What Would Outfit Boss Paul Ricca Say About Pritzker the Whale?
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.
-30-
The Chicago Outfit’s St. Valentine Massacre
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.
Merchandise Now Available: If you’re looking for a gift for that hard-to-buy for special someone who has everything, just click on the link to the johnkassnews.com store.
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Comments 55
Illinois likes their buffoons, as gangsters, Cardinals, like Blase it Forward Cupich, activist priests like Blonde Jesus Pfleger, politicians like Dick Durbin and Governors like Jolly Blimp “Hit Me” Pritzker. The lesser clowns of the media (WGN et al) bask in their glow and voters lap it up.
Serious people have slower appetites for buffoons, clowns and the creeps they serve.
So true Mr. Hickey.
I wonder what the odds are Dabrowski vs. Jabba ?
The gambling interests in Illinois are too smart to just hand JB a bag with $1.4 million in it so that casino-friendly legislation is greased through the ILGA. Much easier to invite him to Vegas and sit him at a blackjack table with a “friendly” dealer.
Bribe? What bribe? He’s just a lucky card player.
Lou Berardi : Pritzker’s absurd accusations of ICE officers running amuck don’t match video that Americans are watching of violent thugs attacking law enforcement . He’s created a fantasy world where he’s the new César Chávez, willing to go to jail for farm workers. He expects Americans to ignore the human traffickers and drug smugglers at the Broadview center. This casino scam is just more of the same. Pritzker is another Bernie Madoff, always scheming to trick the voters into new tax hikes. . . . https://youtu.be/HMIyDf3gBoY
“Right on the money”, exactly
Time to break out the forensic accountants. What are the odds that someone who reported $1.4 millions in winnings, after reducing the winnings by the gambling losses in the same tax year only had gambling winnings on one tax return? Probably the same odds as the wife of a former governor from Arkansas made over $100,000 trading cattle futures and never did that before or after either. Neither story passes the smell test. Oh, what a tangled web we weave when first we practice to deceive!
Michael, you are so right, especially the $100K on cattle futures that she learned from reading the WSJ.
So true MR. Salazar.
“But once we’ve practiced for a while, how greatly we improve our style”.
Source unknown
Thanks John and good morning.
Because this is Illinois and he is the current governor, I too have doubts about his gaming luck.
How many Illinois governors have been sent to prison in the last 50 years? Four? Will Pritzker be number Five?
Maybe. But we will need a larger governor prison wing.
(D-how you doin?) LOL! My first laugh of the day, and thank you, John.
Leave the gun, take the cannoli!
A great part of many. That line wasn’t in the script.
Yianni,
I said it as soon as this story broke, on Fox News. Winnings my kolo! Was payback for backing casinos in Illinois. Not as overt as a bag full of cash, like in the old days, but a bribe nonetheless. Of course mainstream media won’t touch it with a ten foot pole, but those of us with a few gray hairs have seen this story before, and know the ending may not be so pretty. Stay tuned….this is only the first chapter…..
A vet reporter of Chicago crime with strong instincts and a sense of humor can recognize Pritzker’s $1.4 million “good luck” episode as a tale straight out of a Mario Puzo novel. (Read Puzo’s great, less-famous work “Fools Die” and you’ll enjoy a colorful parade of Pritzker-esque characters.) Of course, it was noted only by Kass because only an expert *former* Chicago journo has that brain and humor.
The biggest whales are stranger creatures than they might appear. They throw their enormous weight around and see every fish as dinner . . . or a vote. And when they swim to the waters of casinos, they know that special meals await them. On the house.
My first thought was that he could now afford to reinstall those toilets! Why do people vote for these jackasses?
Da fix was in —. And I thought the quote was “How YA Doin” ?
Gov Toilets — yet another example of how he and Durbin and Preckwinkle and Johnson look at their constituents as CHUMBALONES ! 1M400k playing cards. Talk about a friendly table. Any witnesses or was this a miraculous back room game. Boy have I got a bridge (over troubled waters) to peddle to you.
Thanks for being our Diogenes, John.
If he had played his hand as skillfully on the (wiretapped) Blago shakedown call, he might instead be soon inheriting senior Senator status here.
I like that you brought in Paul Ricca. A good example of a man of respect as a foil to buffoon JB.
Ricca would not boast about winning even $10M at blackjack. But I have ask myself what moron would, as a governor, boast that he went to Las Vegas Nevada and gambled? Really? Did he take in the shows? While the wife was shopping at Ceasars did he do something naughty-wink wink? Pritzker a Whale, more like a blow hole.
Great, now we got columns praising mobsters. I went to seminary, I learned Greek, Latin, Polish and Russian languages. But I didn’t turn to crime or kill anyone.
Really?
