Court Opinion

ID: 4544583
Source: CourtListenerOpinion
Date Created: 2020-06-26 17:00:32.704864+00
Date Added: 2024-06-11T12:49:30.956864
License: Public Domain

Case: 18-14294    Date Filed: 06/26/2020    Page: 1 of 46

                                                                         [PUBLISH]

             IN THE UNITED STATES COURT OF APPEALS

                     FOR THE ELEVENTH CIRCUIT
                       ________________________

                                No. 18-14294
                          ________________________

                  D.C. Docket No. 4:18-cr-10012-KMM-1

UNITED STATES OF AMERICA,

                                                 Plaintiff - Appellee,

versus

BRYAN EVAN SINGER,
a.k.a. Bryan Blackhart,

                                                 Defendant - Appellant.

                          ________________________

                Appeal from the United States District Court
                    for the Southern District of Florida
                      ________________________

                               (June 26, 2020)

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

ROSENBAUM, Circuit Judge:
                Case: 18-14294       Date Filed: 06/26/2020       Page: 2 of 46

       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 Modems 4 (“NanoStations”) to Cuba without a license. Raising an issue of

first impression, he contends that the government was required to prove he knew of

       1
           https://www.history.com/topics/cold-war/fidel-castro (last visited June 26, 2020).
       2
           https://time.com/4076438/us-cuba-embargo-1960/ (last visited June 26, 2020).
         3
           See https://www.history.com/this-day-in-history/full-us-cuba-embargo-is-announced
(last visited June 26, 2020).
         4
           According to government expert Michael Pender, a senior licensing officer with the U.S.
Department of Commerce’s Information Technology Controls Division, a NanoStation is a
communication device that uses 802.11 Wi-Fi to communicate over long distances of 1,000 feet
or more at high speeds typically for business use (not for home use). ECF No. 73 at 69.
NanoStations are subject to export control to Cuba because they are able to encrypt information.
Pender stated that products falling into the classification to which NanoStations are subject are
controlled for both national security and antiterrorism reasons, primarily because of concern that
criminals and foreign governments may use them to communicate in secret and without
interception by law enforcement or the National Security Agency. Id. at 70−71.
                                                2
                Case: 18-14294     Date Filed: 06/26/2020   Page: 3 of 46

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

                                            3
             Case: 18-14294     Date Filed: 06/26/2020   Page: 4 of 46

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.
                                         4
              Case: 18-14294     Date Filed: 06/26/2020    Page: 5 of 46

      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

                                          5
              Case: 18-14294    Date Filed: 06/26/2020   Page: 6 of 46

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.

                                         6
              Case: 18-14294    Date Filed: 06/26/2020   Page: 7 of 46

      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

                                         7
               Case: 18-14294      Date Filed: 06/26/2020   Page: 8 of 46

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). Individuals apply for this permit by submitting a written

application to the Coast Guard on an official form called the CG-3300. Id. §

107.220; ECF No. 73 at 32.

      The CG-3300 warns applicants, “Failure to obtain all of the appropriate

permits and licenses prior to travel to Cuba may result in felony prosecution . . . .”

                                            8
              Case: 18-14294     Date Filed: 06/26/2020    Page: 9 of 46

ECF No. 56-1 at 17. It further informs applicants that “[d]etailed information on the

U.S. embargo can be obtained from the U.S. Department of the Treasury, Office of

Foreign Assets Control (OFAC).” Id. Among other information, the form asks

applicants to state the purpose of the voyage in Cuban territorial seas. Id. The form

also requires the applicant to certify that the information provided “is true and

correct” and that he “understand[s] that willfully making a false, fictitious, or

fraudulent statement or concealing a material fact in this matter can result in”

imprisonment. Id.

      Significantly, though, a permit allowing a vessel to enter Cuban territorial

waters is not a license for an individual to travel to Cuba. See 33 C.F.R. §

107.220(c); see also ECF No. 73 at 33. Rather, to travel to Cuba from the United

States, a person must qualify for a general license or obtain a specific license. Title

31, Code of Federal Regulations, Part 515 sets forth several general licenses

covering certain types of travel to Cuba. Among these general-license provisions is

31 C.F.R. § 515.574, “[s]upport for the Cuban People.” In relevant part, this

provision allows those who satisfy its requirements to travel to, from, and within

Cuba. See 31 C.F.R. § 515.560(c). But the “[s]upport for the Cuban People” general

license does not authorize travel to Cuba for the purpose of exporting items from the

United States to Cuba, including the NanoStations, that fall into ECCN 5A002.a.1

on the Commerce Control List. See, generally, id.

                                          9
             Case: 18-14294     Date Filed: 06/26/2020      Page: 10 of 46

      Rather, as we noted in the section above on the IEEPA, “[a]ll the items on the

Commerce Control List . . . require a license to [export to] Cuba. 15 C.F.R. §

746.1(a)(1). As the regulations explain, though, “[m]ost items [on the List] requiring

a license [for export to Cuba] are subject to a general policy of denial.” Id.

Nevertheless, the regulations do provide a limited license exception for “[s]upport

for the Cuban People” where items controlled on the Commerce Control List are

involved.   Under that license exception, those items controlled for only anti-

terrorism reasons may be exported. 15 C.F.R. § 740.21(b). The “support for the

Cuban People” exception expressly prohibits exportation to Cuba where “any other

reason for control applies to the item.” Id.

      As we have noted, NanoStations fall within Commerce Control List ECCN

5A002.a.1. They are classified that way because they are considered “encryption

items” with national-security and anti-terrorism applications. Because they appear

on the List for reasons beyond anti-terrorism, we need not consider whether they

would otherwise qualify for a license exception for “support of the Cuban People”

since they cannot qualify for that exception, regardless.

                                      *****

      So to recap, to export NanoStations from the United States to Cuba by sea, a

person must have a valid permit to enter Cuban territorial waters and a valid license

authorizing the exportation of the items to Cuba. Neither a general license nor a

                                          10
             Case: 18-14294     Date Filed: 06/26/2020   Page: 11 of 46

license exception for “support for the Cuban People” will suffice. Exportation to

Cuba without a valid license authorizing that activity constitutes a violation of 50

U.S.C. § 1705(a) and, if willfully committed, is a felony, id. at § 1705(c). Finally,

besides a valid permit and a valid license, a person traveling to Cuba to export goods

must also file an Electronic Export Information through the Automated Export

System. See 13 U.S.C. § 305; 15 C.F.R. Part 30 (Foreign Trade Regulations).

                                         II.

      With this legal background in mind, we review the facts of this case.

      On May 1, 2017, Homeland Security Investigations (“HSI”) Special Agent

Todd Blyth received a dispatch advising him that a man was loading items onto a

boat at a marina in Key West and that the man was believed to be heading to Cuba.

ECF No. 58 at 9. Blyth went to the marina to check out the situation.

      There, he saw Bryan Singer, the man about whom he had received the tip.

ECF No. 58 at 9-10. Eight other men were also present and apparently assisted

Singer in loading several motorcycles and other equipment onto Singer’s vessel, La

Mala. Id. at 10.

