08-1829-cr (CON))

U.S. v. MacPherson 

UNITED STATES COURT OF APPEALS

FOR THE SECOND CIRCUIT

August Term 2009

Submitted: October 19, 2009 Decided: December 30, 2009

Docket No. 08-1829-cr (CON)

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UNITED STATES OF AMERICA,

Appellee,

 v.

CARLOS MACPHERSON,

Defendant-Appellant.

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Before: NEWMAN, CALABRESI, and KATZMANN, Circuit Judges.

Appeal from the April 15, 2008, judgment of the United States

District Court for the Eastern District of New York (Dora L. Irizarry,

District Judge), sentencing the defendant to 262 months’ imprisonment

upon his plea of guilty to narcotics offenses. The defendant contends

that he should be permitted to withdraw his plea because at sentencing

the prosecutor advocated a Guidelines sentencing range higher than the

range estimated in the plea bargain. Judge Newman concurs with a

separate opinion.

Affirmed.

Todd M. Merer, New York, N.Y., for

Defendant-Appellant.

Benton J. Campbell, U.S. Atty., Susan
Corkery, Licha M. Nyiendo, Asst.

U.S. Attys., Brooklyn, New York,

N.Y., on the brief), for Appellee.

PER CURIAM:

This criminal appeal challenges a sentence for a narcotics

violation on the ground that the Government violated the plea

agreement by recommending a sentence higher than the range estimated

to be applicable at the time of the plea. The appeal also challenges

the reasonableness of the sentence, which included 262 months’

imprisonment. Carlos MacPherson appeals from the April 15, 2008,

judgment of the District Court for the Eastern District of New York

(Dora L. Irizarry, District Judge). Applying plain error review to

the challenge to the plea agreement, see Puckett v. United States, 129

S. Ct. 1423, 1428-33 (2009), we conclude that, if any error occurred

with respect to the plea agreement, it was not plain error, and that

the sentence survives review for reasonableness. We therefore affirm.

Background

MacPherson and his co-defendants were charged in a three count

indictment with various narcotics offenses. Pursuant to a plea

agreement, MacPherson pled guilty to one count, which charged him with

conspiring to import into the United States 100 grams or more of

heroin and five kilograms or more of cocaine, in violation of 21

U.S.C. §§ 963, 960(a)(1), 960(b)(2)(A), and 960(b)(1)(B)(ii). In

conformity with United States v. Pimentel, 932 F.2d 1029, 1034 (2d

Cir. 1991), the Government included in the plea agreement its estimate
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of a likely Guidelines sentencing range. The agreement stated, in

pertinent part:

2. . . . The Office will advise the Court and the

Probation Department of information relevant to sentencing,

including criminal activity engaged in by the defendant, and

such information may be used by the Court in determining the

defendant’s sentence. The Office estimates the likely

adjusted offense level under the Guidelines to be level 32

[calculated from base offense level 34, see U.S.S.G.

§ 2D1.1(c)(3), less 2 levels for acceptance of

responsibility, see id. § 3E1.1(a)]. This level carries a

range of imprisonment of 121 to 151 months [in Criminal

History Category I]. If the defendant pleads guilty on or

before June 20, 2007, the government will move the Court,

pursuant to U.S.S.G. § 3E1.1.(b), for an additional onelevel reduction, resulting in an adjusted offense level of

31. This level carries a range of imprisonment of 108 to

135 months, assuming that the defendant will be sentenced

within Criminal History Category I. Because the applicable

statutory mandatory minimum sentence is ten years[‘]

imprisonment, the applicable Guidelines range is expected to

be 120 to 135 months. The defendant stipulates that his

sentence should be calculated based on a drug type and

quantity of fifteen kilograms or more of a substance

containing cocaine and waives any right to a jury trial in

connection with such issue.

3. The Guidelines estimate set forth in paragraph 2 is

not binding on the Office, the Probation Department or the

Court. If the Guidelines offense level advocated by the

Office, or determined by the Probation Department or the

Court, is different from the estimate, the defendant will

not be entitled to withdraw the plea.

. . .

5. The Office agrees that:

. . .

based upon information now known to the Office, it will

b. take no position concerning where within the
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Guidelines range determined by the Court the sentence should

fall; and

c. Make no motion for an upward departure under

the Sentencing Guidelines.

