Court Opinion

ID: 2960238
Source: CourtListenerOpinion
Date Created: 2015-09-17 17:45:33.584122+00
Date Added: 2024-06-11T12:46:21.456924
License: Public Domain

No. 06-4970-cr;
     United States v. Triumph Capital (Spadoni)

 1                                   UNITED STATES COURT OF APPEALS

 2                                          FOR THE SECOND CIRCUIT
 3                                             _________________

 4                                                 August Term 2007

 5            (Argued: March 28, 2008)                                   (Decided: September 25, 2008 )

 6                                                Docket No. 06-4970-cr
 7                                                 _______________

 8                                       UNITED STATES OF AMERICA,

 9                                                       Appellee,

10                                                       -against-

11   TRIUMPH CAPITAL GROUP, INC., FREDERICK W. MCCARTHY, LISA A. THIESFIELD,
12                              BEN F. ANDREWS,

13                                                     Defendants,

14                                             CHARLES B. SPADONI,
15                                                                                   Defendant-Appellant.
16   ______________

17   Before: POOLER, HALL, Circuit Judges, and GLEESON, District Judge.1

18           Charles B. Spadoni appeals from a judgment of the United States District Court for the
19   District of Connecticut convicting him of racketeering, racketeering conspiracy, bribery, wire
20   fraud, and obstruction of justice and sentencing him principally to a 36-month term of
21   imprisonment. Appellant claims that there is insufficient evidence to sustain his convictions, and
22   in the alternative that he is entitled to a new trial due to government suppression of exculpatory
23   evidence and improper jury instructions regarding the obstruction of justice count.

24           Reversed and remanded for a new trial on the racketeering, racketeering conspiracy,
25   bribery and wire fraud counts. The conviction on the obstruction count is affirmed, but the
26   sentence is vacated and the case is remanded for resentencing on that count.

             1
                       The Honorable John Gleeson of the United States District Court for the Eastern District of New
     York, sitting by designation.
 1                                                  JOHN H. DURHAM, Deputy United States
 2                                                  Attorney for the District of Connecticut (William J.
 3                                                  Nardini, Nora R. Dannehy, Assistant United States
 4                                                  Attorneys, Of Counsel, on the Brief), for Appellee.

 5                                                  RICHARD M. ASCHE, Litman, Asche & Gioiella,
 6                                                  LLP (Russell M. Gioiella, Litman, Asche &
 7                                                  Gioiella, LLP, on the Brief), New York, NY, for
 8                                                  Defendant-Appellant.

 9   JOHN GLEESON, United States District Judge:

10          Charles B. Spadoni appeals from a judgment of the United States District Court for the

11   District of Connecticut convicting him of racketeering, racketeering conspiracy, bribery, wire

12   fraud and obstruction of justice and sentencing him principally to a 36-month term of

13   imprisonment in connection with a political bribery scheme. Spadoni challenges the sufficiency

14   of the evidence of his intent to offer a bribe, and argues that the government unconstitutionally

15   suppressed material exculpatory and impeaching evidence. He also claims that the evidence was

16   insufficient to establish the intent element of his obstruction of justice charge, and that the jury

17   was improperly instructed on that element. While we find the evidence sufficient to sustain the

18   jury’s verdicts, we reverse and remand for a new trial on the racketeering, racketeering

19   conspiracy, bribery and wire fraud counts because we conclude that the government suppressed

20   material exculpatory and impeaching evidence. However, because we conclude that the district

21   court properly instructed the jury on the obstruction of justice charge, we affirm Spadoni’s

22   conviction on that count, but we vacate the sentence and remand for resentencing on that count.

23                                             BACKGROUND

24   A.     The Trial Evidence

                                                       2
 1          In July of 1997, Paul J. Silvester, who was at the time the Deputy Treasurer of the State

 2   of Connecticut, was appointed Treasurer to fill a midterm vacancy. The Connecticut Treasurer’s

 3   Office manages billions of dollars in state pension funds, and the Treasurer has the authority to

 4   make investment decisions for these funds. At the time Silvester joined the Treasurer’s Office, a

 5   Boston-based private equity firm, Triumph Capital Group, Inc. (“Triumph”), was managing some

 6   of the state pension fund’s investments.

 7          Silvester was friends with Spadoni, a politically active lawyer in Connecticut. In 1997,

 8   Silvester helped Spadoni get hired as Triumph’s general counsel.

 9          1.      The Campaign Contribution Bribe

10          In 1998, Silvester, who had been an interim appointment as Treasurer, decided to run for

11   a full term and needed to raise funds for his campaign. As state law prohibited investment firms

12   doing business with the Treasurer’s Office from contributing to the race for Treasurer, Silvester

13   instead attempted to raise money for the Connecticut Republican Party, which agreed to

14   contribute 70% of the amount Silvester raised to Silvester’s campaign.

15          Silvester told Spadoni that it would be “helpful” to his campaign if Triumph could raise

16   money for the Connecticut Republican Party, Trial Tr. vol. 5, 115, June 19, 2003, and Triumph

17   accordingly made a $100,000 commitment to the party. Additionally, Silvester told Spadoni that

18   he would like to have one of his employees, Lisa Thiesfield, serve as his full-time campaign

19   manager, but she was not permitted to perform campaign activities during her work hours at the

20   Treasurer’s Office. Spadoni subsequently informed Silvester that Triumph hired Thiesfield for

21   an assignment unrelated to state business, paying her a $20,000 to $25,000 fee. This allowed

22   Thiesfield to quit her Treasurer’s Office job and work as a full-time campaign manager.

                                                      3
 1            Silvester lost the election, and Spadoni promptly approached him to propose an

 2   investment deal with Triumph. Silvester decided to invest $150 million of state pension funds

 3   with Triumph before he left office, an amount comparable to the size of Triumph’s previous

 4   contracts with the state. Silvester thought the deal made good business sense, but would

 5   “probably not” have agreed to this deal if Triumph had not donated $100,000 to the Connecticut

 6   Republican Party and hired Thiesfield. Trial Tr. vol. 5, 156.

 7            2.      The Consulting Contracts Bribe

 8            Before the $150 million investment agreement was finalized, Silvester asked Spadoni to

 9   pay Thiesfield and Christopher Stack, a close associate of Silvester, a 1% finder’s fee even

10   though they had not in fact acted as finders in connection with the deal.

11            Thiesfield was unemployed due to her resignation from the Treasurer’s Office to serve as

12   Silvester’s campaign manager, and Silvester was concerned about finding employment for her

13   and for his other staffers. Stack was not an employee of the Treasurer’s Office, but he had acted

14   as a finder on previous investment opportunities with the state in the past.2 Silvester told

15   Spadoni that Stack’s company, Collegiate Capital, was in trouble, and that he wanted to help

16   Stack out of his financial difficulty.

17            Spadoni told Silvester that he would discuss the proposed finder’s fee arrangement with

18   Triumph’s owner, Frederick McCarthy. At trial, Silvester testified that Spadoni subsequently

19   informed him that McCarthy “did not want to pay the fee as a finder’s fee,” but wanted to wait

20   until Silvester was out of office and then “work it out at that point,” which Silvester understood

              2
                      Unbeknownst to Spadoni, Stack had previously given Silvester illegal kickbacks of portions of his
     finder’s fees.

                                                             4
 1   to mean that he and Triumph would later devise some arrangement that would be economically

 2   identical to the finder’s fee he had proposed. Trial Tr. vol. 5, 161-62.3 Silvester testified that this

 3   influenced him to increase the amount of funds being invested from $150 million to $200 million

 4   in order to increase the amount that Stack and Thiesfield would receive, but he did not discuss

 5   with Spadoni this decision to increase the value of the contract.

 6            On November 12, 1998, Silvester executed a $200 million investment contract with

 7   Triumph-Connecticut II, L.P., a partnership that Triumph created to invest these funds. At some

 8   point Stack and Thiesfield, each using a wholly-owned LLC, executed a consulting contract with

 9   Triumph which would pay each $1,000,000 over three years. The government claimed at trial

10   that these were sham contracts under which Stack and Thiesfield assumed virtually no duties and

11   were paid regardless of any results, contrary to industry practice.

12            At trial, the date on which Stack’s contract was signed was the subject of dispute. Stack

13   testified that his contract was signed on November 11, 1998, a day before the investment contract

14   was executed, and that his contract was postdated to appear that it was executed after Silvester

15   left office in January of 1999. Stack testified that he remembered that this was the date his

16   contract was signed because he found tickets to a matinee he had attended on that date, and he

17   remembered that he signed the contract on the same day that he attended the matinee. Visitor

18   logs from the law firm offices where Stack testified that he signed the contract confirmed that a

19   meeting involving Stack, Spadoni and McCarthy took place on that date. Stack also testified that

              3
                        As discussed below, Silvester initially provided a different account of this interaction to
     investigators through his attorney, and the failure to disclose that initial version underlies Spadoni’s Brady claim on
     this appeal.