      Blyth questioned Singer about his impending trip. In response, Singer told

Blyth that he was planning to transport the men, the motorcycles, and “other items

on his vessel to Cuba.” Id. Singer presented Blyth with an approved CG-3300,

                                         11
                Case: 18-14294   Date Filed: 06/26/2020   Page: 12 of 46

which Singer claimed (incorrectly) permitted him to transport the men and cargo to

Cuba. Id.

      Blyth reviewed the CG-3300. It did not indicate that Singer intended to export

goods to Cuba. See ECF No. 56-1 at 17. Rather, the CG-3300 purported to take

advantage of the general license for travel to Cuba for “support for the Cuban

People.” See id. In particular, the CG-3300 specified that the purpose of Singer’s

voyage was for “SUPPORT OF THE CUBAN PEOPLE, FOR A MOTORCYCLE

RALLY.” Id. Singer advised Blyth that the eight men present at the marina had

paid him $2,000 to transport them to Cuba. ECF No. 74 at 124-26, 127-28; ECF

No. 58 at 10.

      After reviewing the CG-3300, Blyth instructed Singer that the permit to enter

Cuban Territorial Seas did not allow him to leave for Cuba that day but instead

authorized him to depart the following day (May 2, 2017). ECF No. 58 at 10. Blyth

also informed Singer that he did not have a permit or license to export items and

that officers would return the following day to inspect his boat before it left for

Cuba. Id. at 10-12. Singer did not indicate that he was confused about the warnings.
Id. at 12. After the encounter with Blyth, the eight men took their motorcycles and

left, but the other items remained onboard the boat. ECF No. 74 at 74.

      The next day, May 2, 2017, Blyth and CBP officers, including Officer Scott

Hatfield, returned to the dock to conduct an outbound inspection of La Mala. ECF

                                          12
               Case: 18-14294        Date Filed: 06/26/2020      Page: 13 of 46

No. 58 at 12. Blyth later testified at Singer’s trial that Singer again said that he had

a valid CG-3300 and that he “wished to sail to Cuba.” Id. at 13. Singer, though,

asserted during trial that on May 2, he told Blyth he had canceled his trip to Cuba.

ECF No. 74 at 74.

       In any case, Blyth informed Singer that the officers wanted to conduct an

outbound inspection of the boat, and Singer agreed. Id. at 74-75; ECF No. 58 at 12.

During the process, the officers first asked Singer whether he had any items to

declare. ECF No. 58 at 13. Singer told them he had items in plain view inside the

boat’s main cabin. Then Singer produced receipts for those 4 or 5 items, none of

which required a specific license and the value of which totaled less than $2,500.5
Id. After the officers provided Singer another opportunity to declare any other

items, Singer again insisted that he did not have anything else to declare. Id.; ECF

No. 73 at 10; ECF No. 74 at 75. Singer then allowed law enforcement to search his

boat. ECF No. 58 at 13.

       During the search, Hatfield discovered that the queen-sized bed in the main

cabin of the boat was screwed down to the floor. ECF No. 73 at 13. Hatfield, who

had searched Singer’s boat on a prior occasion, remembered that the last time he

examined the bed, it was not screwed down to the floor, so he asked Singer about

       5
         A person seeking to export products that do not require a specific license must also file
an Electronic Export Information through the Automated Export System if the value of the goods
exceeds $2,500.00. ECF No. 73 at 140.
                                               13
             Case: 18-14294     Date Filed: 06/26/2020   Page: 14 of 46

it. Id. Singer responded that he had sealed the bed to the floor in Cuba because the

bed had been moving around too much with the ocean’s motion. Id.

      Hatfield removed the screws and lifted the bed. Id. Under the bed, Hatfield

discovered a hidden compartment that was “as full as it gets.” Id. at 15. Among the

items officers found in the compartment were 303 NanoStation devices and black

bags containing various things like motorcycle parts, link modems, and DirecTV

boxes. Id. at 13-18.

      According to Blyth and Hatfield, when Singer realized that the officers had

found the items beneath the bed, he apologized for fabricating the story that the bed

had been secured in Cuba. Id. at 18; ECF No. 58 at 22. Then Singer said he had

lied because he did not want United States law enforcement to find the items. ECF

No. 73 at 18; ECF No. 58 at 22. At trial, Singer disputed making part of this

statement. Instead, he testified that he told the officers he had hidden the items

because he did not want Cuban authorities to find them. ECF No. 74 at 72, 76-77.

After the officers discovered the items under the bed, they took custody of them as

evidence. ECF No. 58 at 22-23.

      Despite the May 2 encounter, Singer sailed to Cuba the following day, on May

3, 2017, arriving on May 4, 2017. ECF No. 74 at 78. Singer claimed that after

officers left the marina on May 2, other boaters in the marina convinced him to travel

to Cuba to drop off the items that had not been seized. Id. at 77-78. Singer made

                                         14
             Case: 18-14294     Date Filed: 06/26/2020   Page: 15 of 46

the trip and returned from Cuba to the United States by plane on May 5, 2017. Id.

at 78-79.

       Database checks later revealed that Singer had never applied for or obtained

an export license. ECF No. 74 at 21-22. Nor had he ever filed an Electronic Export

Information through the Automated Export System, as required. Id.

       When Singer arrived at the Fort Lauderdale International Airport on May 5,

2017, Special Agent Tina Stasulli Korb from the Department of Commerce’s

Bureau of Industry and Security’s Office of Export Enforcement met him. ECF No.

74 at 79-80. Korb had been alerted by law enforcement that Singer was flying into

the United States, returning from Cuba. ECF No. 74 at 9.

       When Korb encountered Singer at the airport on May 5, 2017, she interviewed

him and retrieved several documents from him, including a form from the Cuban

Ministry of Agriculture at the Hemingway Marina in Cuba, which was dated May

4, 2017. ECF No. 74 at 11-12; ECF No. 56-1 at 95. In that document, Singer

declared that he, as captain of La Mala, had been notified of certain Cuban

regulations. ECF No. 56-1 at 95. Singer did not dispute that he had, in fact, traveled

to Cuba on May 3, 2017. Singer also told Korb that all the NanoStations found in

the compartment on his boat during the May 2 outbound inspection were intended

for the passengers who were supposed to travel with him to Cuba. ECF No. 74 at

150.

                                         15
             Case: 18-14294    Date Filed: 06/26/2020   Page: 16 of 46

      Because he did not have a license to export the 303 NanoStations, Singer was

later charged with attempting to smuggle goods from the United States, “knowing

[them] to be intended for exportation contrary to law and regulations of the United

States, namely, [50 U.S.C. § 1705], and Section 746.2(a) of the Export

Administration Regulations,” in violation of 18 U.S.C. § 554(a). ECF No. 23 at 4;

ECF No. 74 at 21-22. Singer was also indicted for knowingly and willfully making

false statements to a Special Agent of HSI, in violation of 18 U.S.C. §1001(a)(2).

ECF No. 23 at 5.

      In addition to the evidence adduced at trial that we have already identified,

during his trial testimony, Singer admitted that he lied to law enforcement on May

2, 2017, when he stated that he did not have anything to declare besides the four or

five items in plain sight, because he knew about the electronics, including the

NanoStations, hidden under his bed. ECF No. 74 at 108-09. Singer also conceded

that he lied to law enforcement on May 2, 2017, when he stated that the bed in the

main cabin of the boat had been secured to the floor in Cuba. ECF No. 74 at 132.