If information relevant to sentencing, as determined by the

Office, becomes known to the Office after the date of this

agreement, the Office will not be bound by paragraphs 5(b)

and 5(c).

At the plea hearing the District Court, after ascertaining that

the defendant understood the rights he was giving up by pleading

guilty, stated:

Let me just also remind you that by entering into this

[plea] agreement you have stipulated that your sentence

should be calculated based on the drug type and quantity of

15 kilograms or more of a substance containing cocaine and

that you have waived any right to a jury trial in connection

with any such issue, do you understand that?

The defendant answered, “Yes.”

The Court then discussed the Guidelines and stated:

The bottom line is that until the date of sentencing when we

get a presentence report, as I said before, and I hear from

you, your lawyer and from the government, we will not know

with any certainty what the guidelines will be or whether

there will be grounds to depart from them or whether the

Court will impose a non-guideline sentence, do you

understand that?

The defendant answered, “Yes.”

In response to the Court’s inquiry, the prosecutor stated that

“the government estimates that the defendant would fall within

adjusted offense level 31” with a sentencing range, because of the ten

year mandatory minimum, of 120 to 135 months. The Court then
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ascertained that the defendant understood that “these are all

estimates that are not binding on the government, Probation or the

Court” and that “if this estimate is wrong, that you will not be

permitted to withdraw your plea of guilty.”

The Court then turned to the specifics of Count One, reading it

verbatim to the defendant, including the references to importing “100

grams or more of a substance containing heroin” and “5 kilograms or

more of a substance containing cocaine.” The defendant explicitly

acknowledged repeatedly traveling to Peru to make arrangements to

purchase heroin and meeting a courier at John F. Kennedy Airport who

was carrying ten kilograms of cocaine.

The Court accepted the guilty plea to Count One. 

The Presentence Report (“PSR”) determined that the defendant

conspired to import and distribute fifteen kilograms of cocaine and

seven kilograms of heroin. The PSR recommended an upward adjustment

of 4 levels for the role that the defendant played in the offense,

i.e., managing criminal activity involving more than five

conspirators. As a result, the PSR found appellant’s total offense

level to be 37, 6 levels higher than the estimate of 31 in the plea

agreement. The sentencing range at offense level 37 in Criminal

History Category I is 210 to 262 months. 

At sentencing, the defendant objected to the four level

enhancement for his role in the offense and the inclusion of the seven
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kilograms of heroin in the determination of his offense level. The

Defendant did not object on the basis of the inconsistency between the

estimate of the Guidelines sentencing range in the plea agreement and

the PSR, nor did he seek to withdraw his guilty plea. The Government

advocated a sentence based on seven kilograms of heroin, in addition

to the cocaine, and a role adjustment. The District Court overruled

the defendant’s objections, reviewed the section 3553(a) factors, and

determined that a non-Guidelines sentence was not appropriate. The

Court also found that the defendant had not been forthright in his

acceptance of responsibility. The Court found that the defendant’s

offense level was 37 with a sentencing range of 210 to 262 months and

imposed a sentence of 262 months’ imprisonment, five years of

supervised release, and a $100 special assessment.

Discussion

There are two issues for review: (1) whether the Government

violated the plea agreement and (2) whether appellant’s sentence at

the high end of the applicable Guidelines range was appropriate.

I. Claimed Violation of the Plea Agreement

(1) Standard of review. Although we have previously ruled that

a defendant need not object in the trial court in order to preserve

for appeal a claim that a plea agreement has been violated, see, e.g.,

United States v. Griffin, 510 F.3d 354, 360 (2d Cir. 2007); United

States v. Lawlor, 168 F.3d 633, 636 (2d Cir. 1999), the Supreme Court
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has more recently ruled that such claims are to be reviewed only for

plain error in the absence of objection in the trial court. See

Puckett, 129 S. Ct. at 1428-33. To prevail on plain error review, an

appellant must show that (1) there is error, (2) it is plain, (3) it

affects a substantial right, and (4) it seriously affects the fairness

of the judicial proceedings, resulting in a miscarriage of justice.

See United States v. Zvi, 168 F.3d 49, 58 (2d Cir. 1999).

