United States Court of Appeals

For the First Circuit

No. 98-2178

UNITED STATES OF AMERICA,

Appellee,

v.

ANTONIO BIERD,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF MASSACHUSETTS

[Hon. William G. Young, U.S. District Judge]

Before

 Torruella, Chief Judge,

Coffin, Senior Circuit Judge,

and Stahl, Circuit Judge.

Laura C. Edmonds, by Appointment of the Court, for

appellant.

Allison D. Burroughs, Assistant U.S. Attorney, with whom

Donald K. Stern, United States Attorney, and Mark W. Pearlstein,

Assistant U.S. Attorney, were on brief for appellee.

June 28, 2000

1When entering an Alford guilty plea, a defendant is not

required to admit guilt. This procedure was authorized by the

Supreme Court in North Carolina v. Alford, 400 U.S. 25 (1970),

holding that "[a]n individual accused of crime may voluntarily,

knowingly, and understandingly consent to the imposition of a

prison sentence even if he is unwilling or unable to admit his

participation in the acts constituting the crime." Id. at 37.

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COFFIN, Senior Circuit Judge. Defendant Antonio Bierd pled

guilty to charges of money laundering, drug possession, and

related conspiracies. He now seeks vacation of his convictions

or, in the alternative, resentencing on the ground that his plea

was not knowing, voluntary, and intelligent, in part due to the

court's alleged improper participation in the plea negotiation

process. Defendant also argues that he should not have been

given a sentencing enhancement based on the court's finding that

he had knowledge that the funds he transmitted were drug

proceeds. Because we conclude that defendant's guilty plea was

valid and that the court did not err in sentencing him, we

affirm his convictions.

I. Factual Background

In April 1998, defendant entered an unconditional guilty

plea to drug possession with intent to distribute and a related

conspiracy and entered an Alford plea1 to three counts of money

laundering and a related conspiracy, based on the following

allegations made by the government.
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Co-defendant Francisco Objio owned two check cashing

businesses -- Best Video, in Brockton, Massachusetts, and Best

Money Exchange, in Jamaica Plain. Defendant managed Best Video

for Objio. Despite the fact that neither entity maintained a

foreign money transmittal license, defendant and Objio had

established a scheme by which they transferred money for others

to the Dominican Republic, employing various mechanisms designed

to avert reporting requirements because the funds were often

drug proceeds.

One user of their services was an undercover Massachusetts

state police officer posing as a drug dealer who delivered money

to defendant or Objio for transfer to the Dominican Republic on

three separate occasions in the fall of 1997. Each time the

officer dropped off money, in small denominations, he reiterated

the need for secrecy and spoke about the drug business and his

customers. Defendant and Objio allowed the officer to use a

false name and broke the large transactions into smaller amounts

to avoid reporting requirements.

Instead of depositing drug proceeds, generally large amounts

of cash, into the bank accounts of Best Video or Best Money

Exchange, the drug proceeds were used to cash third party

checks, which were then deposited into the bank accounts. To

transfer the money, Objio would contact his associate in the
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Dominican Republic, who held checks that were drawn on Best

Money Exchange's account and stamped with Objio's signature.

The checks in the Dominican Republic were then made payable to

persons other than the ultimate recipient, and after the checks

were cashed, the cash was delivered to the recipient intended by

the sender.

Defendant and Objio were also involved in drug trafficking.

Specifically, defendant helped arrange the purchase and transfer

of a kilogram of cocaine on one occasion in August 1997.

On the second day of the joint trial of defendant and Objio,

Objio renewed a severance motion, arguing that defendant's

defense that he was only following orders was in conflict with

his own. At sidebar, the district judge explained that he was

inclined to deny the motion and the following exchange occurred:

Court: There is no Nuremberg defense. If [defendant]

gets on the stand and says I followed orders, [he's]

guilty. And it's unclear to me, maybe not all the

charges, but these money laundering charges, it's

unclear to me if that's true if that's what's really

the defense. Why doesn't he plead out, get the three

levels he's entitled to and then that will accomplish

the severance, but that's not for me to say. That's

for - - - 

Defense counsel: That's exactly where I think we're headed.

