

and made no findings in support of its decision. The federal

district court held a sentencing hearing after the state court's

denial and concluded that the prior convictions were not impaired

by any constitutional violation. The previous convictions

triggered a mandatory minimum sentence under 21 U.S.C. § 841

(b)(1)(A) of 120 months. Because of U.S.S.G. § 5G1.1(b), this 5

mandatory minimum sentence also became the Guidelines sentence.

Ward was sentenced to 120 months imprisonment on each count, to be

served concurrently. If the enhanced minimum sentence had not

applied, the Guidelines range, according to the PSR, would have

been 57 to 71 months, and the mandatory minimum sentence would have

been 60 months rather than 120 months. The court additionally

sentenced Ward to eight years of supervised release.

Ward now appeals the sentence, asserting that the

district court committed reversible error by denying his motion to

exclude the prior state court convictions as the basis for a

sentence enhancement pursuant to 21 U.S.C. § 851. Specifically, he

contends that the state court record did not contain sufficient

evidence to permit the district court to find that he entered his
 Although we acknowledge that the question of whether a 6

guilty plea is voluntary may implicate the related questions of

whether the defendant had knowledge of the crimes charged, the

consequences of his plea, and the constitutional rights he was

waiving, we define "voluntariness" for purposes of this opinion to

include only the requirement that a plea be a free and deliberate

act that is not compelled or induced by force, coercion, threats,

or undue promises. See Boykin, 395 U.S. at 243 (quoting McCarthy

v. United States, 394 U.S. 459, 466 (1969)). Also, both parties

have conceded on appeal that other constitutional requirements

apart from voluntariness so defined have been satisfied in this

case.

-10-

guilty plea to the state charges voluntarily. Ward asks us to 6

vacate his sentence and order his resentencing by the district

court without consideration of the invalid state court convictions.

II.

The federal enhancement statute upon which the government

relied, 21 U.S.C. § 851, sets forth the procedures for using prior

convictions as sentence enhancements. The statute also permits

defendants to contest the validity of a prior conviction to prevent

it from serving as the basis for an enhanced sentence. For

constitutional challenges, a defendant must "file a written response

to the information" that "set[s] forth his claim, and the factual

basis therefor, with particularity . . . ." Id. § 851(c)(1)-(2);

see Custis v. United States, 511 U.S. 485, 491 (1994) (highlighting

Congress's intent in 21 U.S.C. § 851(c) to allow challenges to the

validity of a prior conviction used to enhance a federal drug

offense sentence). After receiving the defendant's response, the

court "shall hold a hearing," at which either party may produce
 The district court engaged in no independent fact-finding in 7

reaching its conclusion on the constitutionality of Ward's plea.

-11-

evidence, "to determine any issues raised by the response which

would except the person from increased punishment." 21 U.S.C. §

851(c)(1). For constitutional challenges, the defendant has the

burden to prove all issues of fact raised by the response by a

preponderance of the evidence. Id. § 851(c)(2).

Based solely on the state court record of the plea

proceeding, with no additional evidence bearing on the voluntariness

of Ward's plea offered by either party, the district court found

that "the record from the transcript [was] more than adequate to

support the voluntariness and all of the other criteria that is

attached to a plea proceeding." We review this legal determination

de novo. See Marshall v. Lonberger, 459 U.S. 422, 431 (1983) 7

("[T]he governing standard as to whether a plea of guilty is

voluntary for purposes of the federal Constitution is a question of

federal law . . . and not a question of fact . . . ."); see also

United States v. Walker, 160 F.3d 1078, 1095-96 (6th Cir. 1998)

("[T]he ultimate question whether a plea was voluntary requires a

legal conclusion.").

III.

In Boykin v. Alabama, an African-American defendant was

indicted on five counts of common law robbery for a series of armed

robberies that occurred in Mobile, Alabama. Three days after Boykin
 To satisfy the requirements of due process, it has been long 8

established that a guilty plea must in fact be knowing,

intelligent, and voluntary. See, e.g., McCarthy, 394 U.S. at 466

("[I]f a defendant's guilty plea is not equally voluntary and

knowing, it has been obtained in violation of due process and is

therefore void.").