(2) Applying plain error review. 

For the first time on appeal, MacPherson contends that his

sentence violated the plea agreement. His claim is based not only on

the Government’s advocacy of a sentence based on the seven kilograms

of heroin that were not included in the Pimentel estimate, but also on

the sentence in the plea agreement in which the defendant “stipulates

that his sentence should be calculated based on a drug type and

quantity of fifteen kilograms or more of a substance containing

cocaine.” He contends that the Government’s advocacy that his

sentence should be based on the seven kilograms of heroin, which were

known to the Government at the time of the plea agreement, shows that

the Government’s estimate was in bad faith and justifies an

opportunity to withdraw his plea. Whether this contention survives

plain error review requires some consideration of two recent decisions

concerning sentences that exceed Government Pimentel estimates, United

States v. Palladino, 347 F.3d 29 (2d Cir. 2003), and United States v.
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Habbas, 527 F.3d 266 (2d Cir. 2008).

Palladino ruled that the plea could be withdrawn after the

prosecutor advocated a higher sentencing range than the range

estimated in the plea agreement. However, in similar circumstances,

Habbas ruled that the plea could not be withdrawn, stating:

[W]e reject [the defendant’s] argument that the government

violated his rights under the plea agreement by advocating

a higher Guidelines level than it had estimated in the plea

agreement.

Habbas, 527 F.3d at 270. In addition, Habbas explicitly rejected the

claim that Palladino “established a broad rule, categorically

prohibiting the government from deviating from a Pimentel estimate,

absent newly discovered facts.” Id. at 272. In view of these

conflicting outcomes concerning plea withdrawal in two cases where the

prosecutor advocated a sentencing range higher than the range

estimated in the plea agreement, the prosecutor’s similar conduct in

the pending case cannot have precipitated plain error, if any error at

all.

 Nor does the prosecutor’s advocacy of a sentence based on the

seven kilograms of heroin constitute plain error just because the plea

agreement stated that the defendant “stipulates that his sentence

should be calculated based on a drug type and quantity of fifteen

kilograms or more of a substance containing cocaine.” Initially, we

note that, whereas typical contract stipulations state that the parties
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stipulate to some agreed upon terms, the agreement in this case states

only that the defendant stipulates to a sentence based on the cocaine

quantity. In any event, the agreement and the plea colloquy put the

defendant on notice that the Pimentel estimate was not binding on the

prosecutor and that if the estimate was wrong, the plea could not be

withdrawn. In such circumstances, there was no plain error.

II. Challenge to the Sentence

The Appellant contends that the District Court double-counted

certain factors by sentencing him at the high end of the guideline

range based on the same factors that provided the basis for the Court’s

finding of the applicable Guidelines range in the first place. These

factors were that MacPherson had trafficked in heroin and cocaine in

substantial quantities, he was an organizer and a supervisor and had

recruited couriers, and he had engaged in narcotics offenses prior to

the charged crime.

Initially, we note that there is no authority that prevents a

sentencing judge from using facts of the offense conduct both to

determine the applicable Guidelines range and to select a sentence

within that range. In any event, the District Court did not limit its

articulation of sentencing reasons to facts that determined the

sentencing range. The Court explained that MacPherson created “his own

drug organization,” got his father involved in the organization as a

courier, “preyed on some of [his] co-defendants when they were facing

dire family situations and [] enticed them into helping [him] to bring
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drugs into this country.” The Court also noted that when one of

MacPherson’s co-defendants “tried to extricate herself, and in fact she

did extricate herself, [appellant] still came after her trying to

convince her to get back involved.” Sentencing at the high end of the

applicable range was not unreasonable.

 Conclusion

The judgment of the District Court is affirmed.
U.S.A. v. MacPherson

Docket No. 08-1829-cr (CON)

JON O. NEWMAN, Circuit Judge, concurring:

I agree that MacPherson is not entitled to withdraw his guilty

plea because not only is there no plain error, as the Court holds,

there is no error at all. I add these additional views to explain why

this is so, a discussion that endeavors to resolve the tension between

United States v. Palladino, 347 F.3d 29 (2d Cir. 2003), and United

States v. Habbas, 527 F.3d 266 (2d Cir. 2006), this Court’s two most

recent decisions on plea withdrawal claims based on a prosecutor’s

advocacy at sentencing of a Sentencing Guidelines range higher than the

range estimated in a plea bargain. These decisions differ not only in

their outcomes (plea agreement violated in Palladino; plea agreement

not violated in Habbas), but critically in their rationale as to what

circumstances establish a breach of a plea agreement based on a socalled Pimentel estimate. See United States v. Pimentel, 932 F.2d

1029, 1034 (2d Cir. 1991).

