Mob-tied businessman gets 2 years probation for tax fraud linked to sweepstakes gaming industry

A man with ties to the Chicago Outfit was sentenced to two years probation Friday in a tax fraud case linked to the sweepstakes gaming industry.

Robert “Bobby” Dominic, 67, had been charged in 2025 with a conspiracy to defraud the United States, tax evasion and failure to file tax returns. But he only pleaded guilty Friday to a single charge of filing a false tax return during a hearing before U.S. District Judge Elaine E. Bucklo. The judge’s sentence includes credit for the time Dominic already spent on pretrial release.

His indictment alleged that he concealed income from federal authorities by having sweepstakes gaming companies pay him through the “sham” businesses. One of those sweepstakes companies was owned by James Weiss, who was sentenced to prison on bribery charges related to the sweepstakes industry.

Two sweepstakes companies paid nearly $900,000 to one of Dominic’s bogus businesses between October 2014 and January 2020, the indictment alleged. Dominic’s girlfriend, who died in January 2020, was the only person formally associated with the business.

The following month, a second company was formed, according to the indictment. The feds alleged that Dominic had the sweepstakes companies pay his business more than $500,000 in 2020 and 2021 in order “to conceal and avoid reporting his income to the Internal Revenue Service.” The company’s sole shareholder, identified only as “Individual B,” became Dominic’s girlfriend sometime before September 2024

Dominic did work for the sweepstakes companies, but his bogus businesses didn’t, prosecutors previously said. They said he “used nominees to receive income on his behalf” from the sweepstakes companies and directed them to enter into an agreement designed to conceal his income.

But Dominic only admitted to assisting in or advising the preparation of a “false and fraudulent” tax return for one of the companies in 2021, court records show. The return failed to name him as an owner of the company.

On Friday, prosecutors said Dominic doesn’t owe any money to the IRS.