Court: Well, if that happens, it happens. I have

nothing to say about it.

The next day, defendant entered his Alford and unconditional

guilty pleas and he was subsequently sentenced.
2In Anders v. California, 386 U.S. 738 (1967), the Supreme

Court explained that "if [a defendant's] counsel finds his case

to be wholly frivolous, after a conscientious examination of it,

he should so advise the court and request permission to

withdraw." Id. at 744.

3We also evaluate "(1) the plausibility of the reasons

prompting the requested change of plea; (2) the timing of the

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Defendant then appealed. His counsel filed an Anders brief2

and moved to withdraw. This court identified as non-frivolous

the issue of whether the trial judge violated Fed. R. Crim. P.

11(e)(1) by initiating a plea discussion and approved the

appointment of new counsel to represent defendant.

II. Whether Defendant's Plea was Knowing, Voluntary,

and Intelligent

Defendant's overarching argument is that his plea was not

voluntary as required by Fed. R. Crim. P. 11. First, defendant

alleges that the court violated Fed. R. Crim. P. 11(e)(1) by

participating in the plea negotiation process. Second,

defendant contends that the court coerced him into pleading

guilty by promising him a three level reduction in his base

offense level for acceptance of responsibility.

We review the totality of circumstances when considering a

request to withdraw a guilty plea, considering primarily whether

a defendant's guilty plea was "knowing, voluntary and

intelligent within the meaning of Rule 11." See United States

v. Cotal-Crespo, 47 F.3d 1, 3-4 (1st Cir. 1995).3 Rule 11
defendant's motion; [and] (3) the existence or nonexistence of

an assertion of innocence," United States v. Parrilla-Tirado,

22 F.3d 368, 371 (1st Cir. 1994), although these factors need

not be emphasized in this case because we find that the

defendant's plea was knowing, voluntary, and intelligent.

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embodies three "core concerns": "1) absence of coercion; 2) the

defendant's understanding of the charges; and 3) the defendant's

knowledge of the consequences of the guilty plea." United

States v. Gray, 63 F.3d 57, 60 (1st Cir. 1995).

Although defendant failed to raise his claim before the

trial court, "a Rule 11 challenge will not be deemed waived upon

a party's failure to raise it in the district court." United

States v. Parra-Ibanez, 936 F.2d 588, 593 (1st Cir. 1991). Rule

11(h) states that "[a]ny variance from the procedures required

by this rule which does not affect substantial rights shall be

disregarded." Furthermore, the advisory committee notes to the

1983 amendments to Fed. R. Crim. P. 32, which authorizes plea

withdrawal motions, explain that when a defendant moves for the

first time on appeal to set aside his guilty plea, "the

applicable standard is that stated in Hill v. United States, 368

U.S. 424 (1962): 'a fundamental defect which inherently results

in a complete miscarriage of justice' or 'an omission

inconsistent with the rudimentary demands of fair procedure.'"

We find that regardless of which standard is employed, the

court's statements did not constitute reversible error because,
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although they were arguably at "variance from the procedures

required" by Rule 11, they were not so egregious as to "affect

substantial rights" or constitute a "fundamental defect." 

Defendant first alleges that the court initiated a plea

discussion in violation of Fed. R. Crim. P. 11(e)(1)'s mandate

that "[t]he court shall not participate in any discussions

between the parties concerning any . . . plea agreement."

Defendant points to the exchange that occurred on the second day

of trial at sidebar when his co-defendant attempted to revisit

his severance motion. He explains that his counsel immediately

relayed this conversation to him, which prompted his desire to

change his plea to guilty.