Notwithstanding these differences, the decisions are similar in

several respects. In both Palladino and Habbas, the plea agreement

included an estimate by the prosecutor as to the applicable sentencing

range under the Sentencing Guidelines. Both agreements also included

a statement that the estimate was based on information known to the

Government at the time of the plea agreement. And in both cases, the

prosecutor contended at sentencing that the applicable Guidelines

sentencing range was higher than originally estimated. Despite these
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similarities, we ruled that denying withdrawal of the plea was error

in Palladino and was not error in Habbas.

Palladino found the agreement breached because “[i]t was . . .

logical for defendant to believe that the estimate, and the

Government’s stance at the sentencing hearing, would not be altered in

the absence of new information . . . .” 347 F.3d at 34. The basis for

that belief was said to be the phrase “based on information known to

the Office at this time,” a phrase that preceded the Government’s

Guidelines range estimate. Id. at 31.

There can be no doubt that Pallidino considered this phrase

critical. First, it was italicized when quoted. See id. Second, the

Court noted as “a curious fact” that this phrase was not brought to the

attention of the sentencing judge. See id. at 33. Third, and most

important, the Court explicitly relied on the phrase in stating its

rationale:

In the circumstances presented in this case, we believe

that defendant had a reasonable expectation that the

Government would not press the Court for an enhanced offense

level in the absence of new information. The language of

the agreement specifically stated that the Government’s

estimate was “based on information known to the [Government]

at [the time of the plea].” . . . It was thus logical for

defendant to believe that the estimate, and the Government’s

stance at the sentencing hearing, would not be altered in

the absence of new information . . . .

Id. at 34.

However, Habbas views the phrase “known to the Government” as

of little, if any, consequence:
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The problem in Palladino was not that those words appeared

in the Pimentel estimate, but rather the combination of

passages of the plea agreement conferring assurance that the

government would not advocate for a sentence higher than the

estimate, with the aura of unfair dealing that underlay the

government’s change of position. Based on our reading of

Palladino, we very much doubt that the result of that case

would have changed if, all else remaining the same, those

words had not appeared in the Pimentel estimate.

Habbas, 527 F.3d at 272 n.1. I agree with Habbas on this point.

Whether or not the Government says that its estimate is based on

information “known to the Government at this time,” the estimate could

only be based on such information. It could not be based on what the

Government does not know at that time!

The decisions also differ in the significance they attach to the

phrases in both plea agreements stating that (a) the estimate “is not

binding on the [United States Attorney’s] Office,” and (b) if the

Guidelines level “advocated by the [United States Attorney’s] Office”

is “different from the estimate,” the defendant could not withdraw the

plea. Habbas says that these statements “warned in several different

ways that the government was likely to advocate for a higher sentence.”

Id. at 270-71. Palladino accorded no significance to these statements

and ruled that the plea agreement was violated when the Government

advocated an enhancement based on information that had been known at

the time of the plea.

In light of Palladino, a defendant in Habbas, named Rahman,

contended that whenever the Government makes a Pimentel estimate, the

plea agreement prohibits the Government from deviating from the
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estimate in the absence of new evidence. However, Habbas explicitly

rejected that interpretation:

[W]e reject Rahman’s argument that the government violated

his rights under the plea agreement by advocating a higher

Guidelines level than it had estimated in the plea

agreement.

Habbas, 527 F.3d at 270. In addition, Habbas explicitly rejected the

claim that Palladino “established a broad rule, categorically

prohibiting the government from deviating from a Pimentel estimate,

absent newly discovered facts.” See id. at 272.

The plea agreement in the pending case does not have the “known

to the Office” language, which Palladino deemed critical, but which

Habbas deemed inconsequential. On the other hand, the plea agreement

does have the “not binding” and “advocate[]” language, which Habbas

deemed critical, but which Palladino deemed inconsequential.