      In addition, the government admitted into evidence at trial several CG-3300

applications Singer had submitted during 2016 and 2017. See ECF No. 56-1 at 17,

22, 27, 34, 42, 46, 53, 104, 106, 115, 117. Each of them stated that the purpose of

the anticipated voyage was “support [for] the Cuban People.” See id.

                                        16
             Case: 18-14294     Date Filed: 06/26/2020   Page: 17 of 46

      Singer moved for judgment of acquittal on the attempted-smuggling count at

the end of the government’s case in chief. ECF No. 74 at 57. He argued that he did

not take a “substantial step” towards committing the crime, since he canceled the

May 2 trip to Cuba. Id. The district court denied the motion, id. at 57-58, and the

jury later returned a verdict of guilty on both counts. ECF No. 105 at 32.

      Singer then renewed his motion for judgment of acquittal. ECF No. 60. The

district court again denied the motion. ECF No. 76. It later handed down a sentence

based on a Sentencing Guidelines range that included a two-level enhancement for

obstruction based on a finding that Singer had testified falsely during trial. ECF No.

97 at 26.

      Singer timely appealed his attempted-smuggling conviction and his overall

sentence. ECF No. 92.

                                        III.

A.     We find no error in Singer’s conviction for attempted smuggling

      1. Standard of Review

      We generally review de novo a district court’s denial of a motion for judgment

of acquittal. United States v. Seher, 562 F.3d 1344, 1364 (11th Cir. 2009). When

the motion is based on sufficiency of the evidence, as it is here, we will affirm if a

reasonable jury could find that the evidence demonstrates the defendant’s guilt

beyond a reasonable doubt. United States v. Rodriguez, 218 F.3d 1243, 1244 (11th

                                         17
               Case: 18-14294        Date Filed: 06/26/2020      Page: 18 of 46

Cir. 2000) (per curiam). In evaluating the sufficiency of the evidence, we view all

the evidence in the light most favorable to the verdict for the government, and we

make all reasonable inferences and credibility judgments in the government’s favor

as well. United States v. Grzybowicz, 747 F.3d 1296, 1304 (11th Cir. 2014); Seher,
562 F.3d at 1364.6

       2. The evidence sufficiently supports Singer’s conviction on the smuggling
          count

       Title 18, United States Code, Section 554(a), the statute under which Singer

was charged, makes it a crime to “knowingly export[] . . . or attempt[] to export . . .

any merchandise, article, or object contrary to any law or regulation of the United

States.” Here, Singer was charged with knowingly attempting to export hundreds of

NanoStations, contrary to 50 U.S.C. § 1705 and 15 C.F.R. § 746.2(a).

       To prove attempt, the government must show two things: that the defendant

(l) had “the specific intent to engage in the criminal conduct with which he is

charged; and (2) ha[d] taken a substantial step toward the commission of the offense

that strongly corroborates his criminal intent.” United States v. St. Hubert, 909 F.3d
335, 351 (11th Cir. 2018), cert. denied, 139 S. Ct. 1394 (2019); United States v. Yost,

479 F.3d 815, 819 (11th Cir. 2007) (per curiam).

       6
          Though the government argues that we should review Singer’s claim under the more
stringent “plain error” standard, see United States v. Batson, 818 F.3d 651, 664 (11th Cir. 2016);
United States v. Straub, 508 F.3d 1003, 1010-11 (11th Cir. 2007), we need not decide whether
“plain error” review is appropriate because the standard we apply makes no difference ultimately
to the outcome of Singer’s appeal. For that reason, we apply the stricter de novo standard.
                                               18
                Case: 18-14294    Date Filed: 06/26/2020    Page: 19 of 46

         Singer contends the district court erred in denying his motion for judgment of

acquittal because, in his view, a reasonable jury could not find that the evidence was

sufficient to show either prong of the offense—that he intended to violate U.S. law

or that he took a substantial step towards committing the offense. We address each

argument in turn.

                                      a.     Intent

         Singer argues that the evidence at trial failed to show that he knew the

NanoStations required a license for exportation to Cuba. In Singer’s view, the

government was required to prove he was aware of the specific characteristic of the

NanoStations—their ability to encrypt communications—that resulted in their being

classified as controlled under the export regulations. Since he claims the evidence

did not demonstrate this, he asserts he is entitled to an acquittal on the smuggling

count.

         We begin, as always, with the statutory text. See Staples v. United States, 511
U.S. 600, 605 (1994). As we’ve noted, 18 U.S.C. § 554(a), the statute under which

Singer was convicted, makes it unlawful to “knowingly export[] . . . or attempt[] to

export . . . any merchandise, article, or object contrary to any law or regulation of

the United States.” Singer’s indictment charged that Singer attempted to export

items (the NanoStations) contrary to 50 U.S.C. § 1705 and 15 C.F.R. § 746.2(a).

Section 1705 of the IEEPA, in turn, provides that anyone who “willfully” attempts

                                            19
             Case: 18-14294     Date Filed: 06/26/2020    Page: 20 of 46

to violate any license, order, regulation, or prohibition issued under the IEEPA,

“shall, upon conviction,” be guilty of a felony.

      Because the law Singer was convicted under § 554(a) of violating was § 1705,

the statutory language at issue here actually includes two scienter requirements: §

554(a) employs the scienter standard “knowingly,” while § 1705 uses the term

“willfully.” Beyond that, though, the language in a vacuum is not especially helpful

to resolving whether the government must prove only that the defendant knew he

was engaged, and the defendant willfully engaged, in the act of exporting or

attempting to export, which happened to violate a law or regulation of the United

States, or whether instead the government must also prove that the defendant knew

that the particular export or attempted export at issue violated a law or regulation of

the United States.

      This case appears to raise an issue of first impression. But we are not without

guidance. The Supreme Court has written much on the scienter requirement of

various criminal statutes. We find these cases instructive here.

      In construing a statute’s scienter requirement where the statutory language is

not necessarily explicit on the precise question at issue, we keep in mind that a

statute’s scienter requirement nonetheless raises a question of congressional intent.

Rehaif v. United States, 139 S. Ct. 2191, 2195 (2019).             When we ascertain

congressional intent as it concerns scienter, “we start from a longstanding

                                          20
             Case: 18-14294      Date Filed: 06/26/2020   Page: 21 of 46

presumption, traceable to the common law, that Congress intends to require a

defendant to possess a culpable mental state regarding each of the statutory elements

that criminalize otherwise innocent conduct.” Id. (citation and internal quotation

marks omitted). To demonstrate how this presumption applies here, we review a

few cases that have construed the scienter requirement of different statutes

criminalizing the failure to comply with regulatory schemes.

      In Liparota v. United States, 471 U.S. 419 (1985), the defendant was

convicted of “knowingly us[ing] transfer[ring], acquir[ing], alter[ing], or

possess[ing] [Food Stamps] in any manner not authorized by [the statute] or the

regulations.” Id. at 420. The Supreme Court considered whether, in addition to

showing that the defendant knew that he had used, transferred, acquired, altered or

possessed Food Stamps, the government also was required to prove that the

defendant knew that he was acting in a way that the applicable statute or regulations

did not authorize. Id. at 421.