-12-

received appointed counsel, he was arraigned and pleaded guilty to

all of the charges. He was sentenced to death on each of the

counts. The record of the proceeding revealed that "the judge asked

no questions of petitioner concerning his plea, and [the] petitioner

did not address the court." Boykin, 395 U.S. at 239. On appeal

from the Alabama Supreme Court, which had upheld on a 4-3 vote the

constitutionality of defendant's plea, the United States Supreme

Court reversed the decision and concluded that "[i]t was error,

plain on the face of the record, for the trial judge to accept

petitioner's guilty plea without an affirmative showing that it was

intelligent and voluntary." Id. at 242. The Court reached this 8

decision despite petitioner Boykin's silence in front of the Alabama

Supreme Court and in his petition and brief to the Supreme Court as

to whether the plea was, in fact, unknowing and involuntary. See

id. at 246 (Harlan, J., dissenting) ("In [Boykin's] petition and

brief in this Court, and in oral argument by counsel, petitioner has

never asserted that the plea was coerced or made in ignorance of the

consequences.").

With scant recognition of its dual audience, Boykin

simultaneously speaks to judges who accept guilty pleas and judges

who later review challenges to the constitutional adequacy of those
 Boykin has been the subject of sharp criticism. One judge 9

has noted that "[t]he Supreme Court's decision in Boykin v. Alabama

demonstrates the mess that can result from failure to identify the

holdings of a meandering opinion which makes assertions on

questions not before the court." Pierre N. Leval, Judging Under

the Constitution: Dicta About Dicta, 81 N.Y.U. L. Rev. 1249, 1269

(2006).

 In reaching this conclusion, the Court extended to the 10

guilty plea setting its holding in Carnley v. Cochran, 369 U.S.

506, 516 (1962), that due process requires a record showing of

defendant's decision to waive his right to counsel. See Boykin,

395 U.S. at 242. 

-13-

pleas, either on direct appeal or in collateral proceedings.9

Boykin reminds trial judges that a defendant's plea of guilty "must

be based on a 'reliable determination on the voluntariness issue

which satisfies the constitutional rights of the defendant.'" Id.

at 242 (quoting Denno, 378 U.S. at 387). Boykin reminds judges

reviewing challenges to the constitutional adequacy of a plea

proceeding that due process requires that the record of the

proceeding contain sufficient evidence to support the trial court's

decision to accept the plea. Id. at 243 ("We cannot presume a 10

waiver . . . from a silent record."); see Brady v. United States,

397 U.S. 742, 747 n.4 (1970) ("The new element added in Boykin was

the requirement that the record must affirmatively disclose that a

defendant who pleaded guilty entered his plea understandingly and

voluntarily.").

Given this new element, with its focus on the adequacy of

the record that memorializes the plea proceeding, the fact of

voluntariness cannot be inferred by a reviewing court from a silent
-14-

or otherwise inadequate record. Instead, due process requires that

there be an "affirmative showing" in the record to support that

determination. Boykin, 395 U.S. at 242; see Hanson v. Phillips,

442 F.3d 789, 801 (2d Cir. 2006) ("It may well be that [the

defendant], in fact, understood his alternatives, but we are unable

to conclude so based on this record, and it is the trial court's

responsibility to ensure 'a record adequate for any review that may

be later sought.'" (quoting Boykin, 395 U.S. at 244)). Indeed, the

Supreme Court highlighted in Boykin the importance of maintaining

an adequate record for the appeals process. Id. at 244 ("When the

judge [ensures a plea is knowing and voluntary], he leaves a record

adequate for any review that may be later sought, and forestalls the

spin-off of collateral proceedings that seek to probe murky

memories.") (citations omitted).

Despite Boykin’s requirement of an "affirmative showing"

in the record that a plea was knowing and voluntary, Boykin does not

address the contours of that showing. In arguing that the record

of the state plea proceeding was inadequate, Ward takes his cue from

Justice Harlan’s dissent in Boykin. See 395 U.S. at 245 ("The Court

thus in effect fastens upon the States, as a matter of federal

constitutional law, the rigid prophylactic requirements of Rule 11

of the Federal Rules of Criminal Procedure."). He suggests that the

contours of the Boykin showing are defined (that is,

constitutionalized) by the requirements of Federal Rule of Criminal
 At the time Boykin was decided, Rule 11 consisted of four 11

sentences:

A defendant may plead not guilty, guilty or, with the

consent of the court, nolo contendere. The court may

refuse to accept a plea of guilty, and shall not accept

such plea or a plea of nolo contendere without first

addressing the defendant personally and determining that

the plea is made voluntarily with understanding of the

nature of the charge and the consequences of the plea.