The Rule 11(e)(1) prohibition "simply commands that the

judge not participate in, and remove him or herself from, any

discussion of a plea agreement that has not yet been agreed to

by the parties in open court." United States v. Bruce, 976 F.2d

552, 556 (9th Cir. 1992). This ban on judicial involvement in

the plea bargaining process furthers three goals. The primary

philosophy behind it is that "[j]udicial involvement in plea

negotiations inevitably carries with it the high and

unacceptable risk of coercing a defendant to accept the proposed

agreement and plead guilty." Id. at 556. Second, "the

interests of justice are best served if the judge remains aloof
4In Porcaro v. United States, 784 F.2d 38 (1st Cir. 1986),

this court remanded the defendant's appeal for further

proceedings on several bases, among them that the "trial judge's

making of a plea offer, if it occurred, would appear to have

violated Fed. R. Cr. P. 11(e)(1)." Id. at 42. And in Murchu v.

United States, 926 F.2d 50 (1st Cir. 1991), we remanded a

section 2255 petition for further proceedings to determine if

the court participated in off the record plea discussions.

See id. at 57.

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from all discussions preliminary to the determination of guilt

or innocence so that his impartiality and objectivity shall not

be open to any question or suspicion when it becomes his duty to

impose sentence." United States v. Werker, 535 F.2d 198, 203

(2d Cir. 1976). And third, the prohibition "preserves the

judge's impartiality after the negotiations are completed," for

example when assessing the voluntariness of a plea or presiding

over trial when a negotiation fails. See United States v.

Casallas, 59 F.3d 1173, 1178 (11th Cir. 1995) (citing Bruce, 976

F.2d at 556-57).

Because we find limited authority within the circuit

directly addressing a complaint that a judge improperly

participated in plea negotiations,4 we survey the case law to get

a flavor for the kinds of court statements that have been deemed

impermissible intervention. We conclude that the court's

language, although not definitively foreclosing the

interpretation that defendant suggests, was not so egregious as

to require vacation of the conviction.
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Improper participation resulting in vacation occurs, for

example, when a court comments on or mandates what it perceives

to be an appropriate penalty for a defendant in the context of

plea agreement discussions. See, e.g., United States v.

Crowell, 60 F.3d 199, 204 (5th Cir. 1995) (sentence vacated

because it was improper for court to indicate, while the parties

were negotiating a second agreement, that a penalty more severe

than that in the initial rejected agreement was necessary);

United States v. Anderson, 993 F.2d 1435, 1439 (9th Cir. 1993)

(plea vacated due to court's violation of the rule by its

"prospective refusal to accept a plea to fewer than the full

thirty counts, and direction to the prosecutor not to offer any

such deal in the future"). When a judge breached the rule by

stating, during a conference call with the prosecutor and

defense counsel that was intended to facilitate a plea bargain,

that "there is no way on God's green Earth I'm going to sentence

[defendant] to only seven years, and I think the likelihood is

I'm going to exceed the guidelines," the defendant's conviction

was set aside. United States v. Barrett, 982 F.2d 193, 194-96

(6th Cir. 1992). The defendants' guilty pleas were vacated when

the judge stated that he would be more comfortable if the

defendants were never released from jail and essentially crafted
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a more stringent plea agreement than that proposed. See United

States v. Miles, 10 F.3d 1135, 1138-40 (5th Cir. 1993). 

Further, when a trial judge threatens a defendant with a

higher sentence if he pursues his right to a trial instead of

pleading guilty, a defendant's plea must be vacated. For

example, it was improper for a judge to say to the defendants as

trial began: 

We don't play games in this court. Y'all want to

plead guilty, you can plead guilty today. If you

don't want to plead guilty, we'll go to trial. We

have got plenty of time to try them. That will give

each one of you until noon today to file any plea

agreements. After that you will plead straight up or

you go to trial. . . . They want to go out and get

arrested, they come in here and they'll get a fair

trial, and if they get found guilty, they'll also get

a fair sentence, fairly high.

United States v. Corbitt, 996 F.2d 1132, 1133-35 (11th Cir.