      The Court concluded it was. Id. at 425. As relevant here, the Supreme Court

reasoned that if that were not the case, the statute there would “criminalize a broad

range of apparently innocent conduct.” Id. at 426. For example, the applicable

statute required Food Stamps to be used to buy food at approved stores “at prices

prevailing in such stores.” Id. So if knowledge that the Food Stamps were being

used in a way inconsistent with the governing statute and regulatory scheme were

                                          21
             Case: 18-14294     Date Filed: 06/26/2020    Page: 22 of 46

not necessary, a Food Stamp recipient who used stamps to buy food from a store

that, without the recipient’s knowledge, charged higher prices to Food Stamp

participants would be guilty of criminal conduct. Id. The Court determined that

Congress could not have intended that broad interpretation. Id. at 427. So under

Liparota, the government had to prove both that the defendant used Food Stamps

and that he knew the facts that rendered his specific use unauthorized. Id. at 425;

see Elonis v. United States, 135 S. Ct. 2001, 2010 (2015).

      Similarly, Ratzlaf v. United States, 510 U.S. 135 (1994), involved a statute

that criminalized “willfully violating” a law that made it illegal to break a single

financial transaction that satisfied a financial institution’s reporting threshold into

smaller transactions so that the financial institution processing it would not have to

report the transaction. See id. at 136-37. There, the Supreme Court concluded that

the government must prove not only that the defendant knew of the financial

institution’s duty to report cash transactions over the threshold amount but also that

he knew that he had a duty not to cause the bank to fail to comply with its reporting

requirement by structuring his transaction into smaller transactions under the

threshold. Id. at 146-47. In support of this conclusion, the Court explained that

structuring financial transactions for some purposes can be legal, so structuring is

not “so obviously ‘evil’ or inherently ‘bad’ that the ‘willfulness’ requirement is

                                          22
               Case: 18-14294   Date Filed: 06/26/2020   Page: 23 of 46

satisfied,” regardless of whether the defendant knew that structuring in a given case

was illegal. Id. at 146.

      And in response to the dissent’s concerns that proving the defendant’s

knowledge of the fact that he had a duty to refrain from structuring would be

“impossible,” the Supreme Court explained that “[a] jury may, of course, find the

requisite knowledge on defendant’s part by drawing reasonable inferences from the

evidence of defendant’s conduct.” Id. at 149 n.19. By way of example, the Supreme

Court cited a Second Circuit decision where the circuit court held that evidence that

the government had taken “affirmative steps” to make the defendant aware of a

reporting duty through the use of visual notices and verbal announcements over the

public address system “support[ed] [the] inference that [the] defendant ‘willfully

violated’” a statute. Id. (citing United States v. Dichne, 612 F.2d 632, 636−38 (2d

Cir. 1979)).

      Our predecessor Court faced a similar problem in United States v. Warren,

612 F.2d 887 (5th Cir. 1980) (en banc), before the Supreme Court decided Liparota

and Ratzlaf. There, the statute at issue made it unlawful to knowingly and willfully

transport more than $5,000 beyond a United States border without filing the required

report. Id. at 890−91. Our predecessor Court concluded that to convict a defendant

under this statute, the government must prove not only that the defendant knew she

was transporting more than $5,000 into the United States but also that she knew she

                                         23
             Case: 18-14294     Date Filed: 06/26/2020   Page: 24 of 46

was required to report that fact and nonetheless did not. Id. at 890. Similar to what

the Supreme Court would later note in Ratzlaf, we then explained that to prove the

second part of this equation, the government could show either that the defendant

had been warned of the reporting requirement or that the defendant otherwise knew

of the reporting requirement before being arrested for the crime. Id.

      From these cases, we glean two significant principles.

      First, when it comes to statutes that criminalize violations that regulate what

can otherwise be innocent conduct, it is not enough that the defendant engaged in

actions that the law prohibits. Rather, we must construe the statute to satisfy the

“longstanding presumption, traceable to the common law, that Congress intends to

require a defendant to possess a culpable mental state regarding each of the statutory

elements that criminalize otherwise innocent conduct.” Rehaif, 139 S. Ct. at 2195

(citation and internal quotation marks omitted).

      And second, to prove that the defendant had the necessary factual knowledge,

the government need not directly demonstrate that the defendant knew the facts that

made his conduct a violation of the law.             Rather, the government may

circumstantially prove the defendant’s knowledge through evidence that allows the

jury to draw that reasonable inference. Among other methods of establishing this

element, the government may present evidence that it engaged in “affirmative

efforts” to warn the defendant of the regulatory requirement he later violated or that

                                         24
             Case: 18-14294     Date Filed: 06/26/2020    Page: 25 of 46

the defendant’s conduct indicated that he knew of the fact that a regulation or statute

prohibited his conduct at the time he engaged in it.

      We apply these rules here when we consider whether the government

presented sufficient evidence to establish intent.       First, we hold that, as the

government charged Singer, it was required to prove both that Singer violated 50

U.S.C. § 1705 and 15 C.F.R. § 746.2(a) and that Singer knew of the facts that made

his conduct a violation of these provisions. We reach this conclusion because, as

with the use of Food Stamps in Liparota, the structuring of financial transactions in

Ratzlaf, and the transportation of money into the United States in Warren, the

exportation of goods from the United States is not “so obviously ‘evil’ or inherently

‘bad’ that the ‘willfulness’ requirement is satisfied,” Ratzlaf, 510 U.S. at 146, even

if Singer did not know of the facts that rendered his conduct illegal. And when it

comes to crimes involving complex regulatory schemes, we generally do not

criminally punish individuals engaged in conduct they reasonably believed to be

innocent.

      Second, we conclude that the evidence the government presented at trial

satisfied this knowledge standard. In particular, the government put on evidence that

it had repeatedly warned Singer of his “RESPONSIBILITY TO COMPLY WITH

ALL OFAC & COMMERCE’S REGULATIONS.” See ECF No. 56-1 at 15, 20, 25,

32, 44, 51, 100. And the several CG-3300 forms Singer signed and submitted to

                                          25
              Case: 18-14294    Date Filed: 06/26/2020   Page: 26 of 46

obtain a permit to enter Cuban Territorial Seas each expressly warned Singer that

(1) his application “must include a Department of Commerce export license for any

vessel or conveyance entering Cuban seas”: (2) “[f]ailure to obtain all of the

appropriate permits and licenses prior to travel to Cuba may result in felony

prosecution”; and (3) “[d]etailed information on the U.S. embargo [of Cuba] can be

obtained from [OFAC] in Miami at 305 810-8140 & the Department of Commerce

(DOC) at 954 366-7540 or 202 482-4811.” Id. at 17, 22, 27, 34, 42, 46, 53, 104,

106, 115, 117 (emphasis added). Plus, Singer himself sent letters in support of his

CG-3300 applications that expressly stated what the “support for the Cuban People”

general license covers and that noted, “For a complete description of what this

general license authorizes and the restrictions that apply, see 31 CFR § 515.574.”
Id. at 19, 24, 38, 55.

