Defendant's Reply to Response to Motion by Eric Dean Sheppard — USA v. Sheppard (Dkt. 249, S.D. Fla.)

Record facts

U.S. District Court for the Southern District of Florida · No. 1:22-cr-20290-BB · Doc. 249 · 2024-05-31 · Docket on CourtListener

Full text

1 
UNITED STATES DISTRICT COURT 
SOUTHERN DISTRICT OF FLORIDA 
 
CASE No. 22-20290-CR-BLOOM 
 
UNITED STATES OF AMERICA, 
 
 
vs. 
 
 
 
 
 
 
 
ERIC DEAN SHEPPARD, 
 
 
 
 
 
 
 
 
 
 
 
Defendant. 
_______________________________/ 
 
 
SHEPPARD’S REPLY IN SUPPORT OF  
[DE 240] PROVISIONAL MOTION FOR RELEASE PENDING APPEAL,  
OR IN THE ALTERNATIVE, FOR SELF-SURRENDER 
 
 
Defendant Eric Dean Sheppard has been released on bond for two years during 
the pendency of these proceedings without incident. Despite Sheppard’s 
demonstrated history of compliance with conditions of release, the government asks 
this Court to deny him bond pending appeal. See DE 245. It offers only two 
arguments, both of which lack merit. First, the government halfheartedly suggests 
that Sheppard is a flight risk because he faces a lengthy prison sentence, ignoring 
the many factors showing otherwise—not only his compliance to date, but also his 
deep roots in the jurisdiction. Second, the government contends that Sheppard’s 
appeal will not present substantial questions of law; briefing and argument on 
Sheppard’s pending post-trial motions show otherwise. 
At a minimum, the Court should allow Sheppard to self-surrender. The 
government offers no real argument in opposition to this modest request. 
 
 
Case 1:22-cr-20290-BB   Document 249   Entered on FLSD Docket 05/31/2024   Page 1 of 7

2 
ARGUMENT 
 
I. 
THE COURT SHOULD RELEASE SHEPPARD PENDING APPEAL 
Section 3143(b) requires this Court to release Sheppard on bond if it finds: (1) 
by clear and convincing evidence that he is not a flight risk or danger to the 
community; (2) that his appeal is not for purposes of delay; and (3) the appeal raises 
a substantial question that (4) would result in reversal or a more favorable sentence 
if Sheppard prevails. 18 U.S.C. § 3143(b). The government does not argue that 
Sheppard is a danger to the community. Nor does it separately contest elements 
(2) and (4). See DE 245 at 3, 7-8 (acknowledging that if Sheppard prevails on appeal 
“his sentence will result in zero jail time”). The government’s arguments that 
Sheppard is a flight risk and that his appeal will not raise substantial questions are 
meritless.  
A. 
Sheppard Is Not a Flight Risk 
The government acknowledges that its “main reason for opposing” bond is 
not its belief that Sheppard is a flight risk. DE 245 at 2. Indeed, the government stops 
short of arguing that Sheppard actually is a flight risk, observing only that Sheppard 
has an “incentive to flee” because he “is facing a lengthy prison sentence.” That 
observation does not justify imprisoning Sheppard during his appeal for several 
reasons.1 
 
1 Taken at face value, the government’s argument would seem to suggest that any 
defendant facing seven or more years in prison would be a flight risk and thus 
ineligible for bond. But if Congress wanted to deny bond pending appeal to 
defendants facing significant sentences, it would have said so. Instead, it enacted 
Section 3143(b), which allows the Court to focus on case specific factors, like 
Sheppard’s history of compliance with conditions of release and many ties to the 
jurisdiction. 
Case 1:22-cr-20290-BB   Document 249   Entered on FLSD Docket 05/31/2024   Page 2 of 7