                                                                5
 1   he received a draft contract by fax shortly before the signing, and Triumph’s records reflect that

 2   Triumph sent a fax to Stack on November 9, 1998.

 3            However, on several occasions during the course of his cooperation with the government,

 4   Stack told prosecutors that his consulting contract was signed at the end of December in 1998,

 5   between Christmas and New Year’s Day. When he was first interviewed by the government,

 6   Stack made no mention of the November 11, 1998 meeting at the law firm and instead stated that

 7   he first learned of a possible consulting contract while vacationing in Tortola after Triumph’s

 8   investment contract with Connecticut was signed. According to Stack, Silvester and Thiesfield

 9   were also vacationing with him in Tortola, and Silvester told him that he would later get a

10   consulting contract.4 Stack also told the government that by the time the consulting contract was

11   eventually signed, the Triumph-Connecticut investment contract had already been fully funded,

12   which did not happen until December 4, 1998.

13            Although Silvester was not present for the signing of Stack’s consulting contract, his trial

14   testimony indicated that the consulting contract was signed after the investment contract between

15   Triumph and Connecticut. Specifically, Silvester testified that after he and Stack returned from

16   Tortola, which was after the investment contract was signed, Spadoni told him that McCarthy

17   was “favorably inclined” to enter into a contract with Stack. Trial Tr. vol. 6, 59, June 20, 2003.

18   He also testified that he and Stack discussed Stack’s arrangements to sign the contract in mid-

              4
                        At trial, Stack also testified that while he was in Tortola, the day after he allegedly signed the $1
     million contract, he was in a bad mood because of his company’s financial difficulties.

                                                                 6
 1   December 1998 or later, and that it was his understanding that Stack’s consulting contract was

 2   signed in December 1998 or in January 1999.5

 3            3.       Obstruction of Justice

 4            Shortly after Silvester left office, the investments he made late in his term came under

 5   scrutiny. On May 25, 1999, a grand jury subpoena was served on Triumph-Connecticut II, L.P.

 6   calling for the production of records related to the investment contract. Triumph-Connecticut II,

 7   L.P. complied with this subpoena.

 8            Shortly after the subpoena was served, Spadoni told Silvester about it. He said that

 9   Triumph did not believe its consulting contracts with Stack and Thiesfield were covered by the

10   subpoena, but that Triumph’s lawyers anticipated more subpoenas in the future. Spadoni spoke

11   to Silvester again and told him that an attorney had advised him to destroy documents not called

12   for by subpoena in anticipation of further subpoenas, and had recommended specialized deletion

13   software to remove them from his computer. He also asked Silvester to destroy any copies he

14   might have of a contract between Silvester’s new employer, Park Strategies, and a company

15   owned by Ben Andrews, an eventual co-defendant of Spadoni on unrelated charges.

16            On July 13, 1999, the grand jury issued another subpoena, which led Triumph to produce

17   the Stack and Thiesfield consulting contracts. On December 29, 1999, the grand jury issued an

18   additional subpoena, which led to the production of backup tapes from Triumph’s computer

19   networks.

              5
                      In addition, Silvester testified that Thiesfield’s contract was signed in January 1999, after she
     returned from a December 1998 trip to California.

                                                                7
 1          On April 11, 2000, the grand jury subpoenaed a Triumph laptop computer assigned to

 2   Spadoni. An FBI forensic computer examiner testified at trial that his inspection of the laptop

 3   revealed that a copy of the commercial document deletion software “Destroy-It!” was installed

 4   on the computer on June 21, 1999, and used to delete files in a directory named “Triumph” on

 5   June 23, 1999. On December 28, 1999, the software was used to delete two files in a directory

 6   named “LAT, LLC,” which was the name of Thiesfield’s wholly-owned company.

 7          Among the documents deleted from the laptop were files named “Stack Contract” and

 8   “LAT Contract.” These files were accessed on November 16, 1998, and at the time they had last

 9   been modified on November 10, 1998. The forensic examiner testified that “Stack Contract” was

10   also accessed on November 23, 1998 and May 31, 1999, but he could not determine whether this

11   file was accessed or modified between November 23, 1998 and December 31, 1998. “LAT

12   Contract” was accessed on June 3, 1999 and December 31, 1999. The document deletion

13   software was also used to remove files called “Park Strategies Agreement,” “Engagement

14   Letter,” and others apparently unrelated to this case.

15          At one point after the investigation began, Triumph’s comptroller, Robert Trevisani,

16   discussed with Spadoni how to destroy computer files securely, and remarked, “if we were trying

17   to hide something, we could use a program like CleanSweep.” Trial Tr. vol. 7, 217, June 24,

18   2003. Spadoni informed Trevisani that the program he needed “would be Destroy-It!.” Id.

19          Stack approached the government early in its investigation and offered to reveal

20   Silvester’s dealings in exchange for immunity. Silvester subsequently pled guilty to criminal

21   conduct involving five funds doing business with the State of Connecticut. He pled guilty to

                                                       8
 1   bribery with respect to three of those funds, and to mail fraud with respect to Triumph and

 2   another fund.

 3   B.       The Procedural History

 4            Triumph, Spadoni, Thiesfield, McCarthy, and Andrews were charged in a superseding

 5   indictment on January 9, 2001, and Spadoni was tried along with Triumph in June and July of

 6   2003.6 At trial, the district court instructed the jury that it could return a conviction on the

 7   obstruction of justice charge if it found that “in the defendant’s mind, his or its conduct had the

 8   natural and probable effect of obstructing or interfering with the grand jury proceeding.” Trial

 9   Tr. vol. 16, 123, July 10, 2003. In giving this charge, the district court denied Spadoni’s request

10   to insert the words “he knew that” after “the defendant’s mind.”7

11            On July 16, 2003, the jury acquitted Spadoni of the charges related to the campaign

12   contributions bribe, but convicted him of bribery and mail fraud in connection with the

13   consulting contracts bribe and of obstruction of justice. It found the racketeering act based on the

14   campaign contributions bribe not proven, but found the racketeering acts based on the consulting

15   contracts bribe and the obstruction of justice counts proven, and convicted Spadoni of

16   racketeering and racketeering conspiracy.

17            Spadoni moved for a judgment of acquittal or a new trial, challenging the sufficiency of

18   the evidence supporting his convictions on all counts. On September 16, 2005, the district court

              6
                       Thiesfield and McCarthy pled guilty to bribery charges. Andrews was tried and convicted
     separately.

              7
                       This objection is recorded in Spadoni’s undated written statement of his exceptions to the jury
     instructions. This statement indicates that the objections were made during the preliminary and final charge
     conferences, which were both held off the record in chambers. Def.’s Exceptions to Jury Instructions 1. The
     government does not object to the accuracy of this document.

                                                               9
 1   denied this motion with respect to the bribery, wire fraud, and obstruction of justice counts but

 2   found Spadoni entitled to a judgment of acquittal on the racketeering and racketeering conspiracy

 3   charges. United States v. Spadoni (Spadoni I), No. 00-CR-217 (EBB), 2005 WL 2275938, at *11

 4   (D. Conn. Sept. 16, 2005). The district court later reinstated the conviction on the racketeering

 5   and racketeering conspiracy charges. United States v. Spadoni (Spadoni III), No. 00-CR-217

 6   (EBB), 2006 WL 2771642, at *2 (D. Conn. Sept. 11, 2006).8

 7           Spadoni also moved for a new trial based on claims that the prosecution suppressed

 8   material exculpatory and impeaching evidence in violation of Brady v. Maryland, 373 U.S. 83

 9   (1963), and Giglio v. United States, 405 U.S. 150 (1972). After the trial, Spadoni’s counsel

10   acquired from Silvester a set of notes Silvester had handwritten for his attorneys, Hubert Santos

11   and Hope Seely. These notes, which had been created to assist Santos in conducting plea

12   negotiations on Silvester’s behalf, had also been typewritten verbatim by Santos’s office.

