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Vrdolyak pleads guilty to tax evasion and again finds his fate in hands of judge

Former Chicago Ald. Edward Vrdolyak walks with his lawyers out of the Dirksen Federal Courthouse after pleading guilty to federal tax evasion charges, Thursday morning, March 7, 2019. | Ashlee Rezin/Sun-TimesFormer Chicago Ald. Edward Vrdolyak walks with his lawyers out of the Dirksen Federal Courthouse after pleading guilty to a federal tax evasion charge, Thursday morning, March 7, 2019. | Ashlee Rezin/Sun-Times

Former Chicago Ald. Edward Vrdolyak walks with his lawyers out of the Dirksen Federal Courthouse after pleading guilty to a federal tax evasion charge, Thursday morning, March 7, 2019. | Ashlee Rezin/Sun-Times

Ten years ago, former Ald. Edward Vrdolyak caught a huge break, or so it seemed, and earned the nickname “Fast Eddie” all over again.

Facing serious prison time after pleading guilty to fraud, Vrdolyak managed to stroll out of the Dirksen Federal Courthouse in 2009 with a sentence of probation. The next day, his smiling face appeared on the front page of the Chicago Sun-Times.

The headline: “Fast Eddie Walks.”

That sentence didn’t stick, and Vrdolyak served 10 months behind bars. But on Thursday, Vrdolyak found himself back in a familiar situation, pleading guilty to tax evasion in front of U.S. District Judge Robert Dow. Afterward, Dow set a July 23 sentencing date, conjuring memories of the uproar 10 years ago.

Clearly, Vrdolyak and his lawyers haven’t forgotten about it. They mentioned it in a court filing earlier this year, insisting prosecutors were “irked” by that sentence. They went so far as to say the result of that case was “likely part of the reason” Vrdolyak found himself under indictment again.

Regardless, the former powerhouse 10th Ward alderman again finds his fate is in the hands of a federal judge. He faces a maximum of five years in prison. However, Assistant U.S. Attorney Amarjeet Bhachu told the judge a more likely sentence would be 24 to 30 months. In 2009, the feds were aiming for 41.

Back then, Vrdolyak got caught pulling a scam with corrupt influence peddler Stuart Levine that involved a non-profit medical school’s real estate deal. This time, the backstory is Illinois’ big-time settlement with tobacco companies in the 1990s.

The feds say Vrdolyak managed to get a piece of the settlement, along with associate Daniel P. Soso, even though he “did no work on the tobacco lawsuit.”

It’s still not clear, even after Vrdolyak’s plea, how much money Vrdolyak put in his pockets. The feds have only said Vrdolyak and Soso “received in excess of $10 million in fees.” During his earlier prosecution, they also mentioned that Vrdolyak “has a guaranteed income stream of $260,000 per year . . . until 2023 from tobacco-related litigation.”

Regardless, Vrdolyak got pinched because he was in charge of delivering Soso’s share of the money. Soso wasn’t paying his taxes, though. And when the IRS told Vrdolyak to pay it whatever he owed Soso, he claimed he didn’t owe Soso a dime.

Then he paid Soso $170,242.

Vrdolyak defense attorney Michael Monico told reporters after Thursday’s plea hearing that, “this is a relatively simple tax case, that’s all it’s about. Nothing more.” Still, unanswered questions remain about the tobacco settlement, which could be resolved when it comes time for Dow to sentence Vrdolyak.

When that time comes, Vrdolyak’s lawyers will likely submit several character letters on Vrdolyak’s behalf. That’s what they did in 2009, and it played a key role in the decision by U.S. District Judge Milton Shadur to give Vrdolyak probation.

The judge described an “extraordinary volume and character” in the letters that, based on Vrdolyak’s reputation, he “would never have dreamed existed.”

Nevertheless, Shadur’s sentence prompted rare questions about the integrity of Chicago’s federal judiciary. Defense attorneys found themselves insisting to reporters he was “as fair a judge as there is.” Shadur died last year.

Prosecutors appealed Shadur’s decision. The appellate court eventually sided with the feds in a sharply critical ruling. Then, Vrdolyak wound up in front of U.S. District Judge Matthew Kennelly late in 2010. Kennelly gave Vrdolyak his new, 10-month sentence.

After that hearing, Vrdolyak faced a blunt question from a reporter.

Does he still deserve the nickname “Fast Eddie?”

Vrdolyak’s attorney told him not to answer.

Vrdolyak just responded with a glare.