In United States v. Pugh, No. 17-1889 (2d Cir. Dec. 10, 2019, as amended) (Calabresi, Droney, Underhill, by designation), the Second Circuit affirmed a defendant’s convictions for attempting to provide material support to a foreign terrorist organization and obstruction of justice but vacated the resulting sentence on procedural reasonableness grounds.

The defendant, Tairod Nathan Webster Pugh, was a U.S. citizen and Air Force veteran who began researching and downloading propaganda materials promulgated by the Islamic State of Iraq and the Levant (“ISIL” or “ISIS”), and who was denied entry into Turkey and detained in Egypt on suspicion of attempting to travel through Turkey to enter Syria and join ISIS. While detained in Egypt, Pugh attempted to destroy or destroyed some of the electronic devices he had in his possession, which were later determined to contain information relating to ISIS. Pugh was ultimately convicted of attempting to support a foreign terrorist organization, see 18 U.S.C. § 2339B(a)(1), and obstruction and attempted obstruction of an official proceeding, see 18 U.S.C. § 1512(c)(1) and (c)(2). He was sentenced to the maximum sentence on each count, to run consecutively, which amounted to a total effective sentence of 420 months.

On appeal, Pugh challenged (1) the district court’s evidentiary ruling admitting an inculpatory letter that Pugh had purportedly written to his wife over Pugh’s marital privilege objection; (2) the sufficiency of the evidence underlying his convictions; and (3) the procedural and substantive reasonableness of his sentence.

As to the admission of the letter, the Second Circuit found no error in the district court’s determination that there was “‘no evidence that Pugh intended the letter to be a communication’ because there was ‘no evidence that [he] intended to send the draft’.” In support of that ruling, the panel noted that the evidence showed that Pugh and his wife communicated exclusively through Facebook Messenger with the assistance of translators, and that the document in question was saved in a different format and had not been translated.

The Second Circuit rejected Pugh’s sufficiency challenge to each of his convictions. The Court held that there was sufficient evidence for a reasonable jury to find that Pugh had taken a “substantial step” in furtherance of his intended crime of attempting to provide material support to a foreign terrorist organization. The Court pointed to evidence recovered from Pugh’s electronic devices reflecting “ISIS propaganda videos and materials, as well as research into ISIS’ control of border crossings between Turkey and Syria,” and to testimony that Pugh was traveling with a “tactical backpack” filled with materials that would have been helpful to him in traveling to the Syrian border but that would not have been consistent with his purported legitimate reasons for being in Turkey. Affirming the obstruction of justice conviction, the Court highlighted Pugh’s destruction of documents and held that there was a sufficient “nexus” between Pugh’s destruction of materials and a future “official proceeding” in the United States because it was “reasonably foreseeable” to him when he was denied entry to Turkey and detained in Egypt that he would be prosecuted in the U.S. for his efforts to join ISIS.

The Court found persuasive, however, Pugh’s contention that his sentence was procedurally unreasonable because the district court failed to adequately “state in open court the reasons for its imposition of the particular sentence” it imposed on him. 18 U.S.C. § 3553(c). In vacating Pugh’s sentence on this basis, the Second Circuit noted that “[g]reater particularity in the reasons for a sentence is necessary . . . when the sentence reflects a more fulsome exercise of discretion,” and it determined that such discretion had been exercised by the district court in imposing a sentence at the top of the Guidelines range on each count, to run consecutively. The Court then held that the district judge’s statement of reasons did not meet this heightened standard because the “vast majority” of the district judge’s comments “relate[d] to Pugh’s guilt rather than to an appropriate sentence,” and because the district court did not explain “why a sentence equal to the statutory maximum on one [of the] count[s] on which Pugh was convicted did] not produce a sufficient sentence within the meaning of 18 U.S.C. § 3553(a).” The Court remanded for resentencing to afford the district court another opportunity to explain the reasons underlying the sentence, and did not reach the question of whether Pugh’s effective sentence of 420 months was substantively unreasonable.

The panel’s decision was accompanied by a forceful concurrence by Judge Calabresi “emphasiz[ing] the risks posed by the crime of obstruction of justice . . . as it has evolved.” Judge Calabresi noted that Pugh “illustrates how dangerously far 18 U.S.C. § 1512(c) now extends,” as the “government was able to take what is already a very serious crime—attempting to provide material support to a foreign terrorist organization—and . . . bring an obstruction charge that more than doubled the maximum sentence otherwise available.” Judge Calabresi expressed doubt as to whether it was “justifiable . . . to turn [Pugh’s] 15-year sentence into a 35-year one” where “there was no evidence to suggest that the [materials Pugh] deleted . . . contained information that was valuable or significant in itself or for ISIS.” To Judge Calabresi, Pugh is emblematic of the “expansive[]” application of the federal obstruction of justice statute which, “arguabl[y,] . . . was never intended to be used so broadly.” Judge Calabresi ended his concurrence with a prescription to mitigate the potential overbreadth and severity of obstruction of justice prosecutions, calling for a sentence for that offense to “reflect the severity of the obstruction of justice, in the context of a particular underlying crime, and not prosecutorial or judicial dissatisfaction with the limits Congress placed on the gravity of that underlying crime.”

Pugh is a fascinating case in two respects. First, it seems to show underlying concerns about the substantive reasonableness of a sentence providing context for a procedural reasonableness determination. As the Pugh Court itself noted, where a district court exercises its discretion to impose a longer sentence, the appellate court will apply a more exacting review to find “greater particularity” in the district court’s statement of reasons justifying that longer sentence. In this way, heightened 3553(c) review allows a reviewing court to mitigate some of the harshness associated with a particularly lengthy sentence without creating precedent that could be read to expand the scope of the substantive reasonableness doctrine.

Second, Judge Calabresi’s concurrence provides a timely note of caution in a climate where prosecutors are increasingly relying on obstruction of justice charges. In some respects, Judge Calabresi’s prescription—applying a more searching review to focus on the “severity of the obstruction of justice”—mirrors the “greater particularity” 3553(c) approach to reviewing particularly lengthy sentences. Both call for a heightened degree of judicial review under existing statutory frameworks. And both could be seen, perhaps, as implicit reminders to other actors in the criminal justice system—district judges on the one hand, and prosecutors on the other—to bear in mind the Circuit’s underlying concerns for the rights of defendants.

Judge Calabresi is also not alone in expressing concern about the over-use of the federal obstruction statutes. In Yates v. United States, 135 S. Ct. 1074 (2015), the Supreme Court rejected the Department of Justice’s effort to apply 18 U.S.C. § 1519 to the destruction of physical evidence when its wording indicated that Congress only intended for the statute to reach the destruction of documents. Then in Marinello v. United States, 138 S. Ct. 1101 (2018), the Supreme Court narrowed the reach of the “omnibus” clause of 26 U.S.C. § 7212(a), in order to prevent the statute from reaching conduct with no relationship to a specific proceeding. In both instances, the Supreme Court prevented expansive applications of the obstruction statutes urged by prosecutors. As Judge Calabresi reminds us, the justness of our criminal justice system depends in part on the assumption that prosecutors and judges will exercise their discretion in charging and sentencing, respectively, with a focus on the severity of the conduct in light of the particular circumstances, and will not allow those weighty decisions to be informed by “dissatisfaction” with the reach of, or punishment associated with, a given statute.