3 
To start, Sheppard had the same basic “incentive to flee” the moment he was 
convicted of four counts of wire fraud and two counts of aggravated identity theft. 
But this Court allowed Sheppard to remain on bond (which requires a finding by 
clear and convincing evidence that he was not likely to flee, 18 U.S.C. § 3143(a)(1)). 
Since then, Sheppard has complied with all conditions of release, including after 
probation calculated a 57-71 month prison term and the government suggested even 
longer. There is nothing to suggest Sheppard would act any differently on appeal. 
His history of compliance with conditions of release while staring down a lengthy 
prison sentence is compelling evidence that he will comply with conditions of 
release while appealing a lengthy prison sentence (if one were imposed).  
The government also ignores Sheppard’s many ties to the jurisdiction. The 
government notes that Sheppard does not have children living at his home, DE 245 
at 2, but the government is mistaken. As the Probation Office has confirmed, 
Sheppard has a 15-year-old son who resides at home with Sheppard and his wife, 
PSR at para. 88, and attends high school in this community. He also has a college-
age daughter with a serious medical condition. Id. Moreover, his children are not the 
only anchors: Sheppard has other family members and numerous friends who 
submitted letters of support. See DE 247 (motion to seal), 248 (letters filed under 
seal). For his part, Sheppard is a cancer survivor with regular appointments with his 
doctors in South Florida, and he has substantial community and business interests in 
this jurisdiction.  
Finally, the government notes that Sheppard has “more financial resources 
than most defendants.” DE 245 at 2. The government’s suggestion appears to be that 
wealthy defendants are a greater flight risk than poor defendants. That is a dubious 
proposition, and the government cites nothing in support. (If a defendant were poor, 
the government would cynically argue that the defendant has little to lose by fleeing.) 
But the Court need not engage in class-based speculation to reject the government’s 
Case 1:22-cr-20290-BB   Document 249   Entered on FLSD Docket 05/31/2024   Page 3 of 7

4 
argument. Sheppard has committed substantial financial resources to continue 
litigating his case, retaining additional counsel versed in this area of the law. At 
every stage, Sheppard has proven himself a defendant committed to the legal 
process, not a risk of flight. 
 
B. 
Sheppard’s Appeal Will Raise Substantial Questions 
The government rests its case for imprisonment pending appeal on the absence 
of substantial questions. But it starts by attacking a strawman. The government 
asserts that “[j]ust because” the law is in flux does not mean a particular conviction 
will present a substantial question on appeal. DE 245 at 4. That is probably right. 
But it’s not Sheppard’s argument. Sheppard does not argue that “the existence of 
new case law in the areas of wire fraud and aggravated identity theft” necessarily 
means that his appeal will present a substantial question. Id. at 5. Rather, Sheppard’s 
argument is that his convictions are doubtful (if not clearly incorrect) under the legal 
principles articulated in those cases. 
Take Sheppard’s aggravated identity theft convictions. Dubin v. United 
States, 599 U.S. 110 (2023), holds that the defendant’s use of someone’s means of 
identification must be at the crux of what makes his underlying conduct criminal. 
The parties dispute what that legal test means and how it applies to this case. The 
government takes the view that any conduct that lends credibility to a fraud must be 
at the crux of the fraud. Sheppard reads Dubin differently. In Sheppard’s view, 
Dubin requires the Court to ask whether a “key mover” in Sheppard’s wire fraud 
was his use of Cupersmith’s identity—whether Cupersmith’s identity played a 
“central role” in the fraud. Dubin, 599 U.S. at 122-23. In the words of United States 
v. Gladden, 748 F.4th 1232 (11th Cir. 2023), whether Sheppard’s use of 
Cupersmith’s identity “directly enabled” him to obtain PPP loans to which he was 
not entitled. Id. at 1245-46. Those questions answer themselves.  
Case 1:22-cr-20290-BB   Document 249   Entered on FLSD Docket 05/31/2024   Page 4 of 7

5 
As the government admits, the wire fraud here centered on the provision of 
“materially false information about his businesses, wages and revenues.” DE 245 at 
7. On the government’s (contested) view of the evidence, Sheppard’s use of 
Cupersmith’s identity might have “facilitated” that fraud by making it more likely 
to succeed or even may have been the “but-for cause of its ‘success.’” Dubin, 
599 U.S. at 131 (“facilitation” or but-for cause not enough). But it was not a “key 
mover” in the fraud, did not play a ”central role” in the fraud, and did not “directly 
enable” Sheppard to obtain the PPP loans. The important point here, however, is not 
that Sheppard’s reading of Dubin and Gladden is correct (it is); but rather that the 
Eleventh Circuit could agree with Sheppard.  
 The same is true for Sheppard’s wire fraud convictions. The government 
contends that United States v. Takhalov, 827 F.3d 1307 (11th Cir. 2016), is factually 
distinguishable, but Sheppard has never argued that this case is on all fours with 
Takhalov factually. Instead, Sheppard argues that he is innocent of wire fraud under 
the legal rule Takhalov articulated—namely, that a defendant is innocent of wire 
fraud where the alleged victim gets everything it bargained for. The government 
suggests that the lending banks did not get everything they bargained for because 
part of the “bargain” financially was a borrower who was eligible to participate in 
PPP. DE 245 at 6. But it has never cited any evidence supporting that theory nor has 
it offered a cogent explanation for why that would be the case—after all, the banks 
were financially indifferent to Sheppard’s businesses’ eligibility to participate in 
PPP because the banks got processing fees and interest regardless, and they would 
have loaned the same money to someone else on the same terms if they had not 
loaned it to Sheppard. 
The government claims that United States v. Watkins, 42 F.4th 1278 (11th Cir. 
2022), supports its position, but Watkins is clearly distinguishable, as Sheppard has 
explained in opposition to the government’s notice of supplemental authority. See 
Case 1:22-cr-20290-BB   Document 249   Entered on FLSD Docket 05/31/2024   Page 5 of 7