If a defendant refuses to plead or if the court refuses

to accept a plea of guilty or if a defendant corporation

fails to appear, the court shall enter a plea of not

guilty. The court shall not enter a judgment upon a plea

of guilty unless it is satisfied that there is a factual

basis for the plea.

Fed. R. Crim. P. 11. Since 1969, Rule 11 has been amended on

numerous occasions, each time placing different or additional

obligations on the federal courts. Most notably, the Rule was

amended in 1974 in response to the Boykin decision to require

courts to more specifically identify the constitutional rights that

are relinquished pursuant to a guilty plea. Fed. R. Crim. P. 11

advisory committee's notes (1974 amendments).

-15-

Procedure 11. To this end, he cites the Supreme Court's decision 11

in McCarthy, which states that Rule 11's more strict colloquy

requirements can help "reduce the great waste of judicial resources

required to process the frivolous attacks on guilty plea convictions

that are encouraged, and are more difficult to dispose of, when the

original record is inadequate." 394 U.S. at 472.

Supreme Court decisions contemporaneous with Boykin

preclude any argument that Boykin constitutionalized Rule 11. Two

months prior to Boykin, the Supreme Court stated that "the procedure

embodied in Rule 11 has not been held to be constitutionally

mandated." McCarthy, 394 U.S. at 465 (rejecting a guilty plea

because a district judge had failed to comply with the requirements
 In McCarthy, the district court had failed to comply with 12

the requirements of Fed. R. Crim. P. 11 by not "'first addressing

[the defendant] . . . personally and determining that the plea

[was] . . . made voluntarily with understanding of the nature of

the charge . . . ,' and (2) . . . enter[ing] judgment without

determining 'that there [was] . . . a factual basis for the plea.'"

394 U.S. at 462 (quoting Fed. R. Crim. P. 11). Because of this

deficiency, the Supreme Court held that the defendant was entitled

to plead anew; the Court rejected the government's request that the

case be remanded for an additional evidentiary hearing to show that

McCarthy's plea was knowing and voluntary. Id. at 464.

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of Fed. R. Crim. P. 11). The Court confirmed the non- 12

constitutional nature of its holding in McCarthy one month later,

noting that it was based "solely upon the application of Rule 11 and

not upon constitutional grounds." Halliday v. United States, 394

U.S. 831, 832 (1969). In deciding not to impose the Rule 11

requirements retroactively, the Court in Halliday let stand a plea

that we had ruled contained "'ample evidence' support[ing] the . .

. finding that the Government had met its burden of demonstrating

that petitioner entered his plea voluntarily with an understanding

of the nature of the charges against him," even though the plea did

not comply with Rule 11. Id. at 832; see, e.g., Stewart v. Peters,

958 F.2d 1379, 1384 (7th Cir. 1992) ("The Constitution does not

enact Rule 11 of the Federal Rules of Criminal Procedure . . . .");

Wade v. Coiner, 468 F.2d 1059, 1060 (4th Cir. 1972) ("[W]e do not

find in Boykin v. Alabama . . . a rule fastening the 'rigid

prophylactic requirements of Rule 11' of the Federal Rules of

Criminal Procedure upon the states.").
 What Boykin requires is different in kind than what Miranda 13