1993). And a trial judge transgressed the rule, resulting in

vacation of the defendants' convictions, when he repeatedly

urged the defendants to "think carefully" about the fact that

they faced life sentences upon conviction after trial, reminded

them that the penalty under the sentencing guidelines would be

"so heavy, so very, very heavy," and requested that the

prosecution leave the offer open to allow the defendants

additional time. See Bruce, 976 F.2d at 555, 558; see also

Casallas, 59 F.3d at 1177 (plea vacated when the court

emphasized to defendant who declined to plead guilty that he
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would receive a ten-year minimum sentence under the proposed

agreement but risked the fifteen-year mandatory minimum if he

were convicted after trial); cf. Crowell, 60 F.3d at 204 (no

violation of Rule 11 when the court, in evaluating a plea

agreement that had been presented, compared a defendant's

sentence under a proposed plea agreement with the potential

sentence upon conviction after trial).

On the other hand, in Blackmon v. Wainwright, 608 F.2d 183

(5th Cir. 1979), the court held that a trial judge's "off-thecuff" remarks concerning a possible sentence did not rise to the

"level of participation" envisaged by Rule 11. See id. at 184-

85. Further, when a court warned a defendant who indicated a

desire to plead guilty "of the obvious risk should he plead

guilty to the substantive offense and then go to trial on the

conspiracy charge," Rule 11(e)(1) was not violated. See United

States v. Johnson, 89 F.3d 778, 783 (11th Cir. 1996). 

Given this review of relevant case law, we sense a distinct

qualitative difference between statements found to require

vacation and the comments made here. In the first place, the

remarks of the court did not take place in the context of plea

negotiation discussions. The judge was speaking only to

counsel, in the context of the denial of a co-defendant's motion

for severance, and his comments were immediately followed by his
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reminder to counsel that he held no opinion on any plea

discussions or defendant's decision whether to plead guilty.

The judge did not threaten defendant with consequences if he did

not plead guilty, express a preference as to one penalty or

disposition, or attempt to shape the terms of the agreement, and

he reiterated his neutrality on any plea negotiations. Thus,

the coercion guarded against by Rule 11(e)(1) did not arise. We

think the Ninth Circuit said it best: "The rule against

judicial participation in plea bargaining protects the parties

against implicit or explicit pressure to settle criminal cases

on terms favored by the judge. It does not establish a series

of traps for imperfectly articulated oral remarks." United

States v. Frank, 36 F.3d 898, 903 (9th Cir. 1994). The court's

comments in the case at bar were of this nature. They were

impromptu, unemphatic, and unrepeated. To seize on such as

reversible error would, we conclude, raise the crossbar to an

unrealizable height.

Defendant's second contention is that he did not understand

the consequences of his plea. Defendant argues that the court

misled him to believe that he would be entitled to a three point

reduction for acceptance of responsibility, rendering his plea

invalid because he actually was entitled to only a two point

reduction due to the fact that he did not plead guilty in time
5Although not raised on appeal, the issue of whether

defendant was eligible for any acceptance of responsibility

reduction due to his entry of an Alford plea as opposed to an

unconditional guilty plea was raised at sentencing. Due to this

unresolved issue, the judge declined to make a determination as

to whether he was giving defendant: 1. both a two level

reduction for acceptance of responsibility under § 3E1.1 and a

two level enhancement under § 3B1.1(c) based on his role as a

manager of the personnel or assets of a criminal endeavor, or 2.

neither the reduction nor the enhancement. We review the issue

as if the court gave both the reduction and the enhancement.

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to spare the government the efforts of preparing for trial or to

allow the court to effectively allocate its resources. See

U.S.S.G. § 3E1.1.5 Defendant points specifically to the court's

sidebar comments as well as the following statements from the

plea colloquy: first, when speaking to the prosecutor while

defendant was in conference with his attorney, the court said,

"[a]ssume under guideline calculations a reduction for

acceptance of responsibility," and, second, when later asking

the defendant whether he'd been promised anything in exchange

for his guilty plea, the court noted, "one benefit [of pleading

guilty] is, if I think you've accepted your responsibility, the

guideline range is lower." 

