Brother of businessman convicted of bribing state officials pleads guilty to lying to feds about Chicago mob connections

The brother of James Weiss, the politically connected business owner convicted of bribing two state elected officials, pleaded guilty Monday to lying to federal investigators about his brother’s mob contacts, including connections to notorious Outfit hit man Frank “The German” Schweihs.

Joseph “Joey” Weiss, 44, of Oak Lawn, entered his plea to one count of lying to the FB. The charge carries up to five years in prison, but preliminary sentencing guidelines call for only up to six months behind bars for Weiss, who has no criminal history. Probation is also an option.

U.S. District Judge Matthew Kennelly set a sentencing hearing for Aug 12.

The charges against Weiss, which were made public in October, brought new mob intrigue to a case that already had elements of political corruption, a state senator-turned-government mole, a corrupt former police officer and the shady world of sweepstakes gaming machines.

According to the six-page indictment, Weiss collected revenue and performed other services for his brother’s sweepstakes gaming business, which operated the quasi-legal machines that look like video poker terminals but are not regulated by the state.

In October 2020, the brother, James Weiss, who is the son-in-law of former Cook County Assessor Joseph Berrios, was charged in a superseding indictment with attempting to pay off two state legislators to pass a bill beneficial to his sweepstakes gaming company and then lying about it to two FBI agents.

The next year a new federal grand jury investigation was initiated to determine whether James Weiss, his company or another co-owner of the company, identified only as Individual B, had any ties to the Chicago Outfit, and in particular Schweihs, the mob hit man who was charged in the landmark Family Secrets case more than a decade earlier, according to Joseph Weiss’ 15-page plea agreement with prosecutors.

Schweihs, who according to authorities spent decades as a reputed enforcer for the mob’s Grand Avenue street crew, died of cancer in 2008 while awaiting trial.

In January 2022, more than a year after his brother’s indictment, Joseph Weiss lied to FBI and IRS agents in an interview when he denied knowing anyone who used to do business with Schweihs, including both his brother and Individual B, according to the plea agreement.

After being told that a federal grand jury was examining the connections, Weiss allegedly told investigators, “I swear I’ve been honest. I think I’ve given you what I know,” the charges alleged.

But it turned out that Joseph Weiss had been caught on a federal wiretap saying his brother was “good friends” with Schweihs and once went to him for protection for his massage parlors being threatened by other gangsters.

Joseph Weiss was also recorded telling someone his brother had partnered up with “a known longtime mob associate,” Individual B, after Weiss had reportedly gone to Schweihs for help, according to prosecutors.

“Yeah, well, Jimmy and Frank were good friends, and some Russians were muscling Jimmy, but Frank was on the run,” Joseph Weiss allegedly told an unidentified person in a wiretapped call. “Frank was in hiding and Jimmy called Frank and says, hey man, these guys just busted up my (expletive store). Scared the (expletive) out of the girls, this and that, you know, I need your help, where the (expletive) are you?”

At the time, Schweihs had been charged in the Family Secrets mob case and was on the run. According to the brother’s story, The German told Weiss, “‘Jim, I’m underground right now … but I’ll have someone call you right back.’”

“Somebody called Jimmy” and told him to go see Individual B, who “straightened it all out,” Joseph Weiss said, according to the transcript of the call that was detailed in James Weiss’ sentencing papers. “Ever since then, they’re partners on everything. The problem is (Individual B)’s like a gangster but he’s an honest guy. If you’re his friend, you’re his friend.”

Prosecutors have called the description of Individual B as a gangster “an apt one.”

In a separate undercover recording “Individual B admitted that James Weiss ‘is with me,’ referencing their joint involvement with gaming machines,” prosecutors said in their sentencing filing in that case.

The filing also alleged that Individual B’s now-deceased girlfriend was a partner in one of James Weiss’ gambling businesses and received hundreds of thousands of dollars in payments from him.

James Weiss’ attorneys have denied that Weiss has any connection to Schweihs, saying he had never met him and never did business with him.

Weiss, who was sentenced by U.S. District Judge Steven Seeger in October to 5 ½ years in prison, is at a federal prison facility in Minnesota and due to be released in August 2028, records show.

The Tribune has previously reported that Weiss’ business partners used a complex web of limited liability company names that often shared addresses, including one called Mac-T that used an address of 723 W. Grand Ave. in Chicago, which is a single-room occupancy hotel in the same building that houses the Italian restaurant La Scarola and Richard’s Bar.

Richard’s is owned, on paper at least, by the sister of Robert “Bobby” Dominic, a reputed Outfit associate who, according to FBI and Chicago records, ran pornography and gambling interests for the Grand Avenue crew, which was headed by legendary mobster Joseph “The Clown” Lombardo.

Meanwhile, records obtained by the Tribune show the same federal grand jury looking into Weiss’ mob connections is also interested in Dominic.

Dominic has not been charged and couldn’t immediately be reached for comment.