Oct. 19, 2025

By John Kass

Illinois Gov. J.B. Pritzker had one of those weird grins on his face. Like a kid who’d just been caught stealing grandma’s blueberry pie after gorping down every bite and a half-gallon of vanilla ice cream to boot.

He was telling reporters that he won $1.4 million playing blackjack in Las Vegas in one day.

And that got me thinking of the late Chicago Outfit boss Paul “The Waiter” Riccca and gamblers. You might not call it the Outfit where you come from. But in Chicago, it has always been called the Outfit. And Ricca was the undisputed boss.

Ricca was ruthless. He did not believe in coincidence and he did not believe in luck.  He believed in planning. He was reserved and he fascinated me, unlike other Outfit bosses who were in large part merely a collection of ravenous appetites, brutal animals. Betty and I met his granddaughter at the Sicilian Summer Block Party, near Addison and Nordica this past summer. It was a brutally hot day. She was a gracious young woman and she appreciated the columns that I had written about him.

We sat in the shade of a tent provided by Josephs Finest Meats, had some lemon ice and talked. And I told her I had long thought of writing a book about Ricca. Why? Because he was not like the buffoon and braggart Al Capone as played by the equally buffoonish Robert DeNiro. Instead, Ricca was reserved, brilliant, a seminarian who studied languages. A strategist and a killer. He was no chumbolone like the politicians he bossed. He could call a politician up on the phone and tell him there was a horse farm out far to the Northwest that would make a great airport, and it was done, named after the son of Outfit lawyer Easy Eddie O’Hare.  More on Ricca later.

On Thursday Pritzker was standing before reporters, telling them how lucky he was to win that big pile of loot by playing cards.

“I was incredibly lucky,” Pritzker said on Thursday, responding to questions from reporters about his 2024 tax returns.

He said it all came from a single trip to Las Vegas last year with his wife, MK Pritzker, and some friends.

He didn’t say if those friends were Illinois politicians or Illinois casino investors. He didn’t say if it happened the kind of swanky private table where casinos entertain their coveted whales (millionaire gamblers). No reporters followed up with questions he wouldn’t like. The local news media has gone woke and is now going broke, and they don’t want to anger the billionaire fat man. They know they’ll need jobs some day.

If you think it all sounds like a wild story your banker would not believe, you’d be right.

Pritzker, an heir to the Hyatt Hotels fortune, did not say how much he had wagered per hand, but he did say he had “fun doing it.”

“Anybody who’s played cards in a casino knows that you often play for too long, and lose whatever it is that you won,” he said. “I was fortunate enough to have to leave before that happened.”

Rather clumsily and obviously he threw in a mention about organizing a card game for the Holocaust Museum, but all that does is raise more eyebrows.

A campaign spokesman said Pritzker would donate the money to charity.

No one in Illinois politics is rushing forward to congratulate Pritzker, including the members of the Illinois Gaming Board that he appoints, and not even noted Caribbean casino expert, former State Sen. Jimmy DeLeo (D-How You Doin?)

The leading Republican candidate for governor, fiscal watchdog Ted Dabrowski is also not amused. As Pritzker runs Illinois further into the ground, Dabrowski notes that the state should be in the top five in the country in economic and population growth and other categories. Public K-8 education under Pritzker prepares most Illinois schoolchildren for two main career paths: Prison or welfare or both

Illinois should be a top 5 state in this country – in economic growth, wage growth, population growth,  .

But we’re not. Under @GovPritzker, we’re a bottom five state in virtually every key metric.

This is a change election. Vote @TedforIllinois.#twill @ilgop pic.twitter.com/R1yfjrCnWR

— Ted Dabrowski (@ilpoliski) October 15, 2025

Pritzker and Chicago Mayor Brandon Johnson have been quite effective in screaming about President Trump to supply Democrat leftists with hate for their theatrical “No Kings Day” protests. And they supply these shiny objects to distract the Chicago media, so reporters won’t bother with difficult subjects like rampant street crime, lousy public education, or Illinoisians driven out by increasingly high property taxes to pay for leftist Democrat government programs.

And “No Kings Day”–or more accurately the Democrats Hate America Day– is merely performative theater to distract the chumbolones.

The weekend leftist rallies are reportedly organized and funded in part by George Soros and the Communist Party of America, so don’t bother seeking in-depth follow-up reports in the Soros-friendly Chicago Tribune.

And Pritzker playing poker and winning, while never telling us who he played with?

It all sounds rather precious, like body humor slapstick for idiots who are trapped in that hell.

I never heard the Outfit boss Paul Ricca laugh, but if he were alive to hear Pritzker’s story about luck he might have laughed mirthlessly. A quiet laugh, like a wolf while staring directly at the governor of Illinois.

And Pritzker the coward would leave a puddle on the floor.

No one in Illinois politics is rushing forward to congratulate him, not even the famous casino expert and former State Sen. Jimmy DeLeo (D-How You Doin?)

Paul Ricca, the boss of bosses of organized crime in America from the time he was sent to Chicago from the families in New York. There were no movies made about him. The movies instead liked Capone the loud buffoon.

Like I said Ricca was ruthless, a killer. He detested publicity and flew under the radar. Hollywood never made a movie about him. He was brilliant, educated in a seminary, and it is said he spoke several languages. Legend has it that when he was a young man his sister was violated. Ricca killed the man with a knife. He was sent to prison. Years later, he was released. And the next day the witness was dead, stabbed with the same knife.

From the time he came to Chicago to watch over Al Capone — the publicity seeking buffoon fronted off to the public and the press as the beclowned mob boss — and until he took his last breath, Ricca’s word was law. From New York to Los Angeles which includes Hollywood, Las Vegas, Kansas City, and naturally Chicago.

I’m told that  that one day Ricca was being driven along Cermak Road, named to honor a Chicago mayor who died suddenly of lead poisoning, when someone in the car began complaining about another gangster from the Chinatown crew.

The guy in Ricca’s car wanted the other gangster to die a slow painful death from cancer. Or that he should be killed outright.

“Stop. That’s a terrible thing for you to say, that he should get cancer,” Ricca said. “Or be murdered. And cancer? How could you say such a thing? You wish that kind of suffering on someone? That’s terrible.”

The other guy in the car was terrified, thinking he’d angered the boss. Ricca was silent for a moment, then asked.

“Do you really hate this man?”

Yes, Ricca was told.

“Then don’t wish him to have cancer. Don’t just kill him. Wish him to be a gambler,” the boss said. “It takes longer.”

And Paul Ricca smiled.

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About John Kass

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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