United States v. Singer

• Decision Date: 26 June 2020
• Docket Number: No. 18-14294,18-14294
• Parties: UNITED STATES of America, Plaintiff - Appellee, v. Bryan Evan SINGER, a.k.a. Bryan Blackhart, Defendant - Appellant.
• Court: U.S. Court of Appeals — Eleventh Circuit

963 F.3d 1144

UNITED STATES of America, Plaintiff - Appellee,

v.Bryan Evan SINGER, a.k.a. Bryan Blackhart, Defendant - Appellant.

No. 18-14294

United States Court of Appeals, Eleventh Circuit.

June 26, 2020

Daniel Matzkin, Jonathan Colan, Emily M. Smachetti, U.S. Attorney Service - SFL, Miami, FL, for Plaintiff-Appellee.

Craig Joseph Trocino, Miami Law Innocence Clinic, Coral Gables, FL, Roger Cabrera, Roger Cabrera, PA, Miami, FL, for Defendant-Appellant.

Before ROSENBAUM, JILL PRYOR, and BRANCH, Circuit Judges.

ROSENBAUM, Circuit Judge:

Fidel Castro came to power in Cuba in 1959, after overthrowing Fulgencio Batista.¹ The following year, on October 19, 1960, the United States imposed the first trade embargo on Cuba.² Though the contours of that embargo have changed over the sixty years since then, significant parts of it remain in effect through today.³ This case concerns Defendant-Appellant Bryan Singer's conviction for attempting to violate an aspect of that embargo that is currently embodied in the International Emergency Economic Powers Act and regulations promulgated in accordance with that Act—more specifically, a prohibition on exporting to Cuba technology that can be used for encryption capabilities and can affect United States national security and anti-terrorism efforts.

Singer argues on appeal that the government presented insufficient evidence to support his conviction for attempting to export 303 Ubiquiti NanoStation M2 Network Modems⁴ ("NanoStations") to Cuba without a license. Raising an issue of first impression, he contends that the government was required to prove he knew of the facts that made the NanoStations subject to prohibitions on export to Cuba without a license. We agree. But we conclude that the jury instructions the district court gave correctly explained the level of knowledge required to convict, and the evidence admitted at trial established Singer's knowledge beyond a reasonable doubt.

We also reject Singer's claim that the evidence did not sufficiently establish that he took a substantial step towards exporting the NanoStations in violation of the law. So we affirm Singer's conviction for attempting to export NanoStations to Cuba without a license.

Singer's challenge to the district court's application of the two-point obstruction-of-justice Sentencing Guidelines enhancement fares no better. After careful consideration, with the benefit of oral argument, we therefore affirm Singer's conviction and sentence.

I.

As we have noted, Singer was convicted of attempting to export NanoStations from the United States to Cuba. The United States government has designated NanoStations as having the potential to affect national security and anti-terrorism efforts. Singer was also convicted of lying to a special agent of the Department of Homeland Security who was attempting to ensure compliance with the laws regulating travel and exports to Cuba. So before we discuss the facts of Singer's case, it is helpful to review the governing legal background. We begin with a description of the International Emergency Economic Powers Act ("IEEPA"), codified at 50 U.S.C. §§ 1701 - 07, and relevant regulations promulgated in accordance with it. Then we review the relevant rules for travel and exportation of items to Cuba.

A. The International Emergency Economic Powers Act and the Export Administration Regulation at Issue Here

This case deals in part with the IEEPA and regulations promulgated under it. The IEEPA addresses the President of the United States's authority to regulate international economic transactions during wars or national emergencies. See 50 U.S.C. §§ 1701 - 02. Under the IEEPA, the President may declare a national emergency through executive orders that have the full force and effect of law.

The IEEPA also authorizes the President to issue regulations governing exports. See id. §§ 1702(a)(1)(B), 1704. Originally, though, the Export Administration Act, 50 App. U.S.C. §§ 4601-23, empowered the Department of Commerce to promulgate regulations to implement the Export Administration Act, which regulated the exportation of goods, technology, and software from the United States. The Department of Commerce used that authority to issue the Export Administration Regulations, 15 C.F.R. pts. 730-774 (the "EAR"), which imposed certain restrictions on the exportation of goods, technology, and software from the United States. See 15 C.F.R. § 730.2.

When the Export Administration Act lapsed in 2001, President George W. Bush used his authority under the IEEPA to issue Executive Order 13222. Executive Order 13222 declared that the expiration of the Export Administration Act created a national emergency resulting in an "unusual and extraordinary threat to the national security, foreign policy, and economy of the United States" in the form of, in relevant part, "the unrestricted access of foreign parties to U.S. goods and technology." Exec. Order 13222, 66 Fed. Reg. 44025 (Aug. 17, 2001). To address this national emergency, under the IEEPA, President Bush ordered the EAR's provisions to remain in full force and effect, despite the expiration of the Export Administration Act. See id. at § 2.

