All of them are in their 70s, already convicted felons.
And there's a connection to the case of a famous stolen diamond that has never been recovered.
Joseph "Jerry" Scalise, Robert "Bobby" Pullia and Arthur "the Genius" Rachel were charged in 2010 with conspiring to rob a suburban bank, an armored bank truck and a Chicago residence. It's the home where deceased mob boss Angelo "the Hook" LaPietra lived and where family members still live today.
Scalise and Rachel are well known for their daring, day-time heist of the 45-carat Marlborough Diamond, stolen from a London jewelry store back in the 1980s. The pair served 10 years in a British penitentiary for the crime but the diamond was never recovered.
Wednesday, Scalise and Pullia entered guilty pleas to U.S. District Court Judge Harry Leinenweber and face roughly eight-and-a-half to nine-and-a-half years in jail.
Rachel is the only member of the group risking a trial. On Wednesday, he requested a bench trial that will begin Thursday morning.
Recently, the prosecutors intercepted a letter 74-year-old Joseph "Jerry" Scalise wrote to corrupt former Chicago Chief of Detectives William Hanhardt, where he essentially made a confession.
In Scalise's letter to Hanhardt, he wrote that "everyone in court looks at you as guilty and that defendants often forget they did do the crime. The only approach," Scalise wrote, "is to make something else the issue to trick the jury."
Former federal prosecutor T. Markus Funk initiated the case against the trio before moving on to private practice. Evidence federal agents collected in the case includes a stash of stolen guns and a modified econoline van that prosecutors claim, the men planned to use in their robberies.
"I think that van spoke volumes about what their intentions were," Funk said. "The fact that there were slots cut out basically to be used, we believe, to be used to shoot people who come up to the car, I mean that's a pretty terrifying thing."
Pullia's defense attorney passed along a message for his client.
"He's in good spirits and he wants everyone to know he is not cooperating," defense attorney Marc Martin said. "Cooperation is not a part of this plea agreement."
Scalise and Pullia remain under house arrest until they go into custody on Feb. 8. Sentencing is scheduled for May 10.