       Besides the evidence of warnings the government gave to Singer, Singer’s

conduct suggested he knew he was exporting items to Cuba that required a license

that he did not have. For example, on his CG-3300 applications, Singer described

the purpose of his scheduled May 2, 2017, visit to Cuba as “SUPPORT OF THE

CUBAN PEOPLE, FOR A MOTORCYCLE RALLY.” ECF No. 56-1 at 17. True,

the presence on May 1 of several motorcycles and other individuals on La Mala

supports the notion that Singer did intend to attend a motorcycle rally in Cuba. And

Singer testified at trial that he believed the “support for the Cuban People” general

                                         26
                Case: 18-14294        Date Filed: 06/26/2020       Page: 27 of 46

license allowed the exportation of certain items that Cubans could use in their homes

to communicate, including cell phones, computers, and modems.

       But the jury was free to disbelieve Singer, particularly in light of Singer’s

repeated recitations in his CG-3300 application paperwork of what the “support for

the Cuban People” general license authorizes, a recitation that does not include the

exportation of items on the Compliance Control List, such as the NanoStations. See

United States v. Brown, 53 F.3d 312, 314 (11th Cir. 1995) (“[W]hen a defendant

chooses to testify, he runs the risk that if disbelieved ‘the jury might conclude the

opposite of his testimony is true.’”) (citation omitted).

       That Singer lied to officers and said he had nothing to declare but the few

items in plain view (which did not include the NanoStations) also supports the

conclusion that Singer knew he was not allowed to export the NanoStations without

a license. Otherwise, there would have been no reason for him to have lied about

the NanoStations and hidden them in a compartment under a bed that was screwed

to the floor. In addition, when the officers found the NanoStations in the hidden

compartment, Singer admitted he lied about them and about the reason the bed was

screwed to the floor because he did not want Blyth, Hatfield, and the other United

States officers to find them. 7

       7
        Astute readers might recall that Singer testified he told the officers that he lied about the
NanoStations because he did not want Cuban authorities—not United States authorities—to find

                                                 27
                Case: 18-14294       Date Filed: 06/26/2020        Page: 28 of 46

       And when Korb interviewed Singer upon his return from Cuba on May 5,

2017, Singer said the NanoStations were for the men who were initially supposed to

travel with him. But agents seized 303 NanoStations, and only eight passengers

were scheduled to travel with Singer to Cuba. Plus, none of those eight were Cubans.

Rather, they were all from the United States or South Africa. See ECF No. 56-1 at

17-18. Singer’s implausible response to Korb’s inquiry further supports a finding

that Singer knew the NanoStations could not be exported to Cuba without a license.

His lie indicates that he was trying to hide the fact that he knew he needed an export

license for the NanoStations by trying to falsely suggest that he believed the

NanoStations somehow fell into the “support for the Cuban People” general license

or exception.

       We conclude that this evidence certainly allowed the jury to draw the

reasonable inference that Singer knew that he required a license to be able to export

the NanoStations to Cuba.

       Singer takes issue with this conclusion. He argues that we cannot infer

anything from the facts that the NanoStations were hidden in the compartment under

the bed and that Singer lied about them, since other items that did not require a

them. For their part, though, the officers testified that Singer said he lied about the NanoStations
because he did not want United States authorities to know about them. As we have explained, on
appeal of a conviction, we view the evidence in the light most favorable to the government.
Grzybowicz, 747 F.3d at 1304.
                                                28
             Case: 18-14294     Date Filed: 06/26/2020   Page: 29 of 46

license were found in the same compartment with the NanoStations, and Singer lied

about them as well. According to Singer, he had no reason to lie about the other

items because they did not require a special license to export to Cuba.

      But we can think of one. Singer may well have placed the other items in the

hidden compartment because that was the most convenient place to stow them,

because a full compartment made it less likely that the NanoStations would move

around en route, or because he lacked space elsewhere. Whatever the reason, one

thing is clear: had Singer declared the other items that were in the hidden

compartment under the bed, Singer knew that the officers, who were conducting an

outbound inspection, would have required Singer to show the items to them. Then

Singer would have had to unscrew the bed and reveal the hidden compartment.

When he did so, the officers necessarily also would have found the NanoStations.

So we are not persuaded that the jury was required to view Singer’s lies to the

officers and his hiding of the NanoStations as conduct consistent with a lack of

knowledge that he was required to obtain a license before exporting the

NanoStations to Cuba.

                                b. Substantial Step

      Next, we consider whether sufficient evidence established that Singer took a

“substantial step” towards the commission of the offense.

      A substantial step is an “objective act[] that mark[s the defendant’s] conduct

                                         29
             Case: 18-14294     Date Filed: 06/26/2020    Page: 30 of 46

as criminal such that his acts as a whole strongly corroborate the required

culpability.” United States v. Stahlman, 934 F.3d 1199, 1225 (11th Cir.) (citation

and internal quotation marks omitted), cert. denied., 140 S. Ct. 530 (2019). Mere

planning or preparation to engage in a crime is not enough to constitute a “substantial

step.” St. Hubert, 909 F.3d at 351 (citation omitted). Rather, to take a substantial

step, the defendant must engage in “objectively culpable and unequivocal acts

toward accomplishing the crime.” Id. (citation omitted). Here, the jury instructions

defined “substantial step” as “an important action leading up to the committing of

an offense—not just an inconsequential act. It must be more than simply preparing.

It must be an act that would normally result in committing the offense.” ECF No.

47 at 14.

      Singer argues that he did not undertake a “substantial step” towards

committing attempted exportation because he canceled his trip to Cuba on May 2,

2017. According to Singer, he did nothing more than make mere preparations to

travel, and he canceled his trip after the officers visited him on May 1.

      Singer claims Blyth’s testimony corroborates his claim. He also notes that the

eight other individuals who were scheduled to travel with him to Cuba left with their

belongings on May 1. In addition, Singer points to the fact that his boat was moored

in the same location on May 2 as it was on May 1. And on May 2 when the officers

arrived at the marina, La Mala’s engines were not running and, according to Singer,

                                          30
               Case: 18-14294        Date Filed: 06/26/2020       Page: 31 of 46

no other preparations for departure had been made. Because Singer did not begin

his voyage on May 2, and because it is not a crime to merely possess the

NanoStations, Singer asserts that no evidence supports a finding that he took a

substantial step towards the commission of the charged offense. We disagree.

      First, we disagree with Singer’s characterization of Blyth’s testimony—that

Blyth agreed that Singer altogether canceled the May 2 trip to Cuba. 8 True, Blyth

      8
          The relevant exchange between defense counsel and Blyth was as follows:

              Q:   How many people were there [on May l , 2017]?
              A:   Approximately eight.
              Q:   And how many motorcycles were there as well?
              A:   It's hard to say. I know I observed a number of motorcycles on the boat.