13   Spadoni’s counsel drafted an affidavit for Silvester to sign, and represented to the district court

14   that Silvester edited the affidavit and offered to testify to its truth if subpoenaed but refused to

15   sign it due to a fear that it could adversely affect his community confinement status. The

16   unexecuted affidavit indicates that Silvester’s attorney met with the government in an attorney

17   proffer and that he conveyed to the government the substance of Silvester’s notes. An attorney

18   proffer apprises the government of what the client would be able to provide by way of testimony,

19   and is often the first step in a defendant’s effort to obtain a cooperation agreement with the

             8
                        This was the third written memorandum opinion in Spadoni’s case because it followed the district
     court’s denial of Spadoni’s motion for a new trial pursuant to Brady v. Maryland, 373 U.S. 83 (1963), and Giglio v.
     United States, 405 U.S. 150 (1972), discussed in more detail infra. See United States v. Spadoni (Spadoni II), No.
     00-CR-217 (EBB), 2006 W L 2595574, at *7 (D. Conn. Sept. 7, 2006) (denying Brady/Giglio motion).

                                                             10
 1   government. The unexecuted Silvester affidavit also states that he personally conveyed the same

 2   information to the government when he began cooperating.

 3           Silvester’s notes detail corrupt activity by Silvester in connection with several entities.

 4   They also include a version of Silvester’s interaction with Spadoni that is somewhat different

 5   from Silvester’s trial testimony. The notes, written in Silvester’s voice, state:

 6                    I told Charlie [Spadoni] to pay a finder to Stack and Theisfield
 7                    [sic] and then I wanted Triumph to hire Elizabeth and Mike
 8                    MacDonald also. He said he would take it up with Fred
 9                    [McCarthy]. He came back and said they would not pay any finder
10                    or offer employment to anyone connected to me in exchange for
11                    the deal. Charlie said it would be quid pro quo and he could not
12                    advise his boss to agree to it. Charlie said that Fred was
13                    sympathetic to the situation of certain staffers and they would be as
14                    helpful as possible after I left office but that it would have to be
15                    arms length and make sense for Triumph. I said fine.

16   Gioiella Decl. Ex. A, June 13, 2005.

17           In response to Spadoni’s Brady motion, the government produced, for the first time, notes

18   taken by FBI Special Agent Charles E. Urso during the attorney proffer. These notes state, in

19   part:

20                    PS told CS -told
21                    pay Stack + Lisa T. -fees-
22                    CS would not pay finder-
23                    Employee- MM-EW-
24                    CS told could [not] pay related to a deal.
25                    McCarthy sympathetick [sic] to staff-
26                    arms length needed to make sense-

27   Gov.’s Resp. to Gioiella Decl. Attach. A.9

             9
                       Although the note omits the word “not,” the government agrees that Agent Urso intended to write
     “could not pay related to a deal” and left out the word “not” merely as an oversight.

                                                             11
 1          The government argued that it never possessed Silvester’s handwritten or typewritten

 2   notes. It further argued that the information in those notes and in Urso’s notes was not material

 3   exculpatory or impeaching information because it was consistent with Silvester’s pretrial

 4   interviews with the government, his grand jury testimony, and his trial testimony. The relevant

 5   FBI report summarizing Silvester’s pretrial interview with the government reads, in part:

 6                          Silvester proposed to Spadoni that he would like Stack and
 7                  Thiesfield to be paid as finders . . . . Silvester told Spadoni he
 8                  wanted them to be paid a point, split between the two. Spadoni
 9                  said he would take it up with McCarthy.
10                          Spadoni related that it was a problem (legal reasons) when
11                  Silvester was in office but he would be glad to sit with them after
12                  he was out of office. Silvester understood that Spadoni would start
13                  the process of hiring Thiesfield and Stack during negotiations.

14   Id. Attach. B. Before the grand jury, Silvester described the situation similarly, saying that after

15   he proposed the finder’s fee to Spadoni, Spadoni checked with McCarthy, “came back, said that

16   they would rather sit with them separately after I was out of office and work it with them at that

17   time.” Grand Jury Tr. 58-59, June 13, 2000.

18          Silvester’s statements in pretrial interviews and before the grand jury were consistent

19   with his trial testimony. At trial, Silvester said that Spadoni indicated that Triumph “did not

20   want to pay the fee as a finder’s fee” but instead “wanted to wait until [Silvester] was out of

21   office and then sit with those folks and work it out at that point.” Trial Tr. vol. 5, 161. Silvester

22   testified that he took this to mean “that they would sit and work it out on terms similar to the

23   economics that [he and Spadoni] had discussed.” Id. at 162.

24          On September 7, 2006, the district court denied Spadoni’s Brady motion, finding that the

25   government did not possess Silvester’s notes and that the information contained in both Urso’s

                                                      12
 1   and Silvester’s notes was not materially different from the content of Silvester’s pretrial

 2   interviews, grand jury testimony and trial testimony. United States v. Spadoni (Spadoni II), No.

 3   00-CR-217 (EBB), 2006 WL 2595574, at *5-*6 (D. Conn. Sept. 7, 2006).

 4          On October 25, 2006, the district court sentenced Spadoni principally to concurrent 36-

 5   month terms of imprisonment on all counts and a $50,000 fine. This appeal followed.10

 6                                                DISCUSSION

 7   A.     The Legal Standards

 8          1.      Motion for a Judgment of Acquittal

 9          Federal Rule of Criminal Procedure 29 provides that after a jury verdict, “the court on the

10   defendant’s motion must enter a judgment of acquittal of any offense for which the evidence is

11   insufficient to sustain a conviction.” Fed. R. Crim. P. 29(a); see also Fed. R. Crim. P. 29(c)(1)

12   (allowing for such motions after jury verdicts). “A defendant challenging the sufficiency of the

13   evidence supporting a conviction faces a ‘heavy burden.’” United States v. Glenn, 312 F.3d 58,

14   63 (2d Cir. 2002) (quoting United States v. Matthews, 20 F.3d 538, 548 (2d Cir. 1994)). A court

15   may overturn a conviction on this basis “only if, after viewing the evidence in the light most

16   favorable to the Government and drawing all reasonable inferences in its favor,” it finds that “‘no

17   rational trier of fact’ could have concluded that the Government met its burden of proof.” Glenn,

18   312 F.3d at 63 (quoting United States v. Morrison, 153 F.3d 34, 49 (2d Cir. 1998)). “‘[T]he

19   relevant question is whether . . . any rational trier of fact could have found the essential elements

20   of the crime beyond a reasonable doubt.’” Glenn, 312 F.3d at 63 (quoting Jackson v. Virginia,

            10
                    Spadoni remains on bond pending the outcome of this appeal.

                                                         13
 1   443 U.S. 307, 319 (1979)). A court’s analysis considers “‘the evidence in its totality,’ and the

 2   Government ‘need not negate every theory of innocence.’” Glenn, 312 F.3d at 63 (quoting

 3   United States v. Autuori, 212 F.3d 105, 114 (2d Cir. 2000)).

 4             In order to “‘avoid usurping the role of the jury,’” Autuori, 212 F.3d at 114 (quoting

 5   United States v. Guadagna, 183 F.3d 122, 129 (2d Cir. 1999)), courts must “‘defer to the jury’s

 6   assessment of witness credibility and the jury’s resolution of conflicting testimony’” when

 7   reviewing the sufficiency of the evidence. Glenn, 312 F.3d at 64 (quoting United States v. Bala,

 8   236 F.3d 87, 93-94 (2d Cir. 2000)); see also, e.g., Autuori, 212 F.3d at 114 (“We may not

 9   substitute our own determinations of credibility or relative weight of the evidence for [those] of

10   the jury.”). The relevant inquiry is “‘whether upon the evidence, giving full play to the right of

11   the jury to determine credibility, weigh the evidence, and draw justifiable inferences of fact, a

12   reasonable mind might fairly conclude guilt beyond a reasonable doubt.’” Autuori, 212 F.3d at

13   114 (quoting United States v. Mariani, 725 F.2d 862, 865 (2d Cir. 1984)).

14             Where a fact to be proved is also an element of the offense, however, “it is not enough

15   that the inferences in the government’s favor are permissible.” United States v. Martinez, 54

16   F.3d 1040, 1043 (2d Cir. 1995). A court “must also be satisfied that the inferences are

17   sufficiently supported to permit a rational juror to find that the element, like all elements, is

18   established beyond a reasonable doubt.” Id. “[I]f the evidence viewed in the light most

19   favorable to the prosecution gives ‘equal or nearly equal circumstantial support to a theory of

20   guilt and a theory of innocence,’ then ‘a reasonable jury must necessarily entertain a reasonable

21   doubt.’” Glenn, 312 F.3d at 70 (quoting United States v. Lopez, 74 F.3d 575, 577 (5th Cir.

22   1996)).

                                                       14
 1          We review a district court’s denial of a motion for a judgment of acquittal de novo,

 2   “applying the same standard of sufficiency as the district court.” United States v. Florez, 447

 3   F.3d 145, 154 (2d Cir. 2006).

 4          2.      Motion for A New Trial

 5          Federal Rule of Criminal Procedure 33(a) provides that “[u]pon the defendant’s motion,

 6   the court may vacate any judgment and grant a new trial if the interest of justice so requires.”

