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. S. v. M acPher s on

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)

- - - - - - - - - - - - - - - - - UNITED STATES OF AMERICA,

Appellee,

v. CARLOS MACPHERSON,

Defendant-Appellant.

- - - - - - - - - - - - - - - - - Before: NEWMAN, CALABRESI, and KATZMANN, Circuit Judges. Appeal from the April 15, 2 0 0 8 , 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., SusanCorkery, Licha M . Nyiendo, Asst. U.S. Attys., Brooklyn, New Y o rk, N.Y., on the brief), for Appellee.
PER CURIAM: This criminal appeal challenges a sentence for a n arcotics violation on the ground that the Gov e r n m e nt 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 Ea s t e r n 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
Ma c P h e r s o n a n d h i s c o - d e f e n d a n t s w e r e c h a r g e d i n a t h r e e count indictmen t 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 g r a m s o r more of heroin and five k i l o g r a ms or more of cocaine, in violation of 21 U.S.C. §§ 963, 9 6 0(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-3-

of a likely Guidelines sentencing range. The agreement stated, in pertinent part:

2. . . . Th e O f f i c e 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 sen t ence. The Office estimates the likely adjusted offense level under the Guidelines to be level 32 [calculated from base off e n se level 34, see U.S.S.G. § 2D1.1(c)(3 ) , l e ss 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, 2 0 0 7 , 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. T h i s level carries a range of imprisonment of 108 to 135 m o nths, 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 s h o u l d 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 Cour t . If the Guidelines offense level advocated by the Office, or determined by the Probation Department or the Court, is differen t f rom 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 c o ncerning where within the-4- Guidelines range determined by the Court the sentence should fall; and c. Make no motion for an up w a r d 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 stip u l a t ed 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 t h e g uidelines will be or whether there will be grounds to depart from them or whether the Court will impose a non-guideline senten c e , do you understand that? The defendant answered, “Yes.” In response to the Court’s inquiry, the p r o s e c utor 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-5-

as c e r tained 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 heroi n ” a nd “5 kilograms or more of a substance containing cocaine.” The d efendant explicitly acknowledged repeatedly traveling to Peru to make arr a n g ements 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 d e f e ndant conspired to import and distribute fifteen kilograms of co c a i n e 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., m anaging criminal activity involving more than five conspirators. As a result, the PSR found appellant’s total offense level to be 37, 6 levels high e r 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-6-

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
determ i n e dt h a t a n o n - G u i d e l i n e s s e n t e n c e w a s n o t a p p r o p r i a t e . T he
Cou r t a l s o f ound that the defendant had not been forthright in his acceptance of responsibility. The Court f o u n d that the defendant’s
offense level was 37 with a sentencing range of 210 to 262 months and impo s e d 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 ) w h ether 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 . 2 0 0 7 ) ; United States v. Lawlor, 168 F.3d 633, 636 (2d Cir. 1999), the Supreme Court-7-

has more recently ruled that such claims are to be reviewed only for plain error in the absence of objection in the t r i al 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 proceedi n g s , resulting in a miscarriage of justice. See United States v. Zvi, 168 F.3d 49, 58 (2d Cir. 1999). (2) Applying plain error review.
F o r t h e f i r s t t i m e o n a p p e a l , M a c P h e r s o n c o n t e n d s t h a t 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
tha t his sentence should be calculated based on a drug type and quantity of fifteen kilograms or mor e 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 co n t e n t ion 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.-8-

Habbas, 527 F.3d 266 (2d Cir. 2008). Palladino r uled that the plea could be withdrawn after the prosecutor advocate d 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 go v e r nment from deviating from a Pimentel estimate, absent newly di s covered facts.” Id. at 272. In view of these conflicting outcomes concerning plea withdrawal in two cases where the prosecutor advocated a sentencin g r ange 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 sen t e n c e b a sed on the seven kilograms of heroin constitute plain error just because the plea agreement stated that the defendant “stipula tes that his sentence
should b e c a l culated based on a drug type and quantity of fifteen kilograms or more of a sub s t a n c e containing cocaine.” Initially, we note that, whereas typical contract stipulations state that the parties-9-

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 th e plea colloquy put the
defendant on notice that the Pimentel estimate was not binding on the prosecutor an d 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-co u n ted certain factors by sentencing him at the hi g h 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
fac t o r s w ere that MacPherson had trafficked in heroin and cocaine in substantial quantitie s , h e was an organizer and a supervisor and had recruited couriers, and he had engaged in narcotics offenses prior to the charged crime.
In i t i a l l y, we note that there is no authority that prevents a

s e n t e n c i n g j u d g e f r o m u s i n g f a c t s o f t h e o f f e n s e c o n d u c t both to determine the applicable Guidelines range and to select a sen t e n ce 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 t h e o r ganization 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-10-