Palladino and Habbas are problematic, not only for their

inconsistency but also for the uncertainty they risk for the use of

Pimentel estimates. I agree with Habbas that there should not be a

bright-line rule permitting a plea to be withdrawn whenever the

Government advocates a sentence above the plea agreement estimate. If

we start inquiring as to what the Government knew at the time of the

plea agreement, we open up a difficult area. Would the Government

“know” of more offense conduct at the time of the plea agreement only

if the evidence was in the office, or if an agent had told a prosecutor

about it, or if a confidential informant had told the agent about it?
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How reliable would the information have to be to be “known” to the

Government for purposes of making a Pimentel estimate binding? In the

pending case, the Government’s knowledge of the heroin at the time of

the plea agreement is clear, but if we were to make withdrawal of a

plea available whenever the Government can be said to have “knowledge”

of more offense conduct than is reflected in a Pimentel estimate, we

would open up a potentially broad inquiry of uncertain limits.

I think a far better approach is to uphold all plea agreements

with Pimentel estimates, regardless of whether the Government at

sentencing advocates a higher Guidelines range (even one based on

previously known facts), as long as the agreement makes clear that the

Government is not bound by the estimate and the district judge

ascertains at the plea colloquy that (1) the defendant understands that

the estimate is not binding and (2) if the estimate is wrong, the

defendant will not be permitted to withdraw his plea. That would leave

Pimentel letters where they were initially intended to be: only

estimates and not a basis for limiting the Government’s sentencing

advocacy nor a basis for withdrawing a plea.

In this case, the plea agreement explicitly stated:

The Guidelines estimate put forth in paragraph 2 is not

binding on the Office, the Probation Department or the

Court. If the Guidelines offense level advocated by the

Office, or determined by the Probation Department or the

Court, is different from the estimate, the defendant will

not be entitled to withdraw his plea.

Plea Agreement, ¶ 3. This language makes clear that the Government may
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advocate at sentencing a guideline higher than the estimate. The

agreement in Habbas contained identical language, see Habbas, 527 F.3d

at 270, and the Habbas opinion relied on it, see id.

More important, in our case, the plea colloquy included the

following:

THE COURT: The bottom line is that until the date of

sentencing when we get a presentence report, as I said

before, and I hear from you, your lawyer and from the

Government, we will not know with any certainty what the

guidelines will be or whether there will be grounds to

depart from them or whether the Court will impose a nonguideline sentence, do you understand that?

THE DEFENDANT: Yes, Your Honor.

THE COURT: Do you understand that these are all

estimates that are not binding on the government, Probation

or the Court?

THE DEFENDANT: Yes, Your Honor.

THE COURT: Do you also understand that if this estimate

is wrong, that you will not be permitted to withdraw your

plea of guilty?

THE DEFENDANT: Yes, Your Honor.

Thus, the Court’s colloquy informed MacPherson that (a) until the

Court heard from the Government, there would not be certainty as to

what the applicable guideline would be, (b) the estimate in the plea

agreement was not binding on the Government, and (c) if the estimate

was incorrect, the plea could not be withdrawn.

A plea colloquy can be examined to determine a defendant’s

understanding of a plea agreement. See United States v. Woods, 581

F.3d 531, 534 (7th Cir. 2009); United States v. Azure, 571 F.3d 769,

773-74 (8th Cir. 2009); United States v. Woolley, 123 F.3d 627, 632

(7th Cir. 1997). The colloquy in this case removes any basis for
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permitting the defendant to withdraw his plea simply because, at the

time of the plea agreement, the Government knew of facts that would

have justified a higher estimate.

If we permit withdrawal of a plea in cases such as this, we risk

two adverse consequences. First, the Government will likely stop

making Pimentel estimates. These estimates are not required, and will

not be continued if they serve as a frequent basis for post-sentencing

plea withdrawals. Second, the defendant gets two bites at the apple:

he first argues at sentencing for a lenient sentence, and if he does

not get one, he then appeals on the ground that he should be allowed

to withdraw his plea. A properly worded plea agreement and a clear

plea colloquy concerning that agreement, both of which were present in

the pending case, should avoid both consequences.