 7   Fed. R. Crim. P. 33(a). “Generally, a motion for a new trial ‘should not be granted unless the

 8   trial court is convinced that the jury has reached a seriously erroneous result or that the verdict is

 9   a miscarriage of justice.’” Smith v. Carpenter, 316 F.3d 178, 183 (2d Cir. 2003) (quoting Atkins

10   v. N.Y. City, 143 F.3d 100, 102 (2d Cir. 1998)). A district court has “broad discretion . . . to set

11   aside a jury verdict and order a new trial to avert a perceived miscarriage of justice.” United

12   States v. Ferguson, 246 F.3d 129, 133 (2d Cir. 2001) (quoting United States v. Sanchez, 969 F.2d

13   1409, 1413 (2d Cir. 1992)). Though a district court is entitled to “weigh the evidence and in so

14   doing evaluate for itself the credibility of the witnesses,” Sanchez, 969 F.2d at 1413 (internal

15   quotation marks omitted), it “must strike a balance between weighing the evidence and

16   credibility of witnesses and not ‘wholly usurp[ing]’ the role of the jury,” Ferguson, 246 F.3d at

17   133 (quoting Autuori, 212 F.3d at 120). While courts have “broader discretion to grant a new

18   trial under Rule 33 than to grant a motion for acquittal under Rule 29,” they “nonetheless must

19   exercise the Rule 33 authority ‘sparingly’ and in ‘the most extraordinary circumstances.’”

20   Ferguson, 246 F.3d at 134 (quoting Sanchez, 969 F.2d at 1414).

                                                       15
 1          We review the district court’s denial of a new trial motion for abuse of discretion, e.g.,

 2   United States v. Rivas, 377 F.3d 195, 199 (2d Cir. 2004), but we review the district court’s

 3   factual findings only for clear error, United States v. Imran, 964 F.2d 1313, 1318 (2d Cir. 1992).

 4   B.     The Sufficiency of the Evidence of the Consulting Contracts Bribe

 5          Spadoni argues that there is insufficient evidence to support the jury’s verdict finding him

 6   guilty of bribery and wire fraud with respect to the consulting contracts bribe or the jury’s finding

 7   that the corresponding racketeering act was proved. Specifically, he claims that the government

 8   failed to produce sufficient evidence to enable a reasonable jury to conclude, beyond a reasonable

 9   doubt, that Spadoni intended to influence Silvester to increase the size of the Triumph-

10   Connecticut contract. We disagree.

11          Spadoni argues that the government never produced any evidence that he and Silvester

12   ever discussed increasing the size of the investment contract or that Spadoni had any indication

13   that Silvester was considering such an increase. It is true that Silvester did not testify that he

14   explicitly indicated that he would increase the size of the investment contract. However, he did

15   testify that he asked Spadoni for contracts by which Triumph would pay Silvester’s associates

16   “finder’s fees,” which would be a percentage of the total investment contract amount. According

17   to Silvester, Spadoni told him that while Triumph could not pay finder’s fees to Silvester’s

18   associates at that time, Triumph would be happy to “work it out” when Silvester left office. Trial

19   Tr. vol. 5, 161. Silvester testified that he interpreted this response as an agreement to work out

20   the details of an arrangement economically identical to a finder’s fee.

21          The jury could have credited this testimony and inferred that Spadoni agreed to

22   percentage-based contracts in order to induce Silvester to maximize the return to his associates

                                                       16
 1   by increasing the size of the investment contract. Additionally, the jury heard evidence

 2   indicating that Stack’s contract was signed a day before the investment contract was executed;

 3   that the Stack and Thiesfield consulting contracts were fraudulently postdated until after Silvester

 4   left office; and that -- just like Silvester’s proposed finder’s fee arrangement -- the Stack and

 5   Thiesfield contracts assigned them no real duties but paid the two of them 1% of the amount of

 6   the investment contract. The jury could reasonably have credited this evidence and found it to

 7   support the inference not only that Spadoni was aware that the consulting contracts were corrupt,

 8   but also that he intentionally structured them so as to conform to Silvester’s proposal and to give

 9   Silvester an incentive to increase the size of the investment contract.

10            Spadoni argues that even if the evidence was sufficient to warrant a reasonable jury’s

11   finding that he likely possessed the requisite intent, it was not sufficient to support this

12   conclusion beyond a reasonable doubt. However, viewed in the light most favorable to the

13   government, the foregoing evidence strongly indicates Spadoni’s guilt. Spadoni’s efforts to

14   obstruct the investigation evidence a consciousness of guilt that further supports the jury’s

15   verdicts. See United States v. Robinson, 635 F.2d 981, 986 (2d Cir. 1980) (finding evidence of

16   obstruction of the government’s investigation admissible to show consciousness of guilt); see

17   also United States v. Malpiedi, 62 F.3d 465, 467 (2d Cir. 1995) (similar). Accordingly, the jury’s

18   verdicts were supported by sufficient evidence.11

              11
                         Spadoni takes issue with the district court’s statement, in its decision denying his insufficiency
     challenge, that the jury could reasonably have inferred that the consulting contracts were intended to induce Silvester
     to enter into the investment contract in the first place. See Spadoni I, 2005 W L 2275938, at *6 (“Regardless of
     whether Spadoni and McCarthy knew of Silvester’s intent to increase the investment, they agreed to pay Stack and
     Thiesfield the equivalent of finder’s fees in an attempt to influence Silvester’s decision to invest in Triumph
     Capital.”). The government’s theory in the indictment and bill of particulars, and at trial, was that the campaign
     contribution bribes -- of which Spadoni was acquitted -- were the sole incentive for Silvester to enter into the

                                                               17
 1   C.       The Brady/Giglio Motion

 2            Spadoni argues that the district court abused its discretion in denying his motion for a

 3   new trial on the ground that the government unconstitutionally suppressed material exculpatory

 4   and impeaching evidence. We agree.

 5            The government has a duty to disclose all material evidence favorable to a criminal

 6   defendant. E.g., United States v. Madori, 419 F.3d 159, 169 (2d Cir. 2005) (citing Brady v.

 7   Maryland, 373 U.S. 83, 87 (1963); see also Giglio v. United States, 405 U.S. 150, 154-55 (1972)

 8   (applying Brady to material that can be used to impeach prosecution witnesses). When the

 9   government violates this duty and obtains a conviction, it deprives the defendant of his or her

10   liberty without due process of law. E.g., Rivas, 377 F.3d at 199.

11            “A Brady violation occurs when the government fails to disclose evidence materially

12   favorable to the accused.” Youngblood v. West Virginia, 547 U.S. 867, 869 (2006). Evidence

13   that is not disclosed is suppressed for Brady purposes even when it is “known only to police

14   investigators and not to the prosecutor.” Kyles v. Whitely, 514 U.S. 419, 438 (1995). Evidence is

15   favorable if it is either exculpatory or impeaching. See, e.g., Strickler v. Greene, 527 U.S. 263,

16   281-82 (1999). Evidence is material if “there is a reasonable probability that, had the evidence

17   been disclosed to the defense, the result of the proceeding would have been different.”

18   Youngblood, 547 U.S. at 870 (internal quotation marks omitted). However, a “‘showing of

19   materiality does not require demonstration by a preponderance of the evidence that disclosure of

     investment contract. Thus, Spadoni argues that his conviction on the consulting contracts bribe cannot be upheld by
     evidence suggesting that it was intended to induce the creation of the contract. Given that the evidence is sufficient
     for a reasonable jury to find that Spadoni intended the consulting contracts to induce Silvester to increase the size of
     the investment, we have no occasion to address this contention.

                                                               18
 1   the suppressed evidence would have resulted ultimately in the defendant’s acquittal,’” id.

 2   (quoting Kyles, 514 U.S. at 434), but only a “‘showing that the favorable evidence could

 3   reasonably be taken to put the whole case in such a different light as to undermine confidence in

 4   the verdict,’” Youngblood, 547 U.S. at 870 (quoting Kyles, 514 U.S. at 435). The assessment of

 5   materiality is made in light of the entire record. United States v. Agurs, 427 U.S. 97, 112 (1976).

 6          In denying Spadoni’s Brady motion, the district court concluded that the government did

 7   not possess Silvester’s unsigned affidavit and therefore did not suppress its contents. Spadoni II,

 8   2006 WL 2595574, at *5. This factual finding was not clearly erroneous. See Imran, 964 F.2d at

 9   1318 (“We will not disturb the district court’s findings of fact in conjunction with a Rule 33

10   motion unless the findings are clearly erroneous.”).