requires, although both serve similar prophylactic functions to

protect constitutional rights. See Adams v. Peterson, 968 F.2d

835, 846 (9th Cir. 1992) (Kozinski, J., concurring) ("Like Miranda

. . . , Boykin concentrates on providing additional, bright-line

protection for enumerated constitutional guarantees -- namely, the

rights to trial by jury, to confront one's accusers and to be free

from compulsory self-incrimination -- and thereby travels one step

beyond the specific requirements of the Constitution."). The

protection Boykin offers, however, is less bright than that imposed

by Miranda. Whereas Miranda requires a precise script to protect

a defendant’s right against self-incrimination, Boykin does not

mandate that a judge adopt specific procedures to create an

adequate record, or that the record contain specific, indispensable

-17-

Even if Boykin did not constitutionalize Rule 11, it

unmistakably held that a trial court must produce a record adequate

for a reviewing court to conclude that the constitutional

requirements of a plea have been met. See Hanson, 442 F.3d at 800

("While we recognize that no particular form or script is required

and that state courts have considerable leeway to establish a record

in whatever reasonable manner they see fit, Boykin established that

the record of a guilty plea must affirmatively disclose that the

defendant made his plea intelligently and voluntarily."). Such a

record may consist of a defendant's explicit answers during the plea

colloquy to inquiries concerning the defendant's understanding of

the nature of the charges, the consequences of pleading guilty to

the charges, and the rights being waived. That plea colloquy might

be supplemented by the completion of a printed waiver form that also

addresses the constitutional elements of a plea. A specific script,

a set of magic words, or even certain types of inquiries are not

required. See, e.g., Siegel v. New York, 691 F.2d 620, 626 (2d 13
elements. Boykin is satisfied so long as the record is sufficient

to allow a reviewing court to conclude that the defendant's plea

was constitutional. 

-18-

Cir. 1982) ("Rather than mandating a specific catechism, in

determining voluntariness and intelligence, due process requires

only that the courts provide safeguards sufficient 'to insure the

defendant what is reasonably due in the circumstances.'" (quoting

Santobello v. New York, 404 U.S. 257, 262 (1971))); see also Leval,

supra, at 1272 n.71 (citing numerous cases for the proposition that

Boykin, despite language in the opinion, did not require an oral

colloquy to explicitly demonstrate waiver of the three specific

constitutional rights addressed in the opinion).

With this understanding of Boykin in mind, we assess

whether the district court concluded correctly that the record of

Ward’s state court proceeding was "more than adequate to support"

the finding that Ward entered his state plea voluntarily.

IV.

In deciding whether there is an affirmative showing of

voluntariness in the state court record of Ward's plea, we examine

the totality of the circumstances surrounding the plea. Brady, 397

U.S. at 749 ("The voluntariness of Brady's plea can be determined

only by considering all of the relevant circumstances surrounding

it."). We are not limited to reviewing the transcript of the

colloquy alone, as the district court appears to have done, but may

also consider the other materials and documents that comprise the
-19-

record as a whole. See United States v. Vonn, 535 U.S. 55, 74

(2002) (finding that a court is not limited to the record of the

plea proceeding in determining whether a Rule 11 violation affects

defendant's substantive rights); Hanson, 442 F.3d at 799 (making a

Boykin determination by examining "the record as a whole").

The parties acknowledge on appeal that the state court

record supports a determination that Ward (1) had an understanding

of the charges against him; (2) was aware of the consequences of his

guilty plea; and (3) was competent to make such a plea. They

contest, however, whether the state court record contains sufficient

evidence to permit the district court to find that he entered his

guilty plea to the state charges voluntarily, free of coercion,

force, threats, or undue promises. Ward contends that the plea was

constitutionally deficient because the state court never inquired

generally whether his plea was a free and voluntary act, nor

specifically whether it was the product of coercion, undue promises,

or threats. Additionally, he argues that neither the presence of

counsel on his behalf nor the signed waiver form remedy the

deficiencies in the plea colloquy. Finally, he claims that his age

and unfamiliarity with the plea process provide additional support

for vacating the district court's sentencing decision, with its

reliance on the state court convictions.

The government responds that the district court was

correct to reject Ward's claim of unconstitutionality.
 As set forth in 21 U.S.C. § 851(c), a defendant may offer 14

evidence to challenge the constitutionality of a conviction invoked

by the government to enhance a federal drug sentence. See, e.g.,

United States v. Jackson, 121 F.3d 316, 319 (7th Cir. 1997)

("[Section] 851 was enacted [] to insure that defendants are given

reasonable notice and an opportunity to be heard, which includes

the opportunity to contest the evidence or challenge a prior

conviction if the defendant might be subject to a greater sentence

than would otherwise be imposed.").