6 
DE 230.2 In the commercial context, lenders have a financial (i.e., property) interest 
“in knowing to whom they are loaning money and for what purpose.” Watkins, 
42 F.4th at 1286. Not so here. The banks had no financial (i.e., property) interest in 
knowing, for example, whether workers paid by Sheppard’s companies were 
technically “employees” who earned “W2” wages or were instead “independent 
contractors,” because the banks stood to gain financially from lending to Sheppard 
and would have lent on the same terms to someone else if not to him. Not all “loan 
context[s]” are the same. DE 245 at 6. While the government proclaims that “[o]f 
course” Sheppard’s representations “went to the nature of the bargain,” DE 245 at 
6, on these facts, the Eleventh Circuit easily could disagree, which is all that matters 
for purposes of this motion. 
  
II. 
IN THE ALTERNATIVE, THIS COURT SHOULD ALLOW 
SHEPPARD TO SELF-SURRENDER 
If this Court is disinclined to allow Sheppard to remain out-of custody—but 
under the Probation Office’s supervision—all the way through the appeal, Sheppard 
requests that this Court at least allow him to self-surrender. The government offers 
no real argument in opposition, other than to cross-reference its suggestion that 
Sheppard is not a flight risk because he faces a lengthy prison sentence. See DE 245 
at 8. The government’s argument is even weaker here. There is no basis to conclude 
that Sheppard would flee during the few weeks it would take for the Eleventh Circuit 
to consider whether to allow him to remain under the Probation Office’s supervision 
(rather than in custody) pending appeal, all while the Bureau of Prisons designates 
Sheppard to the facility where he would serve any sentence imposed by the Court. 
 
2 The government cited Watkins in its notice of supplemental authority but failed to 
explain the significance of that decision. See DE 228. Having now belatedly availed 
itself of that opportunity, it is clear Watkins is inapposite. 
Case 1:22-cr-20290-BB   Document 249   Entered on FLSD Docket 05/31/2024   Page 6 of 7

7 
And there are practical reasons to allow Shepard to self-surrender, including a 
reduction in expenses that will ultimately be borne by the taxpayers. 
 
 
 
 
 
Respectfully submitted,  
 
 
 
 
 
BLACK SREBNICK  
 
 
 
 
 
201 South Biscayne Boulevard, Suite 1300   
 
 
 
 
 
Miami, Florida 33131 / Tel (305) 371-6421   
 
 
 
 
 
By:  /s Howard Srebnick  
 
 
 
 
 
Howard Srebnick  
 
 
 
 
 
  Florida Bar No. 919063  
 
 
 
 
 
  HSrebnick@RoyBlack.com 
 
 
 
 
 
 
O’MELVENY & MYERS 
 
 
 
 
 
Jeffrey L. Fisher (admitted pro hac vice) 
 
 
 
 
 
Jason Zarrow (admitted pro hac vice) 
 
 
 
 
 
 
 
 
 
 
 
NELSON MULLINS 
Jayne C. Weintraub 
 Florida Bar No. 320382 
Jonathan Etra  
 Florida Bar No. 686905 
Christopher Cavallo  
 Florida Bar No. 0092305 
 
Case 1:22-cr-20290-BB   Document 249   Entered on FLSD Docket 05/31/2024   Page 7 of 7

File and source

File

gov.uscourts.flsd.615773.249.0.pdf

Size

196,870 bytes

SHA-256

80439c6434dc6923f94e93290f6f821c30f523831386ec4f95668a8a7669971a

Our copy

gov.uscourts.flsd.615773.249.0.pdf

Original

PACER (login required)