11          However, it is undisputed that the government possessed Agent Urso’s proffer notes, and

12   that it did not disclose them until it responded to Spadoni’s post-trial motion. The district court

13   found the contents of the notes, as well as of the unsigned affidavit, not to be materially different

14   from the contents of Silvester’s statements in the disclosed FBI interview report, in his grand jury

15   testimony, and at trial. With due respect for the district court, we cannot agree with this

16   determination.

17          The district court found that Agent Urso’s proffer notes were not materially inconsistent

18   with Silvester’s other testimony based on its opinion that “[i]n every iteration of the events . . . ,

19   Spadoni’s initial response was to decline Silvester’s request to pay finder’s fees to Stack and

20   Thiesfield.” Spadoni II, 2006 WL 2595574, at *6. This characterization ignores a critical

21   difference between Agent Urso’s notes and Silvester’s later statements. The proffer notes

22   support an alternative version of the Silvester-Spadoni conversation about finder’s fees, one

                                                       19
 1   entirely at odds with the government’s theory of the case at trial. In Silvester’s later statements,

 2   including his testimony at trial, the only requests Spadoni “decline[d],” id., were the requests to

 3   characterize the payments as finders’ fees and to make the payments before Silvester left office.

 4   These later statements do not include an indication that Spadoni declined to agree to the

 5   substance of Silvester’s request. Indeed, Silvester claimed that Spadoni agreed to pursue an

 6   arrangement economically identical to Silvester’s finder’s fee proposal, but he would

 7   characterize it differently and perform it when Silvester left office. By contrast, when Silvester

 8   first proffered (through his attorney) to the government, his statements strongly suggested that

 9   Spadoni had declined to make payments that would amount to a bribe. Agent Urso’s notes, and

10   particularly the notation that Spadoni responded that the arrangement with Triumph had to be at

11   “arms length” and “needed to make sense,” suggest that Spadoni refused to enter into an

12   arrangement economically identical to Silvester’s proposal. By far the most natural interpretation

13   of these phrases in Agent Urso’s notes is that Spadoni indicated that a deal would have to make

14   economic sense and be at arm’s length; that is, that it would be anything but economically

15   identical to Silvester’s proposal.

16          The difference between the government’s final version of events and the version

17   supported by Silvester’s initial proffer, which was suppressed, is directly relevant to the intent

18   element of the consulting contract bribe charges. In the final version, Spadoni agreed in

19   substance to pay Silvester’s associates for work they did not perform, which provided strong

20   support for the jury’s finding that Spadoni intended to influence an official act and to defraud the

21   people of the State of Connecticut of their right to Silvester’s honest services. Silvester’s initial

22   version of that conversation, however, provided scant if any support for the inference that

                                                       20
 1   Spadoni possessed the requisite intent to bribe or defraud. By suppressing Urso’s notes of that

 2   proffer, the government deprived Spadoni of exculpatory evidence going to the core of its bribery

 3   case against him.

 4          Spadoni could have used the proffer notes not merely to support his version of his

 5   conversation with Silvester, but also to impeach Silvester’s credibility. While the notes did not

 6   record Silvester’s words, Spadoni could have attributed them to him through cross-examining

 7   Silvester, questioning Agent Urso, and if necessary calling Silvester’s attorney. See, e.g., United

 8   States v. Gil, 297 F.3d 93, 104 (2d Cir. 2002) (noting that Brady material need not be admissible

 9   if it “could lead to admissible evidence” or “would be an effective tool in disciplining witnesses

10   during cross-examination by refreshment of recollection or otherwise,” and citing cases).

11          The notes were taken at a meeting where Silvester’s attorney approached the government

12   on Silvester’s behalf to relate Silvester’s account of his criminal activity in an attempt to

13   convince the government to offer him a cooperation agreement. Spadoni could have argued that

14   Silvester initially authorized his attorney to tell the truth, which inculpated others and exculpated

15   Spadoni, but that once he began to cooperate with the government he fabricated a new,

16   inculpatory version of his dealings with Spadoni to enhance the value of his cooperation and his

17   expected reward. It is by no means certain that this argument would have swayed the jury, but it

18   is a real enough possibility to undermine confidence in the verdict.

19          In contending otherwise, and in maintaining that the phrases “arms length” and “needed

20   to make sense” in Agent Urso’s proffer notes do not cast the case in such a different light, the

21   government overestimates the strength of its case. Other than Silvester’s testimony, the evidence

22   regarding Spadoni’s intent was far from overwhelming. See Gil, 297 F.3d at 103 (“Where the

                                                       21
 1   evidence against the defendant is ample or overwhelming, the withheld Brady material is less

 2   likely to be material than if the evidence of guilt is thin.”). It is true that suspiciously one-sided

 3   consulting contracts with Stack and Thiesfield were eventually signed, but the timing of these

 4   contracts was hotly disputed. If the consulting contracts were signed after the investment

 5   contract was finalized, as Spadoni contends, the inference that they were intended to influence

 6   Silvester’s decision to set the final amount of the investment contract is weak absent evidence of

 7   some prior agreement or understanding. Silvester’s testimony provided evidence of such an

 8   agreement. Indeed, based on the strength of Silvester’s testimony, the government told the jury

 9   in summation that it could convict even if it found that the consulting contracts were signed after

10   the investment contract. However, in the absence of Silvester’s testimony, it would be more

11   difficult for the jury to have found that Spadoni possessed the requisite intent to influence

12   Silvester’s actions regarding the investment contract unless it found that the consulting contracts

13   themselves were signed before the investment contract was finalized.12

14            If the jury credited the government’s evidence that Stack’s consulting contract was

15   executed on November 11, 1998, the day before the investment contract, it could certainly have

16   found that Spadoni possessed the requisite intent. However, the evidence that Stack’s contract

17   was signed on that date is thin. While Triumph’s records reflect that Triumph sent him a fax on

              12
                         The district court’s instructions on the bribery and wire fraud counts charged the jury solely on a
     theory of bribery, not on an illegal gratuity theory. In instructing the jury on the bribery count, the district court
     stated that the offer of a bribe had to precede the official act being influenced. Trial Tr. vol. 16, 181. The district
     court’s instructions on the wire fraud count defined the charged scheme or artifice to defraud as simply the same
     charged bribe, referred to her previous instructions on the bribery, and noted that the bribe had to be understood to
     be offered “in exchange for an official act to be performed.” Id. at 190-91 (emphasis added). Even had the district
     court not instructed the jury that the offer of a bribe had to precede the official act, the inference of corrupt intent
     would still have been weaker had the jury found that Spadoni agreed to the consulting contracts only after the
     investment contract was finalized.

                                                                22
 1   November 9, 1998 and visitor logs confirm that Stack met with Spadoni and McCarthy on

 2   November 11, 1998, Stack’s testimony was the only evidence that the fax was a draft contract or

 3   that a contract was signed at the November 11, 1998 meeting. Moreover, Silvester corroborated

 4   Stack’s earlier statements indicating that when the two of them were in Tortola, after the signing

 5   of the investment contract, they were still discussing the future prospect of a consulting contract

 6   for Stack.

 7           In light of this factual dispute, the jury could easily have found that the consulting

 8   contract was signed after the investment contract but still convicted Spadoni based on Silvester’s

 9   account of their conversation. There is thus no reason to believe that the jury would still have

10   concluded that Spadoni possessed the requisite intent if its confidence in Silvester’s testimony

11   had been undermined. In short, the government suppressed evidence in its possession which was

12   both exculpatory and impeaching, and there is a reasonable probability that if the evidence had

13   been disclosed, the outcome of the proceeding would have been different.

14           The government argues that we must defer to the district court’s determination that the

15   remarks recorded in Agent Urso’s notes did not materially differ from Silvester’s other

16   statements, noting that the district court is in the best position to assess the impact of an omitted

17   piece of evidence on the proceedings. It is true that we review the denial of a motion for a new

18   trial for abuse of discretion in recognition of the district court’s greater familiarity with the

19   proceedings. E.g., Rivas, 377 F.3d at 199. However, we have reversed convictions based on

20   Brady violations where the district court concluded that the omitted evidence was not material in

21   circumstances at least as favorable to the government as these.

22           In United States v. Gil, we reversed a district court’s finding that a document was not

                                                       23
 1   material even though, if credited, the document would not directly establish a defense. 297 F.3d

 2   at 104-05. In that case, a general contractor accused of fraudulently inflating invoices from his

 3   subcontractors argued that he had been authorized by his clients to do so in a side deal in

 4   consideration for his performance of some additional duties. Id. at 97-98. The government

 5   suppressed a memorandum describing a meeting where the defendant agreed to perform extra-

 6   contractual work for the client and the client authorized the defendant to charge a premium on

 7   subcontractor bills. Id. at 97. The district court found that this memorandum was not material

 8   because it did not state that the defendant was authorized to collect this premium by falsifying the

 9   amounts recorded on his subcontractor invoices. Id. at 101. However, we found that in

10   providing evidence for a side deal similar to that described by the defendant, the memorandum

11   provided enough circumstantial support for the defense case that it was material. Id. at 104-05.

