Brother of convicted businessman set to plead guilty to charges of lying to FBI

The brother of a clout-heavy businessman is poised to plead guilty to charges he lied to federal investigators when asked about his brother’s ties to a mob enforcer.

Joseph Weiss, whose brother, James Weiss, was convicted of bribing two state legislators to help pass legislation that would have benefited his sweepstakes machine business, has reached a plea deal with prosecutors, according to court records. U.S. District Judge Matthew Kennelly has set a May 20 date for a change-of-plea hearing.

James Weiss’ attorneys have denied any connection to the mob, though at his sentencing hearing, federal prosecutors cited his alleged Outfit connections as a reason for giving him a longer prison term — based in part on recorded conversations in which Joseph Weiss said that his brother was “great friends” with Outfit hitman Frank “The German” Schweihs. James Weiss is politically well-connected, as the husband of ex-state Rep. Toni Berrios and the son in-law of former Democratic Cook County Assessor Joseph Berrios.

Joseph Weiss had worked for his brother’s business, which was at the heart of the bribery scheme that sent James Weiss to prison. James Weiss was sentenced to 5½ years after he was convicted of making payoffs to former state Rep. Luis Arroyo and former state Sen. Terry Link, in exchange for their help passing legislation that would have fully legalized sweepstakes machines. The machines, which resemble video gambling machines, operate in a legal gray area and Weiss had hoped to have them made legal with support from Link and Arroyo.

Nearly two years after his brother was indicted in 2020, Joseph Weiss was questioned by federal agents who were apparently probing James Weiss’ alleged ties to the Chicago Outfit. Asked if he knew anyone with connections to the crime syndicate, Joseph Weiss said no. Asked specifically if he knew anyone who had a relationship with Frank “The German” Schweihs, a mob hitman who died in 2008, Weiss said no. Asked if he'd heard stories about how his brother and another businessman came to know Schweihs, he replied no.

“I swear I’ve been honest. I think I’ve given you what I know,” Joseph Weiss told investigators, according to his indictment.

But in a wiretapped call recorded in 2018, Joseph Weiss had described his brother and Schweihs as “good friends” who were “partners on everything."

In one taped conversation, Joseph Weiss recalled how his brother had reached out to Schweihs for muscle after “some Russians” busted up one of his businesses. Schweihs, who at the time was under indictment in the Family Secrets case that also targeted Outfit bosses Joey “The Clown” Lombardo and Frank Calabrese, was on the run at the time.

“Jimmy and Frank were good friends,” Joseph Weiss said in that recorded conversation, according to federal prosecutors. “And some Russians were muscling Jimmy, but Frank was on the run. Frank was in hiding, and Jimmy called Frank and said, ‘Hey,’ ’cause they were partners. And Jimmy says, ‘Hey, man, these guys just busted up my f---ing store. Scared the f--- out of the girls, this and that, you know, I need your help; where the f--- are you?’”

“‘Jim, I’m underground right now,” Schweihs responded, according to Joseph Weiss. “But I’ll have someone call you right back.'”

According to a transcript of the call in court records, while on the lam, Schweihs contacted someone who “straightened it all out.”

“Ever since then, they’re partners on everything."