Robert “Bobby” Dominic has spent much of his life on Grand Avenue, mostly out of the public eye. Known for his connections to Richard’s Bar, an old-school tavern often ignoring city smoking laws, Dominic is reputed to have connections with the Outfit. His history includes serving as a driver for notorious boss Joey “The Clown” Lombardo, according to FBI records. The Tribune reported he allegedly managed pornography and gambling ventures for the syndicate. Despite maintaining close ties with current mob leadership, Dominic is not a household name, lacking a significant criminal record. As older bosses fell due to FBI investigations, Dominic continued to hold court at Richard’s, which legally belongs to his sister.
On Friday, Dominic appeared at the Dirksen U.S. Courthouse, pleading guilty to a tax charge without attracting substantial media attention. The hearing for this soft-spoken man with a graying mustache seemed ordinary, apart from FBI agents from the public corruption squad in attendance. U.S. District Judge Elaine Bucklo highlighted the unusual nature of the deal struck, which included skipping the presentence investigation and proceeding directly to sentencing, recommending probation. “This is unusual,” Judge Bucklo noted. She asked for details about the situation, normally involving a comprehensive investigation into the defendant’s background.
Assistant U.S. Attorney Richard Rothblatt informed the judge about Dominic’s age, 72, his status as a “first-time offender,” and noted no actual tax loss to the IRS. These factors guided the decision to end the case promptly. “Well there must have been something to make you decide to indict him,” Judge Bucklo remarked. Ultimately, Bucklo agreed to the deal, preventing a trial later this year. Dominic, dressed in a gray suit and light green tie, spoke little during the hearing and had difficulty hearing the judge. He shared his educational background as “Two months of high school” and mentioned retirement. When asked about his past work, Dominic replied, “I would help my father at the tavern and the rooming house,” likely referring to the Acacia Hotel connected to Richard’s Bar.
Under the agreement’s terms, he will be free from court supervision by early next year, as the year and a half he spent free on bond counts towards his two-year probation. After the hearing ended, Dominic exited the courthouse with his lawyer, Joel Rabb, without comment. Later, Rabb declined to speak further when reached by phone. The lead attorney, Gabrielle Sansonetti, also refrained from commenting.
Dominic admitted, in a plea agreement, directing his wife to prepare corporate tax returns without disclosing his ownership interest for Company A in 2021 and 2022. While Company A paid all corporate taxes timely, Dominic acknowledged ownership information was crucial for the IRS in assessing tax revenue. These admissions were less severe than the initial charges. The indictment last year accused Dominic of receiving hundreds of thousands from sweepstakes gaming companies through a sham entity owned by his then-girlfriend. After her death in 2020, Dominic allegedly established another bogus company and continued receiving payments.
The dismissal of charges against Dominic was part of an investigation into corrupt sweepstakes gaming operations that implicated former state Rep. Luis Arroyo and businessman James Weiss. Prosecutors indicated in Weiss’ case that Weiss sought help from mob hitman Frank “The German” Schweihs before partnering with Dominic. Dominic was portrayed as an honest, yet mob-associated figure, resolving disputes for Weiss. Schweihs, a long-time enforcer of the mob’s Grand Avenue street crew, died in 2008 while facing charges.
Joseph Weiss, a collaborator, faced charges for lying to federal investigators, eventually pleading guilty and receiving two months in jail. James Weiss’ sweepstakes company had connections with former Chicago police officer John Adreani, fired for associating with a major drug trafficker. Another associate used the Grand Avenue address for a sweepstakes business connected to Richard’s Bar and La Scarola, as records revealed.
James Weiss faced conviction for bribery, wire fraud, and other charges, including bribing state officials to shape gambling legislation favoring his sweepstakes business. Weiss didn’t realize state Sen. Terry Link, involved, cooperated with the FBI. Link, seeking leniency for his federal tax conviction, provided testimony against Weiss, leading to a 5 ½ year sentence. Weiss remains at a Chicago-area halfway house, according to reports.