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 tr ying 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 withdrawh i s g uilty 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. Pa l l adino, 347 F.3d 29 (2d Cir. 2003), and United States v. Habbas, 527 F.3d 266 (2d Cir. 2006), this Court’s two most

r e c e nt 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 a g r e ement 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 ba s e d o n a socalled Piment e l e s t imate. See United States v. Pimentel, 932 F.2d 1029, 1034 (2d Cir. 1991). Notwithstanding these differences, the d e cisions are similar in

sever a l r e s pects. 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 s t a t e m e nt 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-2-

similarit i e s , w e ruled that denying withdrawal of the plea was error in Palladino and was not error in Habbas. Palladino found t h e a greement breached because “[i]t was . . . logical for defendant to beli eve 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 i nformation known to
the Of f i c e a t t h i s t i m e , ” a p h r a s e t h a t p r e c e d e dt h e G o v e r n m e n t’s Guidelines range estimate. Id. at 31.
Ther e c a n 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 attenti on of the sentencing judge. See id. at 33. Third, and most important, the Court explicitly re l i e d o n the phrase in stating its rationale: In the circumstances presented in this case, we believe that defendant h a d a reasonable expectation that the Government would not press the Court for an enhanced offense level in the absence of new inf o r m a t i on. 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 pl e a ] . ” . . . It was thus logical for defendant to believe that the estimate, and the Government’s stance at the se n t e n c i ng 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:-3- The problem in Palladino was not th at those words appeared in the Pimentel esti mate, 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 g o v e r n m ent’s change of position. Based on our reading of Palladino, we v e r y m u ch doubt that the result of that case wou l d h a v e c h a n g e d i f , a l l e l s e r e m a i n i n g t h e s a m e , those words had not appeared in the Pimentel estimate. Habbas, 527 F.3d at 272 n.1. I agree with Habb a s on this point.
Whether or no t 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 bin d i n g o n 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 p l e a a greement was violated when the Government
advocated a n e n h a ncement based on information that had been known at the time of the plea. In light of P a l l a d i no, a defendant in Habbas, named Rahman,
contended that whenever the Government makes a Pimentel estimate, the plea agreement prohibits the Government from devi ating from the-4-

estimate i n t h e 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 “establ i shed a broad rule, categorically prohibiting the government from deviating from a Pimentel estimat e, absent newly discovered facts.” See id. at 272. The plea agreement in the pending case does n o t have the “known
to t h e O f f i c e ” l a n g u a g e , w h i c h P a l l a d i n o d e e m e d c r i t i c a l , b u t which Habbas deemed inconsequential. On the other hand, the plea agreement does have the “not binding” and “adv o c a t e [ ]” language, which Habbas deemed critical, but which Palladino deemed inconsequential. Palladino and Habbas are problematic, not only for the ir inconsistency but also for the u n c e r t a i n ty they risk for the use of Pimentel estimates. I agree with Habbas that there s hould not be a bright-line rule permitting a plea to be withdrawn when e v e r the
Government advocates a sentence above the plea agreement estimate. If we start inquiring as to what the Go v e r n m e n t k new at the time of the plea agreement, we ope n 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?-5-

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 cle a r , b ut 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 r e flected in a Pimentel estimate, we would open up a potentially broad inquiry of uncertain limits. I think a f a r b e t ter approach is to uphold all plea agreements with Pime n t e l 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 th e e s t i mate and the district judge ascertains at the plea colloquy that (1) the defendant understands that the estimate is not binding an d (2) if the estimate is wrong, the
defendant will not be permitted to withdraw his plea. That would leave Pimentel letters where they were init i a l ly intended to be: only estimates and not a basis for limitin g t he Government’s sentencing advocacy nor a basis for withdrawing a plea. In this case, the plea agreement explicitly stated: The Guidelines estimate put fort h in paragraph 2 is not bind i n g on the Office, the Probation Department or the Court . If the Guidelines offense level advocated by the Offi c e , or determined by the Probation Department or the Cour t, 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-6-

advo c a t e a t 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, t h e p l ea colloquy included the following: THE COURT: The bottom line is that u n t i l the date of sentencing when we get a pre s e n t e n ce report, as I said before, and I hear from you, your l a w y e r and from the Government, we will not know wit h a ny certainty what the guidelines will be or whether there w i l l b e grounds to depart from them or whether th e C o u r t will impose a nonguideline sentence, do you understand that? THE DEFENDANT: Yes, Your Honor. THE COURT: Do you understand t h a t 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 w r o n g , 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, t h e r e w ould not be certainty as to what the applicable guideline would be, (b) the es t i m ate in the plea

a g r eement was not binding on the Government, and (c) if the estimate was incorrect, the plea could not be withdrawn. A plea colloquy can be e x a m ined to determine a defendant’s
und e r s t a n d i ng 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. Wool l e y , 1 2 3 F.3d 627, 632 (7th Cir. 1997). The colloquy in this case removes any bas is for-7-

permitting the defendant to wit h d r a w his plea simply because, at the time of t h e p l e a 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 advers e 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 len ient sentence, and if he does

n o t g e t o n e , h e t h e n a p p e a l s o n t h e g r o u n d t h a t h e s h o u l d 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.