By John Kass

Wednesday Dec. 10, 2025

I’ve spent my life covering Chicago politics and Chicago political corruption.

So, I guess you could say that I’ve seen some things:

Many years ago, when I was first starting out in the newspapering business, the vaunted Chicago press corps—the corporate legacy media–was bowing and sniveling before a black “reform” mayor (not named Johnson) for fear of being branded as racists. This was just as the mayor’s top aide wearing a bad wig, collected rent in a city limousine from impoverished women living in his slum buildings full of rats.

Or later, when Chicago politicians were terrified into silence when Bill Hanhardt, the Chicago mob’s top jewel thief—who was insulated for years because he was also Chief of Detectives for the CPD as Hollywood made TV shows about him—was finally indicted for running the Outfit’s national jewel theft crew. As he was being sentenced in federal court he lifted a glass to me in a toast.

I don’t think I can print what was on his mind. And I don’t worry about the silence of the lambs. It was the silence of the politicians that screamed out a warning, from the mayor on down when the feds dropped the case of the Outfit’s top cop.

Chicago has always been a corrupt town, perhaps worse than Mogadishu Minnesota. Same media and Democrats frightened by the slightest suggestion they might be  blasted as racists by black demogoguges.

But what happened to a 97-year-old Tuskegee Airman takes the grand prize.

You’ve heard of the airmen. They were a highly decorated group of soldiers in World War II, they were heroes, some were escorts, protecting our American bombers from enemy fighter planes and others carried out bomb raids.

One mistake was death for themselves and their friends.

But thanks to the great CWB Chicago—the website that is all about bringing people the news rather than worrying about politically correct social justice scores—we know about Cook County Judge Patricia Martin.

This is true.  Judge Martin’s story does come to us from the one place Chicagoans understand: the Department of Special Places in Hell.

Martin is the former judge convicted of swindling an elderly Tuskegee Airman, Mr. Wilkerson, of his life savings. He found out about it after Judge Martin—who had his power of attorney to look out for him and pay his nursing home bills—stole hundreds of thousands of dollars from him.

She blew it on bitcoin.

Mr. Wilkerson found out about it when the nursing home wasn’t receiving money to pay his bills.

Martin once served as presiding judge of the Child Protection Division and retired in 2020 with a big fat pension that she sweetened, I assume, with extra contributions.

My friend Jeanne Ives reports that Judge Martin’s pension was well over $200,000 a year. Like a thick rib-eye steak on the bone, full of fat and flavor.

Prosecutors initially accused Martin of stealing nearly $250,000 from then-95-year-old Mr. Oscar Wilkerson, a longtime friend whose finances she controlled under power of attorney. Wilkerson’s wife had been a relative of Judge Martin.  Using that authority, Martin closed some of Wilkerson’s bank accounts and withdrew more than $115,000, officials said. She used the money to buy crypto.

CWB reports that investigators said she continued making unauthorized transactions for crypto purchases and personal expenses through 2021 and most of 2022.

The thefts were uncovered after a senior living facility terminated Wilkerson’s residency because of unpaid bills. An attorney was brought in to examine his finances and filed a lawsuit against Martin in 2022.

She failed to respond, resulting in a default judgment of about $1.1 million, according to court filings.

Because Martin previously served as a Cook County judge, her case was assigned to McHenry County Judge Tiffany Davis. Martin plead guilty. Wilkerson died in 2023, one day before his 97th birthday. Martin was disbarred the same year.

But here’s the kicker, she didn’t spend any time in jail. Not one measly day. And she keeps that pension.

Wilkerson, who died in February 2023 at the age of at 96, had been the last known surviving member of the Tuskegee Airmen in the Chicago area. In 2007, he was among about 300 surviving members of the trailblazing all-Black aviation unit awarded the Congressional Gold Medal by President George W. Bush.

Martin has since been disbarred. As part of her probation, which runs through Dec. 3, 2029, she must report to the county’s Adult Probation Department, complete drug and alcohol evaluation and treatment, submit to random drug testing and comply with DNA indexing requirements. Also, she’s barred from leaving Illinois without court permission and cannot possess firearms or other weapons.

In Mr. Wilkerson’s obituary, the Chicago Sun-Times reported that he rode a Pullman sleeper car but, upon crossing the Mason-Dixon line, was told to move to a Blacks-only train car — an experience that, in an interview with Chicago’s Pritzker Military Museum & Library, called his “first real hard taste of segregation.”

Fulfilling a childhood dream to fly, he became a bomber pilot with the Tuskegee Airmen, the famed unit that helped pave the way for desegregation in the military.

After leaving the military and coming home to Chicago, he found his job options limited despite his training as a pilot.

“After the war, we were not able to go into commercial aviation,” Wilkerson told the military museum. “Blacks weren’t accepted at that time. I couldn’t fly commercially. So, I became a bus driver in Chicago.”

He also worked at radio stations in Chicago and Harvey.

But he never lost his love of flying, and he delighted in sharing that with kids.

What gets me is that this was an inside deal played by Judge Martin, an inside player.

How do I know? She served no time in prison. Not one minute behind bars. And the pension remains fat.

She was part of the judicial clique of boss Toni Preckwinkle, who is boss of the Cook County Democrats and the supreme judge picker.

And Boss Toni has kept her mouth shut through all of this.

She’s as silent as a lamb. But she’s no fool. She’s up for election on March 17. And she’s kept her lips zipped on this one.

Will she be held accountable by voters?

I don’t see it happening. The Chicago media won’t hold her to account. She’s emptied the Cook County Jail of violent repeat offenders because she doesn’t want black men in jail. And Chicago media hasn’t held her to account. You might think the media would focus on her, but Preckwinkle does the bidding of the Chicago media’s social justice warriors. She is on the hard left and so are they.

The violent monster Lawrence Reed–who poured gasoline on innocent Bethany Magee and lit her on fire–was a beneficiary of Preckwinkle’s race based de-carceration policy. And still, Preckwinkle is constantly rewarded for her racial justice.

I ask you again. Will Preckwinkle ever be held accountable?

I don’t think so. This is Chicago, and Boss Toni knows how to play things the Chicago Way

She’s not worried. The media and Gov. J.B. Pritzker protect her. There is no Illinois Republican Party to carry the fight to Boss Toni. She’s at peace, laughing at you.

What would happen to you if you stole $300,000 from boss Toni? You know what would happen. And you wouldn’t be singing a show tune in the shower.

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About the author: John Kass spent decades as a political writer and news columnist in Chicago working at a major metropolitan newspaper. He is co-host of The Chicago Way podcast. And he just loves his “No Chumbolone” hat, because johnkassnews.com is a “No Chumbolone” Zone where you can always get a cup of common sense.

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