12   The proffer notes here, which directly tend to negate the intent element in Spadoni’s bribe

13   charges, are at least as central to the defense case as the memorandum in Gil, which did not

14   record any indication that the defendant was authorized to falsify the amounts of his

15   subcontractors’ invoices.

16          In United States v. Rivas, we reversed the district court and granted a new trial where the

17   suppressed evidence was inculpatory as well as exculpatory, because its exculpatory character

18   harmonized with the theory of the defense case. 377 F.3d at 199-00. That case concerned the

19   appeal of Edgar Rivas, a seaman convicted of smuggling cocaine in his ship cabin. Id. at 196.

20   Rivas’s cabinmate Pulgar, the key prosecution witness, testified at trial that he saw Rivas store

21   cocaine in their cabin and that Rivas had told him of Rivas’s drug trafficking activity, but no

22   evidence was produced regarding how the drugs were brought aboard the ship. Id. at 197-98.

                                                     24
 1   The government suppressed a statement in which Pulgar claimed that he had brought the cocaine

 2   onto the ship for Rivas and delivered it to him, believing it to be alcohol until Rivas admitted its

 3   true nature. Id. at 198. The district judge denied Rivas’s Brady motion, finding the suppressed

 4   testimony was not material because it was consistent with Pulgar’s trial testimony indicating that

 5   Rivas owned the drugs. Id. at 198-99. Although we acknowledged that the suppressed statement

 6   was inculpatory as well as exculpatory, we nonetheless vacated the district court’s denial of

 7   Rivas’s Brady motion and remanded for a new trial, as the statements supported the defense’s

 8   theory that Pulgar had possessed the drugs all along and blamed Rivas for them. Id. at 199-200.

 9          The proffer notes here were at least as crucial to Spadoni’s defense as Pulgar’s statement

10   was to the defense in Rivas. The government contended at oral argument that Agent Urso’s

11   proffer notes were inculpatory, arguing that Spadoni’s refusal indicated his consciousness of

12   wrongdoing. We find this argument to be strained. In any event, any inculpatory effect of

13   Spadoni’s refusal to accept Silvester’s proposal is dwarfed by its tendency to exculpate Spadoni.

14   Based on Agent Urso’s notes, Spadoni could have contended at trial that the first time Silvester

15   recounted the critical conversation with Spadoni, he told the government that Spadoni would

16   engage only in an “arm’s length” deal that would “make sense” for Triumph. The fact that Agent

17   Urso was the case agent during the investigation and at trial renders the nondisclosure of his

18   notes of the attorney proffer especially difficult to comprehend. The government could not

19   explain at oral argument why the notes were withheld. We must conclude that there is a

20   reasonable probability that if the government had not inexplicably withheld Agent Urso’s proffer

21   notes, the jury would have harbored a reasonable doubt about Spadoni’s guilt. Accordingly,

22   Spadoni is entitled to a new trial on the racketeering, racketeering conspiracy, bribery, and wire

                                                      25
 1   fraud charges.13

 2   D.       The Sufficiency of the Evidence of Obstruction of Justice

 3            Spadoni claims that he is entitled to a judgment of acquittal on the charge of violating 18

 4   U.S.C. § 1503 because there was insufficient evidence to support the jury’s finding that he knew

 5   his actions were likely to affect the grand jury proceedings. He bases this argument on United

 6   States v. Aguilar, 515 U.S. 593 (1995), where the Supreme Court held that § 1503’s intent

 7   element incorporates a requirement that the defendant have “knowledge that his actions are likely

 8   to affect the judicial proceeding” being obstructed. Id. at 599.14

 9            The Court in Aguilar derived this requirement from several decisions limiting the facially

10   broad language of the obstruction statute. Id. at 598-99. The provision at issue is § 1503’s

11   “omnibus clause,” which follows several clauses criminalizing endeavors to injure, intimidate or

12   influence grand or petit jurors or court officers. The omnibus clause contains a more general and

13   open-ended prohibition, punishing anyone who “corruptly or by threats or force, or by any

14   threatening letter or communication, influences, obstructs, or impedes, or endeavors to influence,

15   obstruct, or impede, the due administration of justice.” § 1503. Wary of the breadth of this

              13
                         Spadoni argues that the impeaching effect of the proffer notes might have led the jury to discredit
     Silvester’s testimony in its entirety, including his statements regarding the obstruction of justice charge, and thus that
     the suppressed evidence raises a reasonable probability that the jury would not have convicted Spadoni of
     obstruction of justice. We disagree. Even if the suppressed notes had an impeaching effect so strong as to call into
     question Silvester’s testimony on other matters, the government’s evidence of Spadoni’s obstruction of justice was
     overwhelming. In light of the forensic examiner’s detailed testimony regarding the suspicious timing of the deletion
     of relevant files from Spadoni’s laptop using Destroy-It! software, and its corroboration with Trevisani’s testimony
     about Spadoni’s mention of Destroy-It! as software to be used in order to “hide something,” Trial Tr. vol. 7, 217, we
     do not think that the suppression of Agent Urso’s notes raises a reasonable probability that the verdict on the
     obstruction of justice count would have been different.

              14
                        Prior to Aguilar, we had noted that “destroying documents in anticipation of a subpoena can
     constitute obstruction.” United States v. Ruggiero, 934 F.2d 440, 450 (2d Cir. 1991). Spadoni argues that we must
     reevaluate this precedent in light of Aguilar.

                                                                26
 1   language in a criminal prohibition, courts have limited its scope in several ways.

 2           In United States v. Pettibone, 148 U.S. 197 (1893), the Supreme Court imposed a

 3   requirement that a judicial proceeding actually exist, and that the defendant know or have notice

 4   of its existence. Id. at 206-07. The Court in Pettibone deemed it impossible to intend to obstruct

 5   a proceeding of which one was unaware or had no notice, and thus inferred the requirement of

 6   knowledge from the statute’s corrupt intent element. Id.

 7           Additionally, several courts of appeals, apparently in order to confine § 1503’s

 8   application to sufficiently harmful conduct, imposed a “nexus” requirement, under which the

 9   defendant’s conduct must be such “‘that its natural and probable effect would be the interference

10   with the due administration of justice.’” United States v. Wood, 6 F.3d 692, 695 (10th Cir. 1993)

11   (quoting United States v. Thomas, 916 F.2d 647, 651 (11th Cir. 1990)). Of course, the

12   government was not required to prove that conduct with the natural and probable effect of

13   obstructing justice actually succeeded in doing so in order to prove an endeavor to obstruct

14   justice under § 1503. Wood, 6 F.3d at 695-96 & n.4; Thomas, 916 F.2d at 651.

15           In Aguilar, the Supreme Court adopted this “nexus” requirement with a slight

16   modification. 515 U.S. at 600. It applied Pettibone’s requirement of knowledge15 not just to the

17   existence of a proceeding, but to the likelihood that the defendant’s actions would affect it,

18   holding that “as in Pettibone, if the defendant lacks knowledge that his actions are likely to affect

19   the judicial proceeding, he lacks the requisite intent to obstruct.” Aguilar, 515 U.S. at 599.16 The

             15
                      It did not, however, allow a conviction based on mere notice, as opposed to knowledge.

             16
                       The Court also noted, puzzlingly, that the “natural and probable effect” requirement was
     equivalent both to the requirement that the defendant intend to influence judicial or grand jury proceedings as
     opposed to ancillary proceedings, Aguilar, 515 U.S. at 599 (citing United States v. Brown, 688 F.2d 596, 598 (9th

                                                             27
 1   Court apparently used the word “likely” to stand in for the requirement that the action have the

 2   natural and probable effect of obstructing the judicial proceeding. See Aguilar, 515 U.S. at 613

 3   (Scalia, J., concurring in part and dissenting in part) (adopting this interpretation of the majority

 4   opinion).