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Acknowledging that the state court failed to explicitly address in

its colloquy whether Ward's plea was a free and voluntary act, the

government nonetheless asserts that, based on the totality of the

circumstances surrounding the plea, the record was sufficient to

support the district court’s voluntariness determination.

Specifically, it argues that the text of the colloquy engaged in by

the court and Ward, the presence of adequate counsel on Ward's

behalf, and the written waiver signed by Ward, his attorney, and the

presiding judge, offer adequate support for the district court's

determination that the plea was entered voluntarily.

We agree with the government that the record supports the

district court's inference that Ward's plea was freely and

voluntarily entered. In reaching this conclusion, we rely on the

waiver form signed by Ward contemporaneously with the plea

proceeding, the factual circumstances surrounding the plea, the text

of the colloquy itself, which contains no evidence suggesting that

Ward's actions were the product of any force, coercion, undue

promises, or threats, and Ward's failure to supply evidence of such

influences to the district court, as he was entitled to do.14
 In his affidavit submitted to the Springfield District Court 15

requesting a new trial, and in his response to the government's

notice to pursue a penalty increase under 21 U.S.C. § 851(a)(1),

Ward states that he did not appreciate the consequences of his

guilty plea, and that the court did not explain to him the rights

he was waiving by pleading guilty. Ward's own responses to

explicit questions in the colloquy, however, contradict these

assertions. When explicitly told by the state trial judge that he

was giving up the right to a trial by jury, the right to confront

and cross-examine witnesses and the right against selfincrimination, Ward responded that he understood those rights and

that he was giving them up by pleading guilty. Ward has not

submitted any other evidence in the course of these collateral

proceedings to support his assertions that he did not understand

the consequences of his guilty plea and the rights he was waiving.

Indeed, on appeal, Ward has only contested whether the state court

record is adequate to support the district court's determination

that his plea was entered voluntarily.

-21-

In the presence of the trial court and Ward's counsel,

Ward signed a waiver form addressing his rights. The form stated

that Ward’s guilty plea "[was] not the result of force or threats

. . . [nor] the result of assurances or promises, other than any

agreed-upon recommendation by the prosecution." By signing the

form, Ward also attested that he had "decided to plead guilty . . .

voluntarily and freely." Given Ward's education level –- he was in

eleventh grade at the time of the plea proceeding –- and ability to

respond appropriately to the judge during the colloquy, there is no

reason on this record to question his ability to understand the

written waiver and the consequences of his decision to sign it.15

The signature of Ward's counsel follows Ward's and affirms that he

explained to Ward "his waiver of jury trial and other rights so as

to enable [him] to tender his plea of guilty . . . knowingly,

intelligently, and voluntarily." Finally, the trial judge's
 We do not suggest that a written waiver alone can take the 16

place of a verbal colloquy between the court and a defendant.

Additionally, some jurisdictions use more comprehensive waiver

forms to assist them in satisfying the constitutional obligations,

including requiring detailed and/or hand-written responses to

questions posed. That seems a sensible practice.

-22-

signature attests that he found "after an oral colloquy with the

defendant, that [Ward] has knowingly, intelligently, and voluntarily

waived all of his rights as explained during [the plea] proceedings

and as set forth in this form."16

The text of the plea proceeding offers additional support

for our conclusion. The record of the plea does not suggest that

Ward was impaired in any manner that would impede his ability to

understand or respond to the questions posed by the judge. Ward did

not hesitate when acknowledging the rights he was waiving or when

admitting to the factual basis of the crimes he was charged with

committing. He never asked the judge to repeat a question or

statement. Also, Ward never halted the colloquy to pose a question

to his attorney or seek his advice on any matter. Neither Ward nor

his counsel objected or otherwise responded when the trial judge,

on all charges, found that Ward had "freely, voluntarily, and

willingly waived [his] rights and admitted to sufficient facts." 

Ward cites his age and inexperience in the criminal

justice system to support his claim that the plea colloquy was

inadequate on the voluntariness issue. These factors would be more

relevant if Ward was claiming that the plea colloquy was deficient

in its explanation of the nature of the charges, the constitutional
 The Court asked Ward three questions regarding his counsel 17

and their discussions. First, Ward was asked whether he "had

enough time to discuss this matter with [his] attorney?" Next, he

was asked whether his counsel "ha[d] explained to [him] the

elements of the offense the Commonwealth ha[d] to prove against

[him]?" Finally, the court asked Ward whether he was "satisfied

that [his attorney] has given his best professional advice?" Ward

answered "yes" to each of the questions. 