Since President Bush issued Executive Order 13222, President Bush and those Presidents who have followed him have released annual Executive Notices extending the national emergency declared in Executive Order 13222 from that time through now. See , e.g. , https://obamawhitehouse.archives.gov/the-press-office/2016/08/04/notice-continuation-national-emergency-respect-export-control (last visited June 26, 2020); 82 Fed. Reg. 39005 (Aug. 16, 2017) ; 83 Fed. Reg. 39871 (Aug. 13, 2018) ; 84 Fed. Reg. 41881 (Aug. 15, 2019).

The IEEPA makes it "unlawful for a person to violate, attempt to violate, conspire to violate, or cause a violation of any license, order, regulation, or prohibition issued under [the IEEPA]." 50 U.S.C. § 1705(a). Since the President renewed the EAR under the IEEPA, § 1705(a) makes it unlawful for a person to violate any regulation of the EAR. And any "person who willfully commits [or] willfully attempts to commit" a violation under § 1705(a) is guilty of a federal felony. Id. at § 1705(c).

As relevant here, the EAR restricts the export of items that could make a significant contribution to the military potential of other nations or that could be detrimental to the foreign policy or national security of the United States. In furtherance of protecting the national security, the EAR imposes licensing and other requirements for the lawful exportation from the United States of items subject to the EAR, and for their lawful re-exportation from one foreign destination to another.

The Department of Commerce identifies the most sensitive items subject to EAR controls on the Commerce Control List (or the "List"), published at 15 C.F.R. Part 774, Supp. No. 1. It categorizes items on the List by Export Control Classification Number ("ECCN"), each of which is subject to export-control requirements, depending on the destination, end use, and end user of the item. ECCN 5A002 covers "[i]nformation security" systems, equipment, and components. See 15 C.F.R. pt. 774, Supp. No. 1, Cat. 5, Part 2, A.I. This category is subject to the controls of the EAR because it includes national-security, anti-terrorism, and encryption items. Id.

As relevant here, items that fall into ECCN 5A002.a.1 require a license for exportation to Cuba. See id. ; 15 C.F.R. §§ 746.1(a)(1), 746.2(a). Because ECCN 5A002.a.1 includes NanoStations within its parameters, NanoStations may not be exported to Cuba without a license.

Besides obtaining a specific license authorizing exportation, a person seeking to ship products to Cuba must also file an Electronic Export Information through the Automated Export System. See 13 U.S.C. § 305(a)(1) ; 15 C.F.R. pt. 30 (Foreign Trade Regulations). This system "strengthens the U.S. government's ability to prevent the export of [prohibited] items to unauthorized destinations and/or end users because [it] aids in targeting, identifying, and when necessary confiscating suspicious or illegal shipments prior to exportation." 15 C.F.R. § 30.1(b). The Department of Homeland Security, Customs and Border Protection (the "CBP"), administers the Automated Export System.

B. Relevant Legal Framework for Exporting Items to Cuba

We now turn to the relevant law as it pertains to travel and exports to Cuba. On March 1, 1996, President William J. Clinton issued Proclamation 6867, entitled " Declaration of a National Emergency and Invocation of Emergency Authority Relating to the Regulation of the Anchorage and Movement of Vessels." 61 Fed. Reg. 8843. Among other things, Proclamation 6867 empowered the Secretary of Transportation (and later, the Secretary of Homeland Security) to promulgate rules and regulations governing the movement and inspection of vessels traveling from United States territorial waters into Cuban territorial waters. See id. § 1.

President George W. Bush expanded the scope of Proclamation 6867 when he issued Proclamation 7757 on February 26, 2004. 69 Fed. Reg. 9515. Among other things, in Proclamation 7757, President Bush reaffirmed the Secretary of Homeland Security's authority to promulgate rules and regulations controlling the movement and inspection of vessels from the United States territorial waters into Cuban territorial waters. See id. § 1.

In accordance with the authority afforded the Secretary of Homeland Security, the Department of Homeland Security promulgated 33 C.F.R. § 107.240, which provides that 33 C.F.R. Part 107, Subpart B, remains effective for the duration of the national emergency relating to Cuba and its attendant emergency authority, as declared in Proclamations 6867 and 7757. Among other regulations, 33 C.F.R. Part 107, Subpart B requires those leaving United States territorial waters headed for Cuban territorial waters to first obtain a written permit from the Coast Guard. See 33 C.F.R. § 107.215(a)....