A federal magistrate recommended Tuesday that James “Jimmy the Greek” Gerodemos, the alleged leader of an illegal Northwest Indiana gambling ring, be released on a $5 million unsecured bond while the case is pending. But federal prosecutors indicated they plan to file an appeal by early next week — effectively pausing any release for at least several days.
The move is a potential blow to federal prosecutors — who argued Gerodemos could potentially threaten or intimidate witnesses, or flee the country.
Beau Brindley, one of Gerodemos’ lawyers, hailed the decision after the hearing, saying prosecutors wanted to paint his client as a “crime boss, when he’s not.”
An 87-page indictment filed in April in the U.S. District Court in Hammond detailed the alleged gambling and extortion activity between January 2021 and April 2026, naming Gerodemos, 63, of Schererville, and Dean Gialamas, 61, of Naperville, as leaders of the Gerodemos Gambling Organization, which allegedly ran an illegal gambling ring out of two longtime Northwest Indiana restaurants, Gino’s Steakhouse in Merrillville and Paragon in Hobart. All 22 defendants pleaded not guilty to federal charges in May.
During the hearing, Assistant U.S. Attorney Philip Benson and Brindley sparred over whether Gerodemos’ alleged actions in the case was a “crime of violence” — to meet a legal standard for keeping him behind bars. Magistrate Andrew Rodovich ruled it was not.
Benson argued in court Gerodemos’ past actions could spell trouble if he were released — including a May 2024 “swatting” incident against a former tenant who had previously complained of harassment by Gerodemos in Chesterton over an outstanding gambling debt.
Gerodemos’ gambling organization had a “far” reach and “spanned decades,” Benson wrote in filings, which included “the corruption of high-ranking law enforcement officials.” When Gerodemos was arrested, police found “highly sensitive law enforcement documents” in his residence, Benson wrote.
Brindley countered in court that those documents were at least 25 years old and it wasn’t certain how Gerodemos got them.
If Gerodemos were to intimidate a witness, for example, the government would likely find out about it and slap him with more charges, Rodovich said in court.
In court filings, Benson argued again Gerodemos could potentially flee to Greece, noting his elderly father owned land there.
He included a news article on Konstantinos “Kosta” Diamantis, described in media reports as an ex-Connecticut “school construction official” who fled to Greece earlier this month before his federal sentencing for corruption.
Brindley said in court that Gerodemos was not a dual citizen, his assets were “frozen” and passport was seized. The lawyer said his recent trip to Greece, where he was photographed with Sidewalk Six fugitive Frank Kollintzas, was his first trip there in nearly 30 years.
“Being Greek is not a basis for pretrial detention,” Brindley wrote in court filings.
A status hearing is set for next June.
As a release condition, Gerodemos’ immediate relatives would have to sign off on his bond and surrender their passports.