United States v. James Weiss

CourtCourt of Appeals for the Seventh Circuit
DecidedAugust 28, 2025
Docket23-3094
StatusPublished

This text of United States v. James Weiss (United States v. James Weiss) is published on Counsel Stack Legal Research, covering Court of Appeals for the Seventh Circuit primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
United States v. James Weiss, (7th Cir. 2025).

Opinion

In the

United States Court of Appeals For the Seventh Circuit ____________________ No. 23-3094 UNITED STATES OF AMERICA, Plaintiff-Appellee, v.

JAMES T. WEISS, Defendant-Appellant. ____________________

Appeal from the United States District Court for the Northern District of Illinois, Eastern Division. No. 1:19-cr-00805-2 — Steven C. Seeger, Judge. ____________________

ARGUED JANUARY 15, 2025 — DECIDED AUGUST 28, 2025 ____________________

Before ROVNER, JACKSON-AKIWUMI, and MALDONADO, Circuit Judges. ROVNER, Circuit Judge. Sweepstakes machines are a form of gambling machine. In 2018, sweepstakes machines oper- ated in a legal gray area; they were neither clearly legal nor clearly illegal under existing Illinois law. James Weiss’s com- pany manufactured sweepstakes machines and, as a result, Weiss had an interest in ensuring that sweepstakes machines were clearly legal under Illinois law. To accomplish this goal, 2 No. 23-3094

Weiss attempted to bribe two state legislators, Luis Arroyo and Terrance Link, to pass legislation favorable to sweep- stakes machines. Unbeknownst to Weiss, however, Link was cooperating with federal agents, ultimately leading to Weiss’s conviction for wire fraud, mail fraud, and bribery after a jury trial. On appeal, Weiss challenges statements the district court admitted at trial, one of the jury instructions given at trial, and his sentence. Because we find no error by the district court, we affirm. I Beginning in fall 2018, Weiss’s company, Collage LLC, be- gan making monthly payments to Arroyo’s registered lobby- ing firm, Spartacus 3, LLC. In exchange, Arroyo became an extremely vocal supporter of sweepstakes legislation. He spoke in support of such legislation at gaming committee hearings, advocated for it during meetings with the Illinois General Assembly’s leadership, and approached other legis- lators to encourage them to pass sweepstakes legislation. In fact, Arroyo approached State Representative Robert Rita about sweepstakes legislation so frequently that State Repre- sentative Rita began avoiding Arroyo. These efforts failed, however, and gaming legislation was passed in June 2019 without any sweepstakes-related provisions. Undeterred, Weiss and Arroyo sought to have the gaming legislation amended through a “trailer bill,” which can mod- ify already-passed legislation. Doing so would require the support of State Senator Link, one of the sponsors of the gam- ing bill. No. 23-3094 3

On August 2, 2019, Arroyo and Weiss met with Link to ask him to support sweepstakes legislation during the “veto ses- sion”—which occurs in the fall—perhaps through the passage of a trailer bill. At the end of the meeting, Link asked to speak with Arroyo alone and asked Arroyo “what’s in it for me?” Arroyo explained that Link could be paid the “[s]ame way” he was “getting paid.” Arroyo also explained that the money could be sent to another individual, presumably to hide its intended recipient. After this meeting, Arroyo stayed in con- tact with Link, and a second meeting was arranged for Au- gust 22, 2019. In advance of the second meeting, the FBI directed Link to ask that any payments be made to “Katherine Hunter,” a fic- tious individual. Weiss drove Arroyo to the second meeting, but he remained in the car during the meeting. During the second meeting, Arroyo presented Link with a check from Collage LLC—Weiss’s company—with a blank payee line. As Arroyo took out the check, he said, “this is the jackpot” and asked for whom the check should be made out. At Link’s in- struction, Arroyo wrote “Katherine Hunter” on the payee line. Arroyo also presented Link with a draft of the legislation and Weiss’s business card. After the meeting, Weiss emailed the draft legislation to Link, and later, Weiss sent Link another check with “Katherine Hunter” named as the payee to an ad- dress that Link provided to Arroyo. By October 2019, FBI agents had obtained a search warrant for Weiss’s person and cell phone. After watching Weiss drive away from his home, the agents pulled Weiss over by activat- ing the lights on their vehicle. The agents then approached Weiss’s vehicle and said that they needed to speak with him, to which Weiss asked if he 4 No. 23-3094

should get out of his car. The agent responded by asking Weiss if he would join them in the FBI vehicle and told him that he was not under arrest. During the conversation, Weiss stated that he wanted to cooperate with the agents, but he made verifiably false state- ments to the agents. For example, he stated that he spoke with Katherine Hunter on the phone, and that he knew the check would ultimately go to Katherine Hunter before the August 22 meeting. This, of course, is not possible, as Link had not yet given Arroyo or Weiss Katherine Hunter’s name, and they could not have learned of it independently because she was fictitious. All told, the agents asked Weiss questions for approxi- mately 1 hour and 40 minutes. At the end of the interview, the agents executed the warrant for Weiss’s phone. Before trial, Weiss moved to suppress the statements he made to the FBI agents, claiming that he should have been given Miranda warnings before the conversation. The district court denied Weiss’s motion, as well as his motion for recon- sideration. Also before trial, the government moved to admit Arroyo’s recorded statements as coconspirator statements un- der Federal Rule of Evidence 801(d)(2)(E). The district court granted the government’s motion. At trial, the jury heard evidence about the alleged scheme. For example, the jury heard that Weiss’s company paid Ar- royo’s company from November 1, 2018 until October 1, 2019. The jury also heard that, during the same time, Arroyo be- came a very vocal and unrelenting advocate for sweepstakes legislation. Link testified about the August 2 and August 22 meetings, and federal agents testified about the materials sent No. 23-3094 5

by Weiss to Link and the conversation they had with Weiss before the execution of the search warrant. During the trial, the court held multiple jury instruction conferences. During the conferences, Weiss’s counsel objected to certain jury instructions. After about six days of trial and approximately four hours of deliberation, the jury found Weiss guilty on all charges. Weiss requested that his sentencing be delayed until after the enactment of certain changes to the Sentencing Guidelines, but the district court refused, explaining that it would apply its ordinary schedule, with a slight delay to accommodate de- fense counsel’s schedule. At sentencing, the district court explained that it had to “apply the guidelines as they exist today, today, the day of sentencing.” Sentencing Tr. 90:21–22. The district court con- tinued that it was “not supposed to apply future guidelines that may or may not go into effect” but it could “consider them” and it would “consider them for the Section 3553 [fac- tors].” Id. at 90:23–25. Later, the district court reiterated that it was imposing the guidelines as they were written at the time of sentencing, but that it would consider the upcoming changes when evaluating the § 3553(a) factors. The district court calculated the guidelines range to be 51 to 63 months, based on Weiss’s offense level and criminal his- tory category. Weiss sought leniency, but the government sought a sentence at the high end of the guidelines range, ar- guing that Weiss had shown no remorse. The district court asked both parties to explain Weiss’s cul- pability compared to that of Arroyo. The government argued that they were similarly culpable, but Weiss argued that only 6 No. 23-3094

a subset of the payments were bribes, and that Arroyo was more culpable as the public official. Before imposing the sentence, the district court discussed each of the § 3553(a) factors.

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