Feds want more than two years for man behind ‘massive’ gambling ring, say he tried to keep it going

Prosecutors say Vincent “Uncle Mick” DelGiudice was thwarted when Mettawa Mayor Casey Urlacher, brother of Chicago Bears great Brian Urlacher, was also charged and things got “hot.”

SHARE Feds want more than two years for man behind ‘massive’ gambling ring, say he tried to keep it going
Vincent DelGiudice walks out of the Dirksen Federal Courthouse, Wednesday morning, March 4, 2020.

Vincent DelGiudice walks out of the Dirksen Federal Courthouse in March 2020.

Ashlee Rezin/Sun-Times

Federal prosecutors want a judge to give a prison sentence of more than two years to a man who admitted running what the feds have called the largest gambling operation uncovered in the history of Chicago’s federal court. 

Prosecutors allege that Vincent “Uncle Mick” DelGiudice hoped to keep his operation running even after his February 2020 indictment — only to be thwarted when Mettawa Mayor Casey Urlacher, brother of Chicago Bears great Brian Urlacher, was also charged and things got “hot.”

“It’s all due to Urlacher,” read a message he apparently received days after the indictment.

But DelGiudice attorney Carolyn Gurland denied it, insisting in a memo to U.S. District Judge Virginia Kendall on Friday that evidence shows “the vast majority of gambling activity ceased” immediately after a raid of DelGiudice’s home in April 2019.

Gurland asked for two years of probation and six months of community confinement for DelGiudice.

DelGiudice pleaded guilty in February 2021 and admitted he ran the ring. The feds have called it “a massive, high stakes criminal” operation that also reached into California, Arizona and Kentucky and established a foothold at Illinois State University. They said it profited more than $8 million just in 2018. 

When the feds searched DelGiudice’s home in April 2019, they said they found more than $1 million in cash, two cash-counting machines, gold bars, silver and jewelry.

Also charged in the case was Nicholas Stella, a Chicago police officer who would be sentenced to 15 months in prison. A former Melrose Park police officer, John Amabile, would also be charged in a related prosecution and sentenced to six months in home detention.

But many of those charged along with DelGiudice have avoided prison time. Casey Urlacher was pardoned in January 2021 by Donald Trump in the final hours of Trump’s presidency.

Prosecutors are also seeking significant forfeiture from DelGiudice, including a $3.5 million money judgment. Gurland argued in a separate court brief that prosecutors initially sought much more — including a money judgment of $8 million — but reduced its request at the end of a days-long hearing last October. 

She called that “powerful evidence” that prosecutors failed to prove their forfeiture case. On Friday, she noted prosecutors did not seek forfeiture from any of the other charged defendants. DelGiudice has agreed to a judgment of $1.2 million, she wrote.

Assistant U.S. Attorney Terry Kinney wrote Friday that, days after DelGiudice confessed to the FBI in April 2019, he reached out to several of his gambling agents and asked them to keep gambling with him.

Agent Keith Benson, who still faces pending charges in the case, agreed to cooperate with the feds, according to Kinney. Benson allegedly told the FBI that, four days after the search of DelGiudice’s house, DelGiudice sent him a link to an app they could use to secretly communicate.

Benson also allegedly told the FBI that DelGiudice began using a new website to run his operation. Then, from April 2019 until February 2020, Kinney wrote, DelGiudice sent Benson images of handwritten ledger sheets through the app that documented gambling figures owed by Benson or his gamblers. 

However, after the indictment in February 2020, DelGiudice and Benson began having trouble with the website, and DelGiudice allegedly texted Benson that he planned to call the manager.

A few days later, DelGiudice allegedly forwarded a response from the website that read in part, “clients are leaving and others refusing to send payments. … It’s all due to Urlacher … We probably won’t survive this anyways.” DelGiudice allegedly responded to that note by asking for the names of the website’s attorneys at the request of his own.

“Continuing to run a gambling operation after the FBI conducts a raid on your house, and trying to continue post indictment only to be shut down by a third party because things got too ‘hot’ scarcely demonstrates ‘… genuine remorse or conscience,’” Kinney wrote.

Gurland wrote in her Friday memo that Benson denied in a February 2021 interview knowing about an ongoing gambling business by DelGiudice. She also insisted that DelGiudice involved his criminal defense counsel in the matter with the website and shut talks down voluntarily.

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