Robert “Bobby” Dominic, a Chicago businessman linked to organized crime, faces charges of tax evasion. Federal authorities allege he had a concealed interest in a sweepstakes gaming company operated by his associate, James Weiss, who is now imprisoned. Dominic’s indictment was revealed in U.S. District Court, accusing him of evading taxes and failing to file tax returns over several years.
The charges state Dominic received payments through a fictitious entity owned by his deceased girlfriend and later through another company. This arrangement allegedly funneled over $1.2 million to Dominic, unreported to tax authorities. The indictment suggests a scheme to avoid taxes on earnings from these gaming companies.
Legal Maneuvers and Marriage Plot
Dominic’s involvement in the case has deep roots. Reports indicate his alleged activities were supported through strategic marriages. Individual B, another woman mentioned in the investigation, reportedly married Dominic to evade testifying before a grand jury.
Records show Dominic’s wife opened Promotional Consulting Inc., sharing an address with Richard’s Bar, a location tied to Dominic. Legal representative Edward Eberspacher declined to comment on these developments. The indictment doesn’t specify the total tax liability but outlines significant undisclosed income.
Broader Investigation and Mob Connections
This indictment stems from a larger probe into illegal gaming operations that brought other prominent individuals like ex-state Rep. Luis Arroyo and James Weiss under scrutiny. Previously, Weiss was reported to have connections with mob enforcer Frank “The German” Schweihs, linking him to Dominic.
Prosecutors label Dominic’s described gangster lifestyle as fitting. Undercover recordings suggest his collaboration with Weiss in gaming machine ventures, contradicting Weiss’ claim of being a law-abiding citizen.
Complex Web of Financial Entities
The investigation uncovered a complex network of businesses tied to Dominic and Weiss. James Weiss’ now-deceased girlfriend had financial ties to his gambling operations. Documents show connections with former police officer John Adreani and unsettled accusations involving illegal activities.
These entities were allegedly entangled with known mob activities, including a lunch meeting at La Scarola triggering an FBI sting operation. Dominic reportedly played a key role in settling disputes involving these circles.
Dominic’s affiliations with recognized mob figures underscore the entrenched criminal influence in these operations. The charges, part of a broader anti-corruption effort, aim to dismantle these longstanding networks.
James Weiss received a prison sentence related to bribery and fraud for his involvement in manipulating state gambling legislation. His brother, Joseph Weiss, faced charges for misleading investigators about mob connections. Legal consequences continue as Dominic’s legal battle unfolds.

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