Robert “Bobby” Dominic has spent a lifetime on Grand Avenue, but always seemingly behind the scenes.
Known for his connections to Richard’s Bar, the old-school tavern where the city’s smoking ordinances never seem to be enforced, Dominic has reputed Outfit ties that go back many years. FBI records reported he once was a driver for notorious boss Joey “The Clown” Lombardo. The Tribune has reported he allegedly ran pornography and gambling interests for the syndicate. And sources say he has stayed close with current mob leadership.
But Dominic has never been a household name. He has no notable criminal record. And as the old bosses were felled by a series of FBI investigations, he’s continued to quietly hold court at Richard’s, which is owned by his sister — on paper at least.
So it was fitting that when Dominic appeared at the Dirksen U.S. Courthouse on Friday to plead guilty to a tax charge, there was no big media stir. To the outside observer, the hearing for the soft-spoken man with the graying mustache may have seemed like any other, save for the FBI agents from the public corruption squad sitting in the back.
Then the judge looked closely at the deal that had been struck, which included a provision to proceed straight to sentencing and recommend a short term of probation.
“This is unusual,” U.S. District Judge Elaine Bucklo said at the outset of the hearing. “I need to know about what this is.”
Normally, a defendant who pleads guilty in federal court submits to what is known as a presentence investigation, where court officials do a deep dive into his background and the conduct related to the conviction and write a report recommending a sentence.
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But that had all been waived for Dominic. Why?
Assistant U.S. Attorney Richard Rothblatt told the judge Dominic was 72 years old, a “first-time offender,” and that his office had determined there had been no actual tax loss to the IRS, all factors in the decision to end the case in this manner.
“Well there must have been something to make you decide to indict him,” Bucklo said.
In the end, Bucklo went along with the deal, which scuttled a trial that had been set for later this year. Dominic, dressed in a gray suit and light green tie, spoke little during the 30-minute hearing, and had to have the judge repeat herself several times because of hearing issues.
When the judge asked how far he went in school, Dominic said, “Two months of high school.” He’s been retired for years, he said. So what did he do when he was working?
“I would help my father at the tavern and the rooming house,” Dominic told the judge, an apparent reference to the Acacia Hotel, a single-room occupancy facility connected to Richard’s Bar.
Under the terms of the deal, the year and a half Dominic has spent free on bond while the case was pending will count toward his two years of probation. That means he’ll be free and clear of any court supervision by early next year.
Minutes after the hearing ended, Dominic walked out of the Dirksen U.S. Courthouse flanked by one of his lawyers, Joel Rabb, and got into a car without comment. Reached by phone later in the day, Rabb said, “I have nothing to say. Have a great day,” then hung up.
His lead attorney, Gabrielle Sansonetti, also declined to comment.
Dominic admitted in his bare-bones plea agreement with prosecutors that he directed his wife, identified only as Individual B, to prepare corporate tax returns in 2021 and 2022 for Company A that failed to identify his ownership interest.
The agreement stated Company A paid all applicable corporate taxes on time, but that Dominic admitted “the ownership information for Company A was material to the IRS’s ability to, among other things, ascertain, compute, assess, and collect tax revenue.”
Those admissions pale in comparison to what was alleged in the original charges brought last year. According to that indictment, Dominic was 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 and continued to receive payments from the sweepstakes businesses, according to the original indictment, which has now been dismissed.
The indictment listed payments Dominic allegedly received from the sweepstakes gaming companies totaling more than $1.2 million. The charges also alleged Dominic failed to file personal tax returns reflecting any of that income.
In court Friday, Rothblatt said prosecutors determined Company A had paid all applicable income taxes to the IRS on time, and that any personal income taxes that had been owed by Individual B were paid up in following years.
The case against Dominic was 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 the son-in-law of former Cook County Democratic Party boss Joe Berrios.
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, Joseph, was caught on an FBI wiretap saying that Weiss had partnered with “a known longtime mob associate” after Weiss had reportedly gone to Schweihs for help. 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. The problem is (Dominic’s) like a gangster but he’s an honest guy. If you’re his friend, you’re his friend.”
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.
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. He pleaded guilty and was sentenced to two months in jail.
The Tribune has previously reported that James Weiss’ sweepstakes company, V.S.S., was connected to a former Chicago police officer, John Adreani, who was fired from the Chicago Police Department in 2015 for associating with a major drug trafficker.
Another associate, Anthony DeMarco, incorporated a sweepstakes business using the Grand Avenue address for the building that houses Richard’s as well as the Italian restaurant La Scarola, records show.
James Weiss was convicted by a jury in 2023 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 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 testified over two days about his undercover role, receiving a break at sentencing for his own tax conviction.
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James Weiss was sentenced in October 2023 to 5½ years in prison. He’s currently assigned to a Chicago-area halfway house, records show.