 5            However, the facts of Aguilar appeared to complicate its holding that a defendant must

 6   have knowledge that his or her action is likely to affect the proceeding. The government

 7   presented evidence that Robert Aguilar made false statements to an FBI agent regarding an

 8   unauthorized disclosure of a wiretap, and that he did so while aware that a grand jury was

 9   investigating the same matter. Id. at 596-97. The government’s theory was that the defendant

10   endeavored to obstruct the grand jury proceeding by lying to the agent with the intent that the

11   agent communicate his false statements to the grand jury. Id. at 600-01. The Supreme Court

12   found the evidence insufficient to show that Aguilar “knew that his false statement would be

13   provided to the grand jury” and thus reversed his § 1503 conviction. Id. at 601. On its face, this

     Cir. 1982)), and also to the more general requirement that the charged act “have a relationship in time, causation, or
     logic with the judicial proceedings.” Aguilar, 515 U.S. at 599 (citing Wood 6 F.3d at 696, United States v. Walasek,
     527 F.2d 676, 679 & n.12 (3d Cir. 1975)).
                        The equivalences the Court perceived do not have a great deal of practical significance. An
     instruction solely on the requirement that the defendant intend to influence judicial or grand jury proceedings as
     opposed to ancillary proceedings, without stating that the defendant must know that his actions are likely to obstruct
     the proceedings, is insufficient to support a § 1503 conviction -- the jury in Aguilar certainly could have found that
     the defendant intended to influence the grand jury proceeding, 515 U.S. at 613-14 (Scalia, J., concurring in part and
     dissenting in part). Similarly, an instruction stating only that the jury must find that the defendant’s act had “a
     relationship in time, causation or logic with the judicial proceedings,” id. at 599, without specifying that the
     defendant must know that his act is likely to obstruct the proceeding, is also insufficient to support a § 1503
     conviction. Any action has some relationship in time, causation or logic with judicial proceedings, and without
     specific guidance on what that relationship must be, a jury may vote to convict without finding that a defendant knew
     that his action was likely to obstruct a judicial or grand jury proceeding.
                        Conversely, if the jury is instructed that a defendant, in order to violate § 1503’s omnibus clause,
     must know that his action was likely to obstruct a judicial or grand jury proceeding, there is no need to instruct the
     jury that the defendant’s act must have a relationship in time, causation or logic with the judicial proceedings. The
     jury must, however, be instructed that the defendant cannot be convicted if he does not intend to obstruct the judicial
     or grand jury proceedings.

                                                               28
 1   statement seems in tension with the standard that the Court announced, which requires only that a

 2   defendant know that her actions would be likely to affect the proceeding, not that she know that

 3   her actions would have that effect.

 4            Later in the opinion, however, the Court indicated that the operative question was

 5   whether Aguilar knew that his false statement was likely to be provided to the grand jury, and

 6   that the Court’s reference to whether Aguilar knew that his statement “would be provided” was

 7   an imprecise shorthand. The Court posited several situations where a defendant would violate §

 8   1503 by knowing that his false statements were likely to be provided to the grand jury despite the

 9   fact that the statements were not actually provided to the grand jury, such as where a defendant

10   lies to “a subpoenaed witness who is ultimately not called to testify, or who testifies but does not

11   transmit the defendant’s version of the story.” Aguilar, 515 U.S. at 602. In indicating that a

12   defendant could be culpable where false statements were not in fact provided to the grand jury,

13   the Court made clear that the inquiry is whether the defendant knew his statements were likely to

14   be presented to the grand jury, not whether he knew they would be presented.17

15            Spadoni argues that his conduct was directly analogous to Aguilar’s. Destroying a

              17
                         W e note that Aguilar seems to allow the term “likely,” perhaps because it is used interchangeably
     with the natural and probable consequence formulation, to encompass plans where success reasonably appears to be
     likely but is in fact impossible. A witness who is known to be subpoenaed to testify before the grand jury but who
     secretly has no intention of relating the defendant’s version of the story appears to still qualify as “likely” to pass
     along the defendant’s false statements for the purposes of the defendant’s mental state. See id. (“W ere a defendant
     with the requisite intent to lie to a subpoenaed witness . . . who testifies but does not transmit the defendant’s version
     of the story, the defendant has endeavored to obstruct, but has not actually obstructed, justice. Under our approach,
     a jury could find such defendant guilty.”). In using the term “likely” or “natural and probable consequence” in this
     way, the Court simply follows the longstanding rule that apart from the nonexistence of a judicial proceeding, see
     Pettibone, 148 U.S. at 207 (finding that predecessor to § 1503 could not be violated if no judicial proceedings
     existed to be obstructed); United States v. Reed, 773 F.2d 477, 485 (2d Cir. 1985) (“[T]he existence of an ongoing
     proceeding is an element of a § 1503 violation . . . .”), impossibility is not a defense to obstruction of justice, see
     Osborn v. United States, 385 U.S. 323, 333 (1966) (affirming § 1503 conviction where the defendant passed bribe
     money to a government cooperator who had no intention of delivering it to the target juror).

                                                                29
 1   document does not in fact affect a grand jury proceeding if the grand jury never requests the

 2   document. While Spadoni deleted several documents from his company laptop, at no time did he

 3   delete a document for which there was an outstanding subpoena. Just as there was insufficient

 4   evidence to prove that Aguilar knew his false statements would later be communicated to the

 5   grand jury (or, as indicated above, were likely to be communicated to the grand jury), so, goes the

 6   argument, there is insufficient evidence to prove that Spadoni knew the documents he deleted

 7   would later be, or were likely later to be, requested by the grand jury.

 8          Spadoni’s argument ignores a key difference between the issuance of a grand jury

 9   subpoena duces tecum seeking the production of documents and the questioning of a subject by

10   an investigating agent. Grand jury subpoenas duces tecum are customarily employed to gather

11   information and make it available to the investigative team of agents and prosecutors so that it

12   can be digested and sifted for pertinent matter. Before the subpoenas are issued, the government

13   often does not have at its disposal enough information to determine precisely what information

14   will be relevant. Cf. United States v. R. Enters., Inc., 498 U.S. 292, 297 (1991) (“‘[T]he identity

15   of the offender, and the precise nature of the offense, if there be one, normally are developed at

16   the conclusion of the grand jury’s labors, not at the beginning.’” (quoting Blair v. United States,

17   250 U.S. 273, 282 (1919))). Indeed, “[t]he function of the grand jury is to inquire into all

18   information that might possibly bear on its investigation until it has identified an offense or has

19   satisfied itself that none has occurred. As a necessary consequence of its investigatory function,

20   the grand jury paints with a broad brush.” Id. at 297 (internal citation and quotation marks

21   omitted).

22          Accordingly, subpoenas duces tecum are often drawn broadly, sweeping up both

                                                      30
 1   documents that may prove decisive and documents that turn out not to be. This practice is

 2   designed to make it unlikely that a relevant document will escape the grand jury’s notice, and it is

 3   generally effective. Destruction of a relevant document is therefore likely to impact the grand

 4   jury’s deliberations. Cf. Aguilar, 515 U.S. at 601 (“delivery of false documents” to the grand

 5   jury would be obstruction of justice).

 6          By contrast, an investigating agent collecting statements from witnesses (or even, as in

 7   Aguilar, from a suspect) does not always act as “an arm of the grand jury,” and “what use will be

 8   made of false testimony given to an investigating agent who has not been subpoenaed or

 9   otherwise directed to appear before the grand jury is . . . speculative.” Id. 515 U.S. at 600-01.

10          This context provides a crucial distinction between Aguilar’s conduct and Spadoni’s.

11   The inference that Aguilar’s statements to the agent would be presented to the grand jury was not

12   strong. The statements were not obtained by grand jury subpoena, and statements made to

13   investigating agents are not communicated to grand juries as a matter of course. By contrast, the

14   inference that the grand jury would issue a subpoena for the Thiesfield and Stack contracts was

15   quite strong, perhaps inescapable. The government produced evidence suggesting Spadoni’s

16   awareness of the comprehensive nature of the subpoenas duces tecum typically issued in federal

17   grand jury investigations. The jury heard evidence that Triumph’s attorneys anticipated further

18   subpoenas, Trial Tr. vol. 5, 179-80; that Spadoni had received advice from a former prosecutor

19   indicating that the grand jury would be likely to inspect the data contained on his laptop, id. at

20   180-81; that Spadoni stated his belief that federal investigations are “very comprehensive and

21   thorough,” id. at 194; and that Spadoni asked Silvester to destroy copies of a different contract,

22   id. at 191-93.

                                                      31
 1           The Stack and Thiesfield contracts were not peripheral documents; they were at the very

 2   core of the transaction the government was investigating. The jury could have concluded that

 3   Spadoni was aware that further subpoenas covering a broad range of documents would issue, and

 4   that he knew that it was likely that the Stack and Thiesfield contracts would be requested.

 5   Accordingly, Spadoni’s conviction for obstruction of justice, based on his destruction of those

 6   documents in his computer files, was supported by sufficient evidence.