                                             ***
              Q: You didn’t inspect the boat that day, correct?
              A: Correct.
              Q: So you don’t know what was on the boat that day, correct?
              A: Correct.
               Q: And you told Mr. Singer, I will be back, correct?
               A: I told Mr. Singer he couldn’t leave because his permit wasn’t
              for May 1. I told him he could leave on May 2, and that, yes, we
              would be back to inspect his vessel.
                                              ***
              Q: And when you came back the second day [May 2, 2017], all those seven or
              eight individuals, they weren’t there anymore, right?
              A: Correct.
              Q: Those Harleys or motorcycles are gone, correct?
              A: Correct.
              Q: Trip was canceled, correct?
              A: Yes.
              Q: He told you—Mr. Singer told you he canceled the trip, correct?
              Prosecutor: Objection
              Court: Sustained.
              A: Mr. Singer didn’t cancel the trip.
              Prosecutor: The objection is sustained.
              Witness: I am sorry.

                                               31
              Case: 18-14294    Date Filed: 06/26/2020     Page: 32 of 46

did agree that, as of May 2 (when he returned to Singer’s boat), the “trip was

canceled.” But it appears this statement meant something other than what Singer

suggests.

      The words themselves did not necessarily mean that Singer had decided not

to travel to Cuba. Blyth could have meant that the original plan to take the eight

other individuals to Cuba had been canceled, but Singer still planned to make the

trip to deliver the electronics. Indeed, when pressed with the specific question of

whether Singer told him he canceled the trip, Blyth said, “Singer didn’t cancel the

trip.” And while during his own testimony, Singer indicated that he canceled the

trip, the jury was free to discredit this testimony. See Brown, 53 F.3d at 314; United

States v. Jiminez, 564 F.3d 1280, 1285 (11th Cir. 2009).

      Second, the evidence supports the reasonable conclusion that Singer did not

cancel his trip altogether (the same evidence indicates that Blyth understood this to

be the case). Singer filed for and obtained a valid CG-3300 permit that would have

allowed him to sail to Cuba on May 2 (the date the items were seized). And when

law enforcement returned to the dock on May 2 to conduct an outbound inspection

of the boat, Singer reportedly told Blyth that he had a “valid [Form] 3300 that would

allow him to sail to Cuba, and that he wished to sail to Cuba.” ECF No. 58 at 12-

ECF No. 58 at 47-48.
                                         32
              Case: 18-14294     Date Filed: 06/26/2020    Page: 33 of 46

13. Plus, had Singer canceled his voyage on May 1, he would have had no reason

to make a declaration of what was onboard when asked during the outbound

inspection. Indeed, there would have been no reason for Blyth to have conducted an

outbound inspection of Singer’s boat if Singer had canceled his trip to Cuba. After

all, an outbound inspection is conducted so that a vessel may depart the United

States.

      Finally, Singer actually did travel to Cuba by boat on May 3—the day after

law enforcement seized the NanoStations. Singer took the remaining cargo during

this trip. While Singer testified that he canceled the original trip and took the trip a

day later only after others at the marina convinced him to make the voyage, the jury

was free to disbelieve him, particularly in light of the circumstantial evidence that

contradicted Singer’s assertion. And even though Singer testified he decided on

May 1 to cancel the trip, he did not remove all the cargo from his ship, including the

four or five items in plain view and the NanoStations (and other items) from under

his bed.

      For these reasons, when we view the evidence in the light most favorable to

the government, we conclude that a reasonable jury had sufficient evidence to find

that Singer took a substantial step towards exporting the NanoStations to Cuba.

B.   The district court did not err in declining to give Singer’s proposed jury
     instruction

                                          33
             Case: 18-14294     Date Filed: 06/26/2020   Page: 34 of 46

     Singer next contends the district court erred when it failed to give his proposed

jury instruction on ignorance of the law. This argument relates to the intent issue

we discussed above in Section III.A.2.a. Singer asserts that, because the government

was required to show he knew the NanoStations could not be exported to Cuba

without a license, the district court should have instructed the jury that Singer’s

ignorance of the relevant regulation was a defense.

     Singer proposed the following jury instruction:

             The defendant has asserted that he was not aware of the
             export control laws that prohibited the attempted export of
             the Ubiquiti Nanostations M2 Network Modems. As a
             general rule, ignorance of the law is no excuse. However,
             in this case ignorance of the law is a defense to crimes
             charged against the defendant.

ECF No. 38 at 2. The district court declined to give the requested instruction and

instead instructed the jury as follows:

                   Title 18, United States Code, Section 554, makes it
             a crime for anyone to knowingly or fraudulently attempt
             to export or send any merchandise from the United States
             contrary to any law or regulation of the United States.

                   For you to find the Defendant guilty of this crime,
             you must be convinced that the Government has proved
             each of the following beyond a reasonable doubt:

                    First:     That the Defendant knowingly or
             fraudulently attempted to export or send merchandise, as
             described in the second superseding indictment, or that the
             Defendant concealed or facilitated the concealment of
             such merchandise, prior to exportation, knowing the same
             to be intended for exportation;
                                          34
             Case: 18-14294     Date Filed: 06/26/2020   Page: 35 of 46

                   Second:      That the Defendant’s attempted
             exportation or sending was contrary to Title 50, United
             States Code, Section 1705 of Section 746.2(a) of the
             Export Administration Regulations; and

                   Third:     That the Defendant knew that
             exportation or sending of the merchandise was
             contrary to law or regulation.

                   “Merchandise” means goods, wares, and chattels of
             every description, and includes merchandise the
             exportation of which is prohibited.

                    To “export” means to send or carry from the United
             States to another country.

                    “Fraudulently” means with the specific intent to
             deceive or cheat, for the purpose of either causing some
             financial loss to another, or bringing about some financial
             gain to one’s self.
ECF No. 47 at 11-12 (emphasis added).

      We have recognized that a criminal defendant has a right to a jury instruction

on his proposed theory of defense, provided that theory of defense is a valid one and

some evidence at trial supports the instruction. See United States v. Arias, 431 F.3d
1327, 1340 (11th Cir. 2005). We review a district court’s refusal to give a requested

jury instruction for abuse of discretion. United States v. Jeri, 869 F.3d 1247, 1268

(11th Cir. 2017); United States v. Dohan, 508 F.3d 989, 993 (11th Cir. 2007) (per

curiam); United States v. Eckhardt, 466 F.3d 938, 947 (11th Cir. 2006). We will

reverse a district court's refusal to give a requested jury instruction only if the

                                         35
               Case: 18-14294    Date Filed: 06/26/2020    Page: 36 of 46

proposed instruction correctly reflects the law, the jury instructions the district court

actually gave did not address the proposed instruction, and the district court’s refusal

to give the requested instruction “seriously impaired the defendant’s ability to

present an effective defense.” United States v. Horner, 853 F.3d 1201, 1208 (11th

Cir. 2017) (quoting United States v. Drury, 396 F.3d 1303, 1318 (11th Cir. 2005)

(internal quotation marks omitted)). So long as the district court’s jury instructions

“accurately reflect[] the law, the trial judge has wide discretion to decide on the style

and wording of the instruction.” Id. We “examine[] the jury charge[] as a whole,

determining whether the entire charge sufficiently instructed the jury about the

issues.” Id.

