217 F.3d 15 (1st Cir.

2000)

UNITED STATES OF AMERICA, APPELLEE,

v.
ANTONIO BIERD, DEFENDANT, APPELLANT.
No. 98-2178

United States Court of Appeals For the First Circuit

Heard May 9, 2000
Decided June 28, 2000

[Copyrighted Material Omitted]

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.
Before Torruella, Chief Judge, Coffin, Senior Circuit Judge, and Stahl,
Circuit Judge.
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.
3

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
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 - - 9

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

10

Court: Well, if that happens, it happens. I have nothing to say about it.

11

The next day, defendant entered his Alford and unconditional guilty pleas and
he was subsequently sentenced.

12

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.

13

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

14

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.

15

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
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).

16

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, 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."
17

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.

18

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 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).

19

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.

20

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 a more stringent plea agreement than that proposed. See
United States v. Miles, 10 F.3d 1135, 1138-40 (5th Cir. 1993).

21

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:

22

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.

23

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 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).
24

On the other hand, in Blackmon v. Wainwright, 608 F.2d 183 (5th Cir. 1979),
the court held that a trial judge's "off-the-cuff" 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).

25

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 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.

26

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 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."
27

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:

28

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 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.

29

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.

30

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.

31

Defendant ultimately was sentenced to seventy-eight months of imprisonment.6

32

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 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.

33

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 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.
34

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.

35

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

36

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.

37

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.

38

"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 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.

39

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
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).

40

Thus, this is far from the "extreme case" in which the raise-or-waive rule
should be relaxed.
IV. Ineffective Assistance of Counsel

41

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.
42

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 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

43

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.

44

Affirmed.

NOTES:
1

When 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.

In 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.

We also evaluate "(1) the plausibility of the reasons prompting the requested
change of plea; (2) the timing of the 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.
4

In 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.

Although 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.

Defendant 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).

Defendant's only objection to the factual description of the offense conduct in

the presentence report was to the use of the word "managed."