We conclude that when the entirety of the plea colloquy is

reviewed, defendant's complaints hold no merit. The court

accurately depicted the sentencing possibilities: 

And under the guidelines I cannot go higher than the

top of the guidelines, up to life in prison, unless

there's something especially evil about you that's not
6Defendant was sentenced to 78 months on counts 1 through 4

(money laundering and conspiracy) and 71 months, to run

concurrently, on counts 9 and 11 (drug possession and

conspiracy).

Defendant insists that he believed the acceptance of

responsibility reduction would be applied to the 78 to 97 month

sentence, such that ultimately he would receive a sentence of

less than 78 months. Even if defendant's belief were

reasonable, a defendant's misunderstanding of the guideline

sentencing range does not require the court to allow his guilty

plea to be withdrawn. See United States v. De Alba Pagan, 33

F.3d 125, 127 (1st Cir. 1994).

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in those books. But equally, I can't go below the

bottom of the guidelines unless there's something

especially good about you that's not in those books,

and that's very rare.

So, I ask the government, not because I'm going to

follow what they tell me, but because they probably

want the most severe range of the people I will talk

to, to tell me what they think it will work out to be.

And they tell me you're looking at not less than 78

months nor more than 97 months in prison.

. . . .

Now, if it works out that way, it's very unlikely

then that I would be in a position to sentence you to

anything less than 78 months in prison.

Defendant ultimately was sentenced to seventy-eight months of

imprisonment.6

Defendant relies on United States v. Hernandez-Wilson, 186

F.3d 1 (1st Cir. 1999), and United States v. Gray, 63 F.3d 57

(1st Cir. 1995). In Gray, we vacated a guilty plea because,

when the defendant indicated that he did not understand the

maximum punishment, the court, in an effort to clarify, stated

that the maximum sentence would be ten years to life although in

fact the mandatory minimum sentence was ten years. See Gray, 63
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F.3d at 60-61. In Hernandez-Wilson, we allowed a defendant to

withdraw his guilty plea because "[h]e was told that he would be

eligible for a lighter sentence for which he was not eligible."

Hernandez-Wilson, 186 F.3d at 6.

In contrast, the court in this case did not provide

defendant with incorrect sentencing information at the plea

colloquy and in fact defendant was ultimately sentenced to

seventy-eight months, the lowest possible sentence in the range

cited by the judge. Admittedly the judge's sidebar reference to

the acceptance of responsibility credit envisioned a three point

reduction; nevertheless, it was an off-hand remark to

defendant's counsel at sidebar rather than any meaningful

portion of the plea colloquy and did not indicate to defendant

that he would receive a sentence lower than that which he did

receive. See, e.g., United States v. Raineri, 42 F.3d 36, 42

(1st Cir. 1994) (upholding guilty plea even though

misinformation given to the defendant because it did not lead

him to "expect a lesser penalty than he actually received").

The judge's subsequent and more important references to the

reduction at the plea colloquy did not reference the number of

points, and in fact once characterized the reduction as only a

possibility, and thus were not misleading. Moreover, they were

accompanied by an explanation that the guidelines calculation
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would be affected by post-pleading materials from the attorneys

and an understanding that the court would not be determining the

actual sentence until a later date.

Defendant also complains that the court neglected to inform

him that he faced a likely enhancement under U.S.S.G. §

2S1.1(b)(1) due to his knowledge that the funds he was

transmitting were drug proceeds. The court did not err by not

forewarning defendant of all possible sentencing enhancements he

might face. See United States v. De Alba Pagan, 33 F.3d 125, 127

(1st Cir. 1994) (holding that "the fact that a defendant

misapprehends the likely guideline sentencing range does not

constitute a fair and just reason for withdrawing a guilty

plea"). The court informed defendant that it was highly

unlikely that he would receive a sentence outside the applicable

guideline range and ultimately sentenced defendant to the lowest

penalty referenced as a possibility.

In conclusion, we find that the court's statements did not

affect defendant's substantial rights nor did they rise to the

level of a fundamental defect. Thus, defendant's plea was not

a product of coercion but instead was entered knowingly,

voluntarily, and intelligently.