-23-

rights being waived, or the consequences of the plea. Such

explanations at the plea hearing itself are essential to a knowing

plea. Age and inexperience seem less relevant to the issue of

voluntariness in the absence of any evidence of external factors,

such as force, coercion, threats, or undue promises. As we have

indicated, the record of the state court proceeding does not suggest

the presence of any such factors, and Ward did not introduce any

evidence of such factors in this collateral proceeding. Also, so

far as we can tell from this record, and as Ward acknowledged in the

plea colloquy, Ward was represented by competent counsel throughout

the state proceeding. Such representation is an important factor 17

in the voluntariness analysis, and it supports the district court's

determination. See North Carolina v. Alford, 400 U.S. 25, 31 (1970)

(noting that a plea is more likely the product of a free and

rational choice where the defendant has the benefit of competent

counsel); Sophanthavong v. Palmateer, 378 F.3d 859, 876 (9th Cir.

2004) (Ferguson, J., dissenting) (noting the heightened role

competent counsel plays in the context of a juvenile making a plea).
-24-

V.

Boykin requires that the record of a guilty plea contain

an affirmative showing that there was a voluntary waiver by the

defendant of his constitutional rights. Although compliance with

a state version of Rule 11 in a state plea proceeding will almost

surely constitute such an affirmative showing, see Fed. R. Crim. P.

11, Boykin does not constitutionalize Rule 11 for state plea

proceedings. Moreover, although specific attention to the issue of

voluntariness in any plea proceeding is highly desirable, there is

no specific script that must be followed. Instead, in a collateral

proceeding under 21 U.S.C. § 851(c), where there is a constitutional

challenge to the voluntariness of a state court plea, the district

court can examine the totality of the circumstances surrounding the

plea.

Although the plea colloquy between the state trial court

and Ward did not contain specific questions addressing the voluntary

nature of Ward's plea, all of the relevant circumstances -- the

detailed colloquy between the court and Ward on issues other than

voluntariness, the clarity and directness of Ward's responses, the

involvement of effective counsel on Ward's behalf throughout the

proceedings, the written waiver signed by Ward, his counsel, and the

court, and the failure of Ward to produce any evidence of force,

coercion, threats, or undue promises -- convince us that the

district court ruled correctly that the state court record permits
-25-

an inference that Ward entered his guilty plea to the state charges

voluntarily. Put another way, the record of the state proceedings

includes the affirmative showing required by Boykin that Ward's plea

was entered voluntarily. Given this showing, the district court was

entitled to impose a sentence that included the statutory

enhancement. 

Affirmed.

- Concurring Opinion Follows -
-26-

OBERDORFER, J., concurring. The majority amply

establishes that the state-court record affirmatively showed that

Ward’s plea entered here was voluntary and legal. I write simply

to register my discomfort with the heavy sentences of imprisonment

(most recently 10 years mandatory) beginning when he was a 17-yearold victim of a flagrantly poisonous environment. Hopefully, the

efforts of insightful leaders such as the members of the bipartisan

Commission on Safety and Abuse in America’s Prisons (co-chaired by

former United States Attorney General Nicholas de B. Katzenbach and

the Honorable John Gibbons, former Chief Judge of the United States

Court of Appeals for the Third Circuit), will lead to significant

improvements in the federal prison environment, including physical,

psychological and educational opportunities for young, disadvantaged

inmates like Ward. See Commission on Safety and Abuse in America’s

Prisons, Confronting Confinement, at iii (2006) (“A year ago, a

group of individuals with little in common promised to recommend

strategies for operating correctional facilities that serve our

country’s best interests and reflect our highest values. Today, we

speak in a single voice about the problems, our nation’s ability to

overcome them, and the risks for all of us if we fail to act.”).

Should these services materialize and bear fruit in Ward’s case, it

would behoove his counsel and his probation officer to pursue

executive clemency for Ward before it is too late — if it is not

already.