13-3601-pr 

Jeffrey Alnutt v. United States 

UNITED STATES COURT OF APPEALS 

FOR THE SECOND CIRCUIT 

SUMMARY ORDER 

Rulings by summary order do not have precedential effect. Citation to a summary order filed 

on or after January 1, 2007, is permitted and is governed by Federal Rule of Appellate 

Procedure 32.1 and this Court’s Local Rule 32.1.1. When citing a summary order in a 

document filed with this Court, a party must cite either the Federal Appendix or an 

electronic database (with the notation “summary order”). A party citing a summary order 

must serve a copy of it on any party not represented by counsel. 

At a stated term of the United States Court of Appeals for the Second Circuit, held at 

the Thurgood Marshall United States Courthouse, 40 Foley Square, in the City of New York, 

on the 18th day of December, two thousand fourteen. 

PRESENT: JOSÉ A. CABRANES, 

RICHARD C. WESLEY, 

 PETER W. HALL, 

 Circuit Judges. 

 

JEFFREY E. ALNUTT, 

Petitioner-Appellant, 

v. 

 No. 13-3601-pr 

UNITED STATES OF AMERICA, 

Respondent-Appellee. 

 

FOR PETITIONER-APPELLANT: Jeffrey E. Alnutt, pro se, Attica NY. 

FOR APPELLEE: Grant C. Jaquith, Paul D. Silver, Assistant 

United States Attorneys, for Richard S. 

Hartunian, United States Attorney for the 

Northern District of New York, Albany, NY. 

Appeal from a September 6, 2013 order of the United States District Court for the Northern 

District of New York (Frederick J. Scullin, Jr., Judge). 
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UPON DUE CONSIDERATION WHEREOF, IT IS HEREBY ORDERED, 

ADJUDGED, AND DECREED that the order of the District Court is AFFIRMED. 

Appellant Jeffrey Alnutt, proceeding pro se, appeals from the district court’s September 6, 

2013 order denying him relief pursuant to 28 U.S.C. § 2255. On January 29, 2014, we granted a 

certificate of appealability on the following two issues: whether Alnutt received ineffective assistance 

of trial counsel when his attorney failed to object at sentencing to the calculations contained in the 

Presentence Report regarding Alnutt’s (1) base offense level, to the extent that Appellant’s 

conviction for criminal sale of a controlled substance in the third degree could have been based on a 

mere offer to sell, and (2) criminal history category, to the extent that the Presentence Report 

indicated that Alnutt had a separate criminal conviction in April 1988 for criminal possession of a 

controlled substance in the third degree (“drug possession conviction”). We decline to address any 

other claims raised in Alnutt’s brief. See Soto v. United States, 185 F.3d 48, 53 (2d Cir. 1999) (declining 

to address any claim other than the one in the COA). We also decline to consider the Government’s 

argument, raised for the first time on appeal, that the collateral attack waiver in Alnutt’s plea 

agreement bars him from raising his ineffective assistance claims. See Tallent v. United States, 567 F. 

App’x 343, 346-47 (6th Cir. 2014) (forfeiting defense of collateral attack waiver if not raised below); 

cf. United States v. Cannady, 126 F.3d 352, 359 (2d Cir. 1997) (forfeiting procedural default defense). 

The Government moves to introduce evidence of Alnutt’s drug possession conviction, which it did 

not introduce during the district court proceedings. We assume the parties’ familiarity with the 

underlying facts and the procedural history of the case. 

 In evaluating the denial of relief under § 2255, we review findings of fact for clear error and 

conclusions of law de novo. Scanio v. United States, 37 F.3d 858, 859 (2d Cir. 1994). “The question of 

whether a defendant’s lawyer’s representation violates the Sixth Amendment right to effective 

assistance of counsel is a mixed question of law and fact that is reviewed de novo.” United States v. 

Blau, 159 F.3d 68, 74 (2d Cir. 1998). 

 The standards governing claims of ineffective assistance of counsel are well established. The 

defendant must prove both that (1) counsel’s performance “fell below an objective standard of 

reasonableness” and (2) counsel’s deficient performance prejudiced the defendant, resulting in an 

unreliable or fundamentally unfair outcome in the proceeding. Strickland v. Washington, 466 U.S. 668, 

687-88 (1984). “The assessment of prejudice should proceed on the assumption that the 

decisionmaker is reasonably, conscientiously, and impartially applying the standards that govern the 

decision.” Id. at 695. 

 Relying on our decision in United States v. Savage, 542 F.3d 959 (2d Cir. 2008), Alnutt first 

argues that his trial counsel should have objected to the calculation of the base offense level. In that 

case, which was decided several months before Alnutt was sentenced, we held that a conviction 

under Connecticut General Statute § 21a-277(b) did not categorically qualify as a controlled 
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substance offense for purposes of United States Sentencing Guidelines § 2K2.1(a)(4)(A). Id. at 965. 

We reasoned that the statute plainly criminalizes “a mere offer to sell a controlled substance,” which 

is innocent conduct under federal law. Id. Alnutt contends that his conviction under New York 

Penal Law § 220.39 similarly criminalizes a “mere offer to sell a controlled substance.” But as we 

recently observed, unlike the Connecticut statute at issue in Savage, which includes within its scope 

fraudulent offers to sell, the New York statute criminalizes only “a bona fide offer.” Pascual v. 