 7   E.      The Jury Instructions Regarding Obstruction of Justice

 8           Spadoni argues that even if the evidence was sufficient to support his conviction, the

 9   district court’s instructions allowed the jury to convict him on a theory inconsistent with

10   Aguilar’s mens rea requirement. He challenges the instruction that in order to convict, the jury

11   had to “find that in the defendant’s mind, his or its conduct had the natural and probable effect of

12   obstructing or interfering with the grand jury proceeding.” Trial Tr. vol. 16, 123. The district

13   court rejected the defendant’s request to insert the words “he knew that” after “in the defendant’s

14   mind.” Def.’s Exceptions to Jury Instructions 7. Spadoni argues that the instruction as given

15   allowed the jury to convict him if it merely found that he had a belief or impression that his

16   conduct was likely to affect the grand jury investigation, a mental state that falls short of § 1503’s

17   requirements. We are not persuaded.

18           Courts have long struggled to determine, in the § 1503 context and elsewhere, precisely

19   what level of certainty is necessary to constitute knowledge. The issue has not been fully

20   resolved,18 but Aguilar makes clear that § 1503 is not violated if the defendant merely has the

             18
                       See United States v. Solow, 138 F. Supp. 812, 816 & n.14 (S.D.N.Y. 1956) (finding that belief
     and reasonable grounds to believe that destroyed documents would be requested by a grand jury sufficed for § 1503
     conviction); compare United States v. Golomb, 811 F.2d 787, 792 (2d Cir. 1987) (“Knowledge and belief are very

                                                            32
 1   impression that his conduct will have the natural and probable effect of obstructing justice. See

 2   Aguilar, 515 U.S. at 601-02. The jury in that case heard evidence that the agent had told Aguilar

 3   that a grand jury would be hearing evidence about the investigation, 515 U.S. at 600, and Aguilar

 4   himself testified that, at the end of the interview, it was his “impression” that his remarks would

 5   be conveyed to the grand jury. Id. at 614 (Scalia, J., concurring in part and dissenting in part).

 6   The jury could reasonably have inferred that Aguilar, at the time he made false statements, had

 7   the impression that those statements would be conveyed to the grand jury. Yet the Supreme

 8   Court found the evidence insufficient to support a finding that he had the requisite mental state

 9   for a § 1503 conviction. That element necessarily requires more than a showing that the

10   defendant merely had the impression that his conduct would have the natural and probable effect

11   of obstructing justice.

12            In this case, the district court instructed the jury that the government must prove that “in

13   the defendant’s mind, his or its conduct had the natural and probable effect of obstructing or

14   interfering with the grand jury proceeding.” Trial Tr. vol. 16, 123. The court’s language was

15   taken from our opinion in United States v. Schwarz, 283 F.3d 76 (2d Cir. 2006), where we

16   explained that under Aguilar, the conduct offered to prove § 1503’s intent element “must be

17   conduct that is directed at the court or grand jury and that, in the defendant’s mind, has the

18   ‘natural and probable effect’ of obstructing or interfering with that entity.” Schwarz, 283 F.3d at

     different mental states; knowledge implies a much higher degree of certainty.”), with United States v. Coté, 504 F.3d
     682, 688 & n.7 (7th Cir. 2007) (distinguishing Golomb as a case dealing with completed offenses and concluding
     that the defendant in a prosecution for a criminal attempt articulated “no discernable difference between ‘belief’ and
     ‘knowledge’” in his case); cf. Model Penal Code § 2.02(7) (Proposed Official Draft 1962) (“When knowledge of the
     existence of a particular fact is an element of an offense, such knowledge is established if a person is aware of a high
     probability of its existence, unless he actually believes that it does not exist.”).

                                                                  33
 1   109 (quoting Aguilar, 515 U.S. at 599). We conclude that it sufficiently conveyed the high

 2   degree of certainty § 1503 requires. The district court did not tell the jury that § 1503 required a

 3   finding that in Spadoni’s mind, his conduct might have had the natural and probable effect of

 4   obstructing justice, but rather a finding that in his mind, his conduct did have the natural and

 5   probable effect of obstructing justice. That is, the instruction adequately conveyed that Spadoni

 6   must be certain enough of his conduct’s natural and probable obstructive effect that, to him, the

 7   effect was a fact, not a mere possibility. The district court’s charge thus imposed on the

 8   government a burden substantially more demanding than merely proving that Spadoni had the

 9   impression that his conduct would have the natural and probable effect of obstructing justice, a

10   formulation that connotes a highly tentative belief. See, e.g., American Heritage Dictionary of

11   the English Language (4th ed. 2000), available at http://www.bartleby.com/61/57/I0065700.html

12   (defining “impression” as, inter alia, “2. A vague notion, remembrance, or belief”). Without

13   resolving the difficult question of precisely what degree of certainty amounts to knowledge under

14   § 1503, we can say that the formulation at issue here sufficed to convey the requisite certainty.

15          It is true that our reference in Schwarz to what was “in the defendant’s mind,” which was

16   reproduced by the district court in the challenged instruction, could have made it clearer that the

17   defendant’s subjective belief has to amount to knowledge. Compare Schwarz, 283 F.3d at 109

18   (stating that the conduct evincing the defendant’s specific intent “must be conduct that is directed

19   at the court or grand jury and that, in the defendant’s mind, has the natural and probable effect of

20   interfering with that entity” (internal quotation marks omitted), with id. (“‘[I]f the defendant

21   lacks knowledge that his actions are likely to affect the judicial proceeding, he lacks the requisite

22   intent to obstruct.’” (emphasis added) (quoting Aguilar, 515 U.S. at 599)). If the case had

                                                      34
 1   involved a claimed error in the jury charge, as opposed to a sufficiency challenge to Schwarz’s §

 2   1503 conviction, we might have addressed more squarely the issue before us here. In any event,

 3   though the district court’s use of our language from Schwarz was understandable, we believe the

 4   better course in future cases would be for courts to make it explicit that to violate § 1503’s

 5   omnibus clause, a defendant must know that her conduct has the natural and probable effect of

 6   obstructing the judicial or grand jury proceeding in question (or, what amounts to the same thing,

 7   that the defendant must know that her conduct is likely to obstruct the proceeding).

 8            However, a jury instruction need only adequately -- not perfectly -- instruct the jury on the

 9   applicable legal standard. See, e.g., United States v. Naiman, 211 F.3d 40, 51 (2d Cir. 2000)

10   (“‘A jury instruction is erroneous if it misleads the jury as to the correct legal standard or does

11   not adequately inform the jury on the law.’” (quoting United States v. Walsh, 194 F.3d 37, 52 (2d

12   Cir. 1999))). The fact that a jury could conceivably misinterpret an instruction as to the requisite

13   state of mind does not render the instruction erroneous. See, e.g., Victor v. Nebraska, 511 U.S. 1,

14   6 (1994) (“[T]he proper inquiry is not whether the instruction ‘could have’ been applied in an

15   unconstitutional manner, but whether there is a reasonable likelihood that the jury did so apply

16   it.” (citing Estelle v. McGuire, 502 U.S. 62, 72 & n.4 (1991)); see also Jones v. United States,

17   527 U.S. 373, 390 & n.9 (1999) (similar). Thus, while we encourage district courts in the future

18   to make clear that the required mental state is knowledge that the defendant’s conduct had the

19   natural and probable effect of obstructing justice, we do not find that the instruction as given was

20   erroneous.19

              19
                        Our conclusion in this regard is further supported by our examination of how the case was actually
     presented to the jury at trial. In summation, the prosecutor explicitly stated that Spadoni could not be convicted
     unless he knew that his conduct had the natural and probable effect of obstructing the proceeding. Trial Tr. vol. 14,

                                                              35
1            Accordingly, Spadoni is not entitled to a new trial on the obstruction of justice charge.

2                                                   CONCLUSION

3            For the foregoing reasons, we affirm Spadoni’s conviction on Count 24, but reverse the

4   judgment of the district court and remand for a new trial on Counts 1, 2, and 19-23. Because we

5   cannot be certain that the 36-month concurrent sentence on Count 24 was not affected by the

6   convictions that we have reversed, the sentence on Count 24 is vacated and the case is remanded

7   for resentencing on that count.

    49 (“[D]id he corruptly endeavor to obstruct the Grand Jury? That is, did he know that his contact -- conduct, excuse
    me, would have the natural and probable effect of interfering with the Grand Jury?”). Spadoni’s counsel conveyed
    the same standard. Id. at 195 (“He has to know that what he’s doing has the natural and probable effect of
    obstructing the Grand Jury.”). Under the circumstances, the risk that the jury would misunderstand the district
    court’s instruction was negligible.

                                                             36