Robert “Bobby” Dominic, a long-standing figure on Grand Avenue, has long stayed in the background. Noted for his association with Richard’s Bar, where city smoking laws are often overlooked, Dominic is believed to be connected to organized crime. The FBI recorded him as once working as a driver for famed mob boss Joey “The Clown” Lombardo. The Tribune also reported that he controlled pornography and gambling operations for the syndicate and maintained ties with current mob leaders.
Despite this, Dominic’s name is not widely known, due in part to his lack of a significant criminal record. As previous mob leaders have fallen to FBI actions, Dominic has continued his quiet presence at Richard’s, legally owned by his sister.
Dominic recently surfaced at the Dirksen U.S. Courthouse, intending to plead guilty to a tax charge. The event drew little media attention, though FBI agents were present. During the hearing, U.S. District Judge Elaine Bucklo scrutinized the plea deal, which proposed moving straight to sentencing with a recommendation for probation. Bucklo expressed curiosity about the unusual nature of the deal.
This is unusual. I need to know about what this is.
Typically, a guilty plea in federal court involves a report reviewing the defendant’s background and the crime, which was bypassed for Dominic. Assistant U.S. Attorney Richard Rothblatt confirmed Dominic’s age, status as a first-time offender, and the absence of an IRS tax loss influenced the decision.
Judge Bucklo eventually approved the deal, avoiding a trial set for later this year. Dominic, in a gray suit and light tie, spoke little and faced difficulty hearing the proceedings. When asked about his education, he mentioned having only two months of high school.
The terms allowed Dominic’s previous bond period to count toward his probation, freeing him from supervision by early next year. Following the hearing, Dominic left the courthouse with his lawyer but did not comment.
Dominic’s plea agreement acknowledged instructing his wife, named only as Individual B, to create company tax returns in 2021 and 2022 without declaring his ownership. Although the company paid taxes promptly, the plea admitted that the ownership information was crucial for the IRS to manage tax affairs accurately.
The initial charges drawn up last year alleged Dominic earned significant sums through two gaming companies using a sham entity under his then-girlfriend’s name. A $1.2 million income was allegedly concealed from tax returns.
Prosecutors later found Company A had met tax obligations, and Individual B had resolved past tax debts. The charges sprout from a broader investigation of sweepstakes gaming machines that led to revelations involving former state Rep. Luis Arroyo and businessman James Weiss.
Weiss, reportedly linked to mob enforcer Frank “The German” Schweihs, once sought protection from him. Schweihs instructed Weiss to contact Dominic, who resolved the issue, according to an FBI wiretap story. Schweihs passed life awaiting trial in 2008.
Joseph Weiss faced charges for concealing his brother’s mob connections, to which he pled guilty, serving a two-month sentence. The Tribune connected James Weiss’ gaming company, V.S.S., to former Chicago police officer John Adreani and associate Anthony DeMarco, linking to the address housing Richard’s Bar.
In 2023, Weiss faced convictions of bribery and fraud for attempting to influence gambling legislation, unaware of state Sen. Terry Link’s cooperation with federal authorities. His sentence amounted to 5 ½ years, with current residence at a Chicago-area halfway house.