Holder, 723 F.3d 156, 159 (2d Cir. 2013) (citations omitted). Our ruling in Pascual was based, in part, 

on a 2002 New York Court of Appeals decision interpreting the extent of liability under the statute 

at issue, which held “that in order to support a conviction under an offering for sale theory, there 

must be a bona fide offer to sell—i.e., that defendant had both the intent and the ability to proceed 

with the sale.” People v. Samuels, 99 N.Y.2d 20, 24 (2002) (quotations and citation omitted). 

Therefore, any objection relying on Savage would have been futile because a “decisionmaker . . . 

impartially applying the standards that govern the decision” would have found that the two statutes 

are distinguishable based on the holding in Samuels. Strickland, 466 U.S. at 695. 

 With respect to the criminal history calculation, Alnutt argued below that there was 

insufficient evidence to establish his criminal conviction for the possession of narcotics. In support, 

he provided his official criminal history record maintained by the New York State Division of 

Criminal Justice Services that showed he was “not arraigned” on his drug possession offense and 

that, in April 1988, he had been sentenced only on his bail jumping conviction. The Government 

did not oppose this claim below, which was raised for the first time in the District Court in Alnutt’s 

reply to the Government’s opposition, and it now seeks to introduce evidence of his conviction on 

appeal. That evidence includes a handwritten note from the Onondaga County Clerk’s Office to the 

Probation Department attaching, inter alia, the state court minutes showing that Alnutt pleaded guilty 

to the drug possession offense and his certificate of commitment on that offense. 

 Generally, we review only material that is part of the record below, which includes the 

papers and exhibits filed in the district court, transcripts of proceedings, and a certified copy of the 

district court docket entries. Fed. R. App. P. 10(a). “Absent extraordinary circumstances, an 

appellate court will not enlarge the record to include evidentiary material not presented to the trier 

of fact.” In re MacMillan, Inc., 107 F.3d 3 (2d Cir. 1997). However, Rule 10(e)(2) provides that, “[i]f 

anything material to either party is omitted from or misstated in the record by error or accident, the 

omission or misstatement may be corrected and a supplemental record may be certified” by this 

Court. Fed. R. App. P. 10(e)(2)(C). To supplement the record pursuant to Rule 10(e)(2), a party 

must “provide evidence of an erroneous or accidental omission of material evidence.” Leibowitz v. 

Cornell Univ., 445 F.3d 586, 592 n.4 (2d Cir. 2006). Pursuant to Rule 10(e), we may also on our “own 

initiative” direct supplementation of the record if the materials “bear heavily on the merits of 

appellant’s claim” and that claim was presented for the first time on appeal. United States v. Aulet, 

618 F.2d 182, 187 (2d Cir. 1980). 
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 Here, the Government’s motion to supplement the record should be granted. Although on 

appeal the Government failed to provide any reasons or evidence as to why the record should be 

supplemented, as is required, see Leibowitz, 445 F.3d at 592 n.4, we may direct supplementation on 

our own initiative, see Aulet, 618 F.2d at 187. The new material is relevant only to Alnutt’s second 

claim, which was asserted for the first time in his reply to the Government’s opposition. Alnutt’s 

method of raising his claim was unorthodox and arguably improper.1 See United States v. Gigante, 39 

F.3d 42, 50 n.2 (2d Cir. 1994) (“Arguments may not be raised for the first time in a reply brief.”). 

Nonetheless, the Government should have objected on procedural grounds or opposed the claim on 

its merits below—especially in light of the fact that it was given approximately a year to do so. But 

equity requires both sides of a controversy to “have acted fairly and without fraud or deceit as to the 

controversy in issue.” Precision Instrument Mfg. Co. v. Auto. Maint. Mach. Co., 324 U.S. 806, 814-15 

(1945) (quotation marks and citation omitted). Inasmuch as the issue arises, in part, because Alnutt 

did not properly assert entitlement to relief in his original § 2255 motion, he should not now be able 

to prevent us from examining the evidence relevant to the correct adjudication of his claim. 

 These records demonstrate that any objection by counsel to the calculation of Alnutt’s 

criminal history would have been frivolous. The U.S. Probation Office contacted the Onondaga 

County Clerk’s Office to inquire about Alnutt’s drug possession conviction. In response, the Clerk 

provided, inter alia, the state court minutes showing that Alnutt pleaded guilty to the drug possession 

offense and his certificate of commitment on that offense. In light of this evidence, which would 

have been introduced by the Government if trial counsel had objected to the calculation of Alnutt’s 

criminal history during the original criminal proceedings, the District Court would have concluded 

that the Probation Office had sufficient facts to determine, by a preponderance of the evidence, that 

Alnutt had a prior narcotics conviction. As a result, this claim also fails. 

We have considered Alnutt’s remaining contentions in support of his two claims and his 

opposition to the Government’s motion and find them to be meritless. Accordingly, we GRANT

the Government’s motion to supplement the record and AFFIRM the district court’s order denying 

relief under 28 U.S.C. § 2255. 

 FOR THE COURT: 

 Catherine O’Hagan Wolfe, Clerk 

 1 This principle is even more salient in habeas proceedings because of AEDPA’s one year filing 

deadline, which bars claims not raised in the original petition or motion if the belatedly asserted claims 

articulate a new ground for relief. See Mayle v. Felix, 545 U.S. 644, 657 (2005).