Robert ‘Bobby’ Dominic has lived a lifetime on Grand Avenue, mostly out of the public eye. He is known for his association with Richard’s Bar, a tavern where smoking laws don’t seem enforced. Dominic is reputed to have ties to the Outfit, going back years. The FBI identified him as a former driver for infamous mob boss Joey “The Clown” Lombardo. Reports suggested Dominic was involved in pornography and gambling operations for the syndicate. While maintaining connections with current mob leaders, Dominic has never been widely known. He lacks a significant criminal record. Despite numerous FBI investigations taking down old bosses, Dominic remains a presence at Richard’s Bar, which is owned by his sister on paper.
Dominic’s recent appearance at Dirksen U.S. Courthouse to plead guilty to a tax charge stirred minimal media attention. The hearing appeared ordinary, except for the presence of FBI agents from the public corruption squad. U.S. District Judge Elaine Bucklo raised questions about the plea deal that included going directly to sentencing and a short probation recommendation. The typical process involves a presentence investigation and report suggesting a sentence. However, Dominic’s case bypassed this step due to his age, first-time offender status, and the determination of no actual tax loss to the IRS.
Judge Bucklo acquiesced to the deal, avoiding a trial scheduled for later. Dominic, dressed in a gray suit and light green tie, spoke little and struggled with hearing during the 30-minute proceeding. When asked about his education, Dominic mentioned only two months of high school. He shared his past work involved assisting his father at a tavern and rooming house, referring to the Acacia Hotel linked to Richard’s Bar. Dominic will have completed supervision early next year, due to his time on bond counting towards his probation.
After the hearing, Dominic left the courthouse with lawyer Joel Rabb, who later refused to comment. Lead attorney Gabrielle Sansonetti also offered no remarks. Dominic conceded in his plea agreement with prosecutors that he instructed his wife, named only as Individual B, to prepare tax returns in 2021 and 2022 that omitted his ownership interest. The agreement stated Company A paid corporate taxes punctually, but Dominic admitted that ownership details were crucial for IRS assessments and tax collections.
The plea stands in contrast to the charges last year. Dominic was alleged to have obtained money from sweepstakes gaming companies through a fake entity owned by his past girlfriend. A month after her 2020 death, Dominic allegedly established another sham company via another woman to continue receiving payments. The charges indicated Dominic received over $1.2 million from sweepstakes gaming businesses and failed to file tax returns for that income.
During court proceedings, Rothblatt noted that Company A had settled all due income taxes, and any owed personal taxes by Individual B were paid in subsequent years. Dominic’s case is a spin-off of a major investigation into sweepstakes gaming machines affecting former state Rep. Luis Arroyo and businessman James Weiss, married to Maria “Toni” Berrios, daughter of former state Rep. Berrios. Prosecutors, in Weiss’ sentencing memo, detailed ties with mob hitman Frank “The German” Schweihs, whom Weiss approached for his massage parlors under threat.
Weiss’ association was confirmed in wiretaps indicating partnership with a reputed mob associate. Schweihs, charged in the Family Secrets mob case and evading arrest, allegedly helped Weiss through Dominic. This partnership continued, described by Joseph Weiss in prosecutorial records as Dominic being a straightforward gangster. Schweihs died awaiting trial in 2008, and Joseph Weiss was charged in 2023 for lying about his brother’s mob connections, resulting in a two-month jail sentence.
Tribune reports connected Weiss’ sweepstakes company, V.S.S., to ex-Chicago police officer John Adreani, fired for associating with drug traffickers. An associate, Anthony DeMarco, registered a sweepstakes firm using the Grand Avenue address housing Richard’s and La Scarola restaurant.
Weiss was convicted in 2023 on seven counts involving bribery, fraud, and false statements. He agreed on paying monthly $2,500 bribes to influence gambling legislation, unknowingly dealing with FBI collaborator Sen. Terry Link. Link’s testimony aids hopes for leniency in his own tax conviction case. Weiss, sentenced to 5½ years, currently resides at a Chicago-area halfway house.
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