      Here, we conclude the district court did not abuse its discretion when it

declined to give Singer’s proposed instruction. The court was not required to adopt

the precise wording of Singer’s proposed charge, since it nonetheless covered the

substance of Singer’s proposed instruction in the charge it gave. Specifically, the

district court’s instruction informed the jury that to convict Singer on the attempt

count, the jury was required to find that Singer knew he was attempting to export

NanoStations to Cuba, that he knew he was doing so without a license, and that he

knew those actions violated federal law or regulations.

      That is all that was necessary to instruct the jury on the scienter requirement

here. Under this instruction, a reasonable jury could not have convicted Singer had

                                           36
              Case: 18-14294    Date Filed: 06/26/2020    Page: 37 of 46

the government failed to present sufficient evidence establishing that Singer knew

of the fact that the law and regulations prohibited the exportation of the NanoStations

to Cuba without a valid license authorizing that conduct.

      Plus, Singer’s proposed instruction risked confusing the jury. As we have

explained, the government was required to show that Singer knew of the fact that

the law and regulations prohibited the exportation to Cuba of the NanoStations

without a valid license. Singer’s proposed instruction unnecessarily introduced the

concept of “ignorance of the law.” Even the Supreme Court has not always

consistently differentiated between the concepts of knowledge of the facts and

knowledge of the law when it comes to the scienter necessary to establish a criminal

violation of a regulatory scheme. Compare Elonis, 135 S. Ct. at 2010 (describing

Liparota as having construed the statute at issue there as “requir[ing] knowledge of

the facts that made the use of the food stamps unauthorized”) with Bryan v. United

States, 524 U.S. 184, 193 n.15 (1998) (describing Liparota as having “concluded

that both the term ‘knowing’ . . . and the term ‘knowingly’ . . . literally referred to

knowledge of the law as well as knowledge of the relevant facts”). We see no reason

to complicate the jury’s task by unnecessarily employing complicated concepts in

the instructions.

      The refusal to give Singer’s proposed instruction also did not impair Singer’s

ability to present his defense, let alone substantially impair it. Singer was just as

                                          37
                Case: 18-14294           Date Filed: 06/26/2020   Page: 38 of 46

able to argue to the jury that the government failed to prove he knew of the fact that

federal law prohibited him from exporting the NanoStations to Cuba. See Jeri, 869
F.3d at 1268. As we have noted, Singer even testified in an attempt to convince the

jury that he was not aware of the fact that federal law prohibited him from exporting

the NanoStations to Cuba. Singer also presented expert testimony to establish that

the regulations at issue were complex and hard to understand. And he tried to

convince the jury that he believed the “support for the Cuban People” general license

exempted him from the need to obtain a license to export the NanoStations.

      In short, the district court’s jury instructions adequately covered Singer’s

proposed instruction, and the district court did not abuse its discretion when it

declined to give Singer’s proposed jury instruction on ignorance of the law.

C.    The district court did not err in applying the sentencing enhancement for
      obstruction of justice

      Finally, Singer challenges the district court’s application of a two-level

sentence enhancement for obstruction of justice. The district court determined that

the enhancement applied because it found that Singer committed perjury during trial.

In particular, the district court concluded Singer perjured himself when he testified

that he hid the items in the compartment under his bed from Cuban authorities, not

from United States authorities. 9 When it comes to the imposition of an enhancement

      9
          Singer testified as follows:

                                                  38
               Case: 18-14294       Date Filed: 06/26/2020        Page: 39 of 46

for obstruction of justice, we review the district court’s factual findings for clear

error and its application of those facts to the Sentencing Guidelines de novo. United

States v. Guevara, 894 F.3d 1301, 1311 (11th Cir. 2018).

                      Q: Okay. But then after they found [the compartment under
                         your bed with the 303 NanoStations], you told law
                         enforcement that you didn’t want them to find it?
                      A: I did not, sir.
                      Q: So Agent Hatfield – or Officer Hatfield was lying when
                         he said that?
                      A: I did not say that I was hiding it from the authorities.
                         And I believe, if I recollect, I listened very carefully to
                         Mr. Hatfield, he says I was hiding it from law
                         enforcement. He didn’t say whose [sic].
                      Q: So that’s your testimony, that he was – Hatfield was
                         ambiguous as to what you were saying?
                      A: I was hiding it from Cuban law enforcement, sir.
                      Q: Did you say that to him?
                      A: Yes, I did.
                      Q: You didn’t say you were hiding it from U.S. law
                         enforcement?
                      A: No, sir.
                      Q: Just hiding it from some law enforcement?
                      A: Cuban law enforcement.
                      Q: You didn’t say you were hiding it from Agent Blyth?
                      A: No, sir.
                      Q: Not from Officer Hatfield?
                      A: I didn’t want to help him, sir.
                                                    ***
                      Q: You are saying that the testimony of Agent Blyth and
                         Agent Hatfield about your lie is incorrect?
                      A: You have to be more specific.
                      Q: When they said you lied about hiding it from them, they
                         were lying, is that your testimony?
                      A: I would have to assume that they said I was hiding it from
                         them. I was hiding it from the Cuban authorities.
ECF No. 74 at 113-114. Singer’s testimony reflects that he steadfastly contended to Blyth and
Hatfield that he lied about hiding the NanoStations under the bed because he was hiding them from
Cuban authorities.
                                               39
             Case: 18-14294     Date Filed: 06/26/2020    Page: 40 of 46

      Here, we find no error. Section 3C1.1 of the Sentencing Guidelines governs

the application of an enhancement for obstruction. It provides that the defendant’s

offense level will be increased by two levels if

             (l) the defendant willfully obstructed or impeded, or
             attempted to obstruct or impede, the administration of
             justice with respect to the investigation, prosecution, or
             sentencing of the instant offense of conviction, and (2) the
             obstructive conduct related to (A) the defendant’s offense
             of conviction and any relevant conduct; or (B) a closely
             related offense.

See U.S.S.G. § 3C1.1. A court may apply the obstruction enhancement where the

defendant testifies on his own behalf and perjures himself while doing so. See

U.S.S.G. § 3C1.1 cmt. n.2 (explaining that the enhancement is not intended to

punish a defendant who exercises his constitutional right to testify, “other than a

denial of guilt under oath that constitutes perjury”); see also United States v.

Dunnigan, 507 U.S. 87, 96-97 (1993), abrogated on other grounds by United States

v. Wells, 519 U.S. 482 (1997). Indeed, the commentary to § 3C1.1 provides

examples of conduct considered to be “obstructive” under Section 3C1.1, including

committing perjury, U.S.S.G. § 3C1.1 cmt. n.4(B), and “providing materially false

information to a judge or magistrate judge,” U.S.S.G. § 3C1.1, cmt. n. 4(F).

      Perjury is the “false testimony concerning a material matter with the willful

intent to provide false testimony.” United States v. Duperval, 777 F.3d 1324, 1337

(11th Cir. 2015) (citation and internal quotation marks omitted). Note 6 to Section

                                         40
             Case: 18-14294     Date Filed: 06/26/2020   Page: 41 of 46

§ 3C1.1 defines materially false information as “information that, if believed, would

tend to influence or affect the issue under determination.” See U.S.S.G. § 3C1. l

cmt. n.6. Usually, material testimony goes to the issue of a defendant’s guilt. See

United States v. McKinley, 732 F.3d 1291, 1298 (11th Cir. 2013).