III. Sentencing
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Defendant argues that the court erred by increasing his base

offense level by three due to his knowledge that the funds he

transmitted were the result of drug dealing. See U.S.S.G. §

2S1.1(b)(1) (calling for three level enhancement "[i]f the

defendant knew or believed that the funds were the proceeds of

an unlawful activity involving the manufacture, importation, or

distribution of narcotics or other controlled substances").

Defendant contends that because he entered an Alford plea to the

money laundering charges, the enhancement cannot be applied

because he did not admit to the requisite knowledge. He also

asserts that there was insufficient evidence to support the

court's factual findings.

The presentence report recommended a three level increase

under U.S.S.G. § 2S1.1 to which defendant did not object. Nor

did defendant object to this enhancement at sentencing. "We

have repeatedly stated in the sentencing context, as well as in

other areas, that issues not presented to the district court

will not be addressed for the first time on appeal." United

States v. Haggert, 980 F.2d 8, 10 (1st Cir. 1992). This rule is

relaxed only in "extreme cases." See id. at 11.

"It is well settled that during the sentencing proceedings,

a district court has broad discretion in determining the

information that may be received and considered regarding a
7Defendant's only objection to the factual description of

the offense conduct in the presentence report was to the use of

the word "managed."

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defendant." United States v. Pellerito, 918 F.2d 999, 1002 (1st

Cir. 1990); see 18 U.S.C. § 3577. Thus, it is not necessary

that defendant admit to the facts upon which an enhancement is

based.

As to the evidence supporting the court's finding, it is

more than sufficient. See United States v. Brum, 948 F.2d 817,

819 (1st Cir. 1991). The court was entitled to consider

evidence presented in the trial prior to defendant's guilty

plea, see United States v. Ruiz, 905 F.2d 499, 508 (1st Cir.

1990), as well as the facts recorded in the presentence report,

see United States v. Skrodzki, 9 F.3d 198, 202 (1st Cir. 1993),

such as that defendant was the principal contact with several of

the drug dealers using Best Video's services and that the

undercover officer represented the funds he wished to transfer

as funds for the purchase of drugs. In fact, the court

expressly adopted the facts set out in the presentence report,

facts which defendant did not substantively dispute. See United

States v. Lagasse, 87 F.3d 18, 20 (1st Cir. 1996) ("We accept

the facts found in the uncontested portions of the [PSR] . . .

.").7 The facts presented in the presentence report and at trial

were more than sufficient to support the court's finding that
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defendant had knowledge that the funds were the fruit of drug

dealings. See United States v. Knecht, 55 F.3d 54, 57 (2d Cir.

1995) (enhancement valid even when the only reason defendant had

to form the belief was a statement by an undercover agent in a

sting operation).

Thus, this is far from the "extreme case" in which the

raise-or-waive rule should be relaxed.

IV. Ineffective Assistance of Counsel

Finally, defendant contends that his trial counsel provided

him with ineffective assistance in violation of his Sixth

Amendment right. As we have often held, "fact-specific claims

of ineffective assistance cannot make their debut on direct

review of criminal convictions, but, rather, must originally be

presented to, and acted upon by, the trial court." United

States v. Mala, 7 F.3d 1058, 1063 (1st Cir. 1993) (citing

cases). We have allowed exceptions "only when the critical

facts are not in dispute and the record is sufficiently

developed to allow reasoned consideration of the claim." Id.

Defendant's claims revolve around his trial counsel's

recommendations with regard to pleading and sentencing,

involving facts not well developed nor necessarily free from

dispute. Moreover, defendant does not argue that his claim is

one that can be effectively evaluated for the first time on
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appeal. In short, it is a claim that must be brought first

before the district court via a request for post-conviction

relief.

V. Conclusion

We conclude that the court's statements did not affect

defendant's substantial rights nor did they constitute a

fundamental defect and that defendant's guilty plea was knowing,

voluntary, and intelligent. Further, the court did not err in

enhancing defendant's sentence under U.S.S.G. § 2S1.1(b)(1).

Finally, defendant's ineffective assistance claim is dismissed

without prejudice.

Affirmed.