A mob-connected Chicago businessman has been indicted on tax evasion charges alleging he had a hidden interest in a sweepstakes gaming company run by the now-imprisoned son-in-law of Joe Berrios, the former Cook County assessor.
Robert “Bobby” Dominic, 71, a longtime associate of the Outfit’s Grand Avenue crew known for his connections to Richard’s Bar on the Near West Side, was charged in a five-count indictment made public Tuesday in U.S. District Court with tax evasion and failure to file tax returns.
An arraignment date has not been set. Dominic’s attorney could not immediately be reached for comment.
The indictment alleged that from 2014 to 2020, Dominic was secretly paid hundreds of thousands of dollars from two sweepstakes gaming companies through a sham entity owned by his then-girlfriend.
A month after his girlfriend died in January 2020, Dominic allegedly set up another phony company through another woman, identified only as Individual B, and continued to receive payments from the sweepstakes businesses, according to the indictment.
On March 30, 2021, the stock certificate for Sham Company B “was amended to reflect that all shares were to transfer to Dominic upon Individual B’s death,” the indictment stated.
Last fall, the U.S. attorney’s office subpoenaed Individual B to appear before a federal grand jury investigating Dominic, and sent a letter to her attorney indicating she would be compelled to testify through a grant of immunity, according to the indictment.
A few days before her scheduled grand jury appearance on Oct. 7, 2024, however, Individual B, who at the time was about 80 years old, agreed to marry Dominic in order to prevent her testimony, the indictment stated.
The charges also allege Dominic failed to file tax returns reflecting any of the income he made from the sweepstakes interests.
The charges against Dominic are an offshoot of a bombshell investigation into the shady world of sweepstakes gaming machines that brought down former state Rep. Luis Arroyo and businessman James Weiss, who is married to Berrios’ daughter, former state Rep. Maria “Toni” Berrios.
The case also had mob connections simmering in the background. The Tribune first reported last year that the grand jury sent a subpoena to the Illinois Department of Insurance on July 28 seeking applications, communications and other records involving a state Comprehensive Health Insurance Plan in Dominic’s name.
Around that same time, federal prosecutors alleged in a sentencing filing in Weiss’ criminal case that he was allegedly “good friends” with notorious mob hit man Frank “The German” Schweihs and once went to him for protection for his massage parlors being threatened by other gangsters.
Weiss’ brother, in fact, was caught on an FBI wiretap telling someone Weiss had partnered with “a known longtime mob associate” after Weiss had reportedly gone to Schweihs for help.
Details included in the new charges against Dominic reveal that he was the associate referred to on the recording.
“Yeah, well, Jimmy and Frank were good friends, and some Russians were muscling Jimmy, but Frank was on the run,” the brother, Joseph Weiss, told an unidentified person in the 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 landmark 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 Dominic, who “straightened it all out,” Joseph Weiss said, according to prosecutors.
“Ever since then, they’re partners on everything,” Joseph Weiss said. “The problem is (Dominic’s) like a gangster but he’s an honest guy. If you’re his friend, you’re his friend.”
Prosecutors called the description of Dominic as a gangster “an apt one.” In a separate undercover recording, Dominic admitted that James Weiss ‘is with me,’ referencing their joint involvement with gaming machines,” the filing stated.
“Insofar as (James) Weiss seeks to portray himself as a community-minded and otherwise law-abiding individual, his longtime partnership with (Dominic) and his own brother’s recording discussing his prior association with his ‘good friend,’ mob killer Frank Schweihs, demonstrates otherwise,” prosecutors wrote.
The filing also alleged that Dominic’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.
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.
Weiss’ brother, Joseph Weiss, was charged in 2023 with lying to federal investigators about his brother’s reputed mob ties, including his previous contacts with Schweihs and Dominic.
James Weiss’ attorney, Ilia Usharovich, said his client had no ties at all to Schweihs.
“Jim denies ever speaking to Mr. Schweihs, ever meeting with Mr. Schweihs and ever doing business with Mr. Schweihs,” Usharovich said.
The Tribune has previously reported that James Weiss’ sweepstakes company, V.S.S., was connected to a former Chicago police officer, John Adreani, through a complex web of corporations, many of which list the same address in a south suburban strip mall as their headquarters.
Adreani was fired from the Chicago Police Department in 2015 for associating with a major drug trafficker after he was captured on a wiretap discussing gambling and drinking excursions and real estate ventures with him, according to Chicago Police Board records.
Adreani was not charged; however, his name came up several times during James Weiss’ trial.
Another one of Weiss’ business entities, Mac-T Retail LLC, which was formed in 2015, shares the same address in the 800 block of Sibley Boulevard in Dolton with V.S.S., state records show.
At least three companies that include “Mac-T” in their titles appear to be linked, according to state records. The first of them, Mac-T LLC, was organized by Anthony DeMarco of River Grove in 2014 and was also registered to the Sibley Boulevard address.
DeMarco originally incorporated Mac-T using 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.
La Scarola was the scene of a 2012 lunch meeting with top Grand Avenue crew members that led to the FBI sting of hit man Steve Mandell, who was plotting, among other things, to kidnap, rob and murder a mobbed-up strip club owner.
Richard’s is owned, on paper at least, by the sister of 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.
James Weiss was convicted by a jury in June of seven counts of bribery, wire fraud, mail fraud and making false statements. The charges alleged Weiss then agreed to pay monthly $2,500 bribes to get language helping his sweepstakes business added to state gambling legislation, first to state Arroyo and later to state Sen. Terry Link, who was a chief sponsor of the gambling bill in the Senate.
Arroyo and Weiss didn’t know that Link, a Vernon Hills Democrat, was cooperating with the FBI. Link, who is hoping for a break in his own federal tax conviction in exchange for his cooperation, testified over two days about his undercover role.
Arroyo, meanwhile, pleaded guilty to bribery for his role in the scheme but did not agree to cooperate with prosecutors. U.S. District Judge Steven Seeger sentenced Arroyo to nearly five years in prison last year, calling him a “corruption superspreader.”
Arroyo was released to a halfway house late last year, federal prison records show.
James Weiss was sentenced in October 2023 to 5 ½ years in prison. He’s currently serving his term in Leavenworth, Kansas, and is due to be released in March 2027, records show.
Joseph Weiss pleaded guilty last year and was sentenced to two months in jail.
jmeisner@chicagotribune.com