      It makes sense then, that the application of the enhancement requires that a

district court “make an independent factual finding that the defendant gave perjured

testimony on a material matter.” United States v. Vallejo, 297 F.3d 1154, 1168 (11th

Cir. 2002); see also Dunningan, 507 U.S. at 95. Although a district court should

preferably “make specific findings by identifying the materially false statements

individually, it is sufficient if the court makes a general finding of obstruction

encompassing all the factual predicates of perjury.” Duperval, 777 F.3d at 1337

(citation and internal quotation marks omitted); see also Guevara, 894 F.3d at 1311

(noting that sentencing courts should make specific findings of fact when they adjust

sentences for obstruction of justice, but recognizing if the record supports the

adjustment by clearly reflecting the basis for it, the court need not make

individualized findings regarding obstruction of justice).

       Singer challenges the district court’s application of the enhancement on two

grounds. First, he contends the district court failed to make specific, independent

findings of perjury and instead merely found the jury’s verdict to be a “definitive

referendum” on the falsity of Singer’s testimony as to why he concealed the

                                         41
              Case: 18-14294      Date Filed: 06/26/2020     Page: 42 of 46

NanoStations on his boat. Second, Singer asserts, even assuming the statements he

made during trial were false, they were not material because he admitted that he lied

to agents and apologized for that conduct. We address each ground, in turn.

       1. The district court made the necessary findings to support its conclusion
          that Singer’s testimony was false

       The district court made the required findings regarding perjury. It identified

specific testimony it found to be false—Singer’s statements that he did not intend to

conceal cargo from U.S. law enforcement and that he canceled his trip to Cuba—

and concluded Singer knew them to be false when he uttered them on the stand. ECF

No. 97 at 5-6. In doing so, the district court did not merely adopt the jury’s verdict

to determine that Singer’s testimony was false.              Rather, the district court

independently evaluated the issue and provided a sufficient explanation for its

conclusion. Indeed, the district court expressed its own view that Singer “testified

falsely” and stated that it was “satisfied that [Singer’s] testimony was ‘knowingly

false.’” ECF No. 97 at 5-6. When the government requested the enhancement for

obstruction of justice, the district court stated, “I believe that is appropriate. [Singer]

went to trial and he testified. He testified falsely.” ECF No. 97 at 5.

      In deciding to apply the enhancement, the district court judge emphasized,

             I was the judge at the trial and I recall this testimony and I
             thought it was material to the case and to his defense. He
             took the stand and he tried to marginalize his criminal
             conduct by suggesting that he wasn’t trying to conceal it

                                            42
             Case: 18-14294     Date Filed: 06/26/2020   Page: 43 of 46

             from U.S. Government officials but from Cuban officials,
             as if for that reason it was therefore okay.

             That went right to his credibility and, obviously, the jury
             chose not to believe him, and that was one of the core
             defenses that he had. So I can’t conclude that it was not
             material.
Id. at 8-9. This explanation is sufficient because it expressed the district court’s

independent view that Singer committed perjury. The district judge relied on his

recollection of the evidence and the credibility of the witnesses. We do not second-

guess the district court’s credibility determination. See United States v. Williams,

340 F.3d 1231, 1240 (11th Cir. 2003) (“An appellate court is not in a position to

assess a defendant’s demeanor, apparent sincerity, intonation, expression,

gesticulations, and a wide range of other considerations that are pertinent in

determining whether he has perjured himself.”).

      The evidence also supports the district court’s conclusion that Singer testified

falsely with respect to both statements. First, and as we have already discussed, the

evidence supports a finding that Singer testified falsely when he said that on May 1,

2017, he canceled his trip to Cuba.

      Second, the evidence supports a finding that Singer testified falsely when he

said he hid the NanoStations under his bed from Cuban authorities, not United States

authorities. Singer failed to declare the items under the bed when United States law

enforcement boarded his boat and conducted an inspection on May 2. If Singer were

                                         43
             Case: 18-14294     Date Filed: 06/26/2020    Page: 44 of 46

merely hiding the items from Cuban law enforcement, there would have been no

reason not to advise United States authorities about the cargo—particularly if Singer

did not realize that he could not export the NanoStations to Cuba without a license.

Singer’s failure to tell United States law enforcement about the items raised a

reasonable inference that he was trying to hide the items from United States officials

and that he was lying during his testimony. Finally, Blyth and Hatfield both testified

that Singer admitted on May 2 that he was hiding the NanoStations from United

States law enforcement. Their testimony directly contradicted Singer’s. And the

district court was free to accept their testimony over Singer’s.

      2. The district court did not err in concluding that Singer’s false statements
         were material

      The district court also concluded that the false testimony at issue “was

material to the case and to [Singer’s] defense.” ECF No. 97 at 8. In particular, the

district court found the misstatement about hiding the cargo from Cuban authorities

(as opposed to United States authorities) to be material because it was “one of the

core defenses that [Singer] had.” ECF No. 97 at 9. We agree.

      As we have discussed, to convict Singer of violating § 554(a), the government

had to prove that Singer knew that the attempted exportation to Cuba was “contrary

to [a] law or regulation of the United States.” See 18 U.S.C. § 554(a). So Singer’s

decision to hide the cargo from United States authorities (as opposed to Cuban

authorities) provided strong circumstantial evidence that Singer knew the attempted
                                          44
             Case: 18-14294     Date Filed: 06/26/2020   Page: 45 of 46

exportation violated United States law.       The district court could have fairly

concluded that when Singer falsely testified that he hid the cargo from Cuban

authorities, he attempted to mislead the jury into believing that he was unaware of

the criminal nature of his conduct. If Singer had testified truthfully—that he hid the

cargo from United States authorities—it would have supported the inference that he

knew the attempted transportation of the goods violated the law. For these reasons,

the misstatement was material to the case.

      Singer attempts to persuade us that his apology to law enforcement for lying

negates the materiality element. We disagree. Although Singer did apologize for

failing to declare the cargo under his bed after United States officers found it, he

claimed that he lied about concealing it because he was angry with Blyth. But

significantly, Singer never conceded that he lied to United States law enforcement

when he claimed he hid the NanoStations from Cuban authorities. That he hid the

cargo at all and from whom specifically he sought to hide it concern two different

issues. So Singer’s apology concerning one has no bearing on the other.

      Because the record amply supports the district court’s conclusion that Singer

perjured himself when he testified that he told United States law enforcement that

he had hidden the NanoStations from Cuban officials, not from United States ones,

we need not consider the other misstatement by Singer—that he canceled his trip to

                                         45
             Case: 18-14294     Date Filed: 06/26/2020    Page: 46 of 46

Cuba. Ultimately, the district court did not clearly err when it imposed the two-level

enhancement for obstruction.

                                         IV.

      For the foregoing reasons, we conclude that sufficient evidence supported the

verdict here, the district court did not err in declining Singer’s proposed ignorance-

of-the-law jury instruction, and it similarly did not err in sentencing Singer. We

therefore affirm Singer’s conviction and sentence.

      AFFIRMED.

                                         46