The only crime I can determine Tom that you continue to commit is issuing your buffonish and nincompoopish comments on a regular basis, and you are killing me with your retarded lack of wit. .
I will take the Charlie Kirk approach and tell you that you are entitled to your opinion, even if it’s wrong.
Thanks for this eye-opening Sunday column John. After retiring to drab and dismal Oregon ( where my family lives) I began flying to Las Vegas several times a year to enjoy sunny skies at luxury hotels & resorts that offer mid-week discounts. The Las Vegas culture is selfies everywhere, including casinos. Everyone takes photos of every sight, to make the folks back home jealous. I have to wonder how Hippo-man avoided those prying eyes while raking in all that loot. He’s been on national TV nonstop since he turned Illinois into the abortion capital of America in 2019. Las Vegas has powerful unions; and Hyatt Corp angered many rank-and-file hospitality workers in recent years. They know who JB Pritzker is. There’s no way he could sneak around a casino floor without someone noticing. Arrogant Pritzker is like the Hollywood Democrats who think they’re much smarter than working class taxpayers. George Clooney had upscale fantasies of private poker rooms with goons & bouncers to keep out his fans. But Nevada law requires every gambling area to be open to the public, no privacy screens or walls allowed. Every table is open to the tourists, sightseers and celebrity-watchers. Clooney’s casbah dream was dead in the water . . https://lasvegassun.com/news/2005/aug/29/clooney-joins-cast-of-investors-in-lv-project/
Tom, all great points.
So he reports $1.4 million in gambling winnings last year but previously released tax returns have not shown any gambling income. Seems kinda odd to me. Wonder if the IRS would be interested in this.
Humphrey Bogart : How can you close me up? On what grounds?
Claude Rains : I’m shocked! Shocked to find that gambling is going on in here.
. . . . https://youtu.be/HMIyDf3gBoY
Some inherited money can be used productively or in Fat Ass’ case, evil. For the life of me, I can’t figure out how his dad was as successful as he was, and only have one kid who isn’t screwed up. Two trans, Penny gave us Barry and is now destroying Harvard, and, of course this Bozo who’s never earned an honest dime in his worthless, corrupt, demonic life.
If Pritzker won the money as he claims, there would be a casino receipt and a tax declaration form stating state tax (Nevada) and federal.
LET’S SEE THEM.
And shop local?
Pritzker hates his own state so much that he has to go to Nevada to gamble? How many casinos are there in Illinois? Illinois is home to 17 casinos, approximately 9,000 licensed video gaming locations, and 14 active, approved sportsbooks.
Vacation? When you’re governor of Illinois, every day is a vacation.
“I’m not always a rat. Sometimes it just comes out.” Brad Marchand
Pritzker WILL be #5.
There are cameras recording everything in the casinos, where is the curious press?
I wonder how much he tipped the dealer. JB sure had an “unexpected” run of good luck.
John Kass- There’s a lot to disagree with in your column today- your subtle, implied admiration for a ruthless, lowlife criminal (Ricca), your clueless understanding of what’s behind the nationwide No- King’s protests (I attended both), and your tiresome “can’t let it go” animosity toward the Chicago Tribune.
Also, your characterization of Al Capone kept reminding me of Trump. 🙂
Bobby, go listen to NPR and leave John and the rest of us alone.
Thanks for your negative input. Did someone put glass in your cereal this morning! What was your favorite moments of sleepy Joe Biden’s presidency? Afghanistan withdrawal, Covid lock downs, Walking aimlessly on stage or into the wood, or falling out of the presidential race for Barack’s choice could run for your old spot. I could cite a lot more stumble bum moments but maybe you have another favorite.
Bob, were you one of those ancient grey-haired pony-tailed leftover hippies at the No-Kings scrum, perhaps one of those furrie fandoms or inflatable clowns, or tranny drag queens?
Bob:
What I get from your reply is that you went to a “See; we can protest without violence” protest.
John has a right to write about a former employer in any way he sees fit with animous or not.
I hate a former boss whom I wished a life time of eating from dumpsters somewhere in the middle of Ohio.
I am more cheerful when I think about all of the shitty people that I grew up with who-try as they might-had little to no effect on who I became as a person.
You know; you could be buying baseball cards with the money you are spending on subscriptions.
Hi Bob-Feeesa Etho!
Well Bob I disagree with much of what you wrote, but agree on one point you make. It seems incongruous – in fact unseemly – that John on one hand (rightly) criticizes Guv. Pritzker and Mayor Johnson for ignoring the rampant street crime in Chicago and then – at the same time – appears to glorify (or at least admire) a ruthless cold blooded mob king pin. This is a quote from the NY Times Oct 12 , 1972 obituary of Paul Ricca: “A Senate crime investigating subcommittee named Ricca the country’s “most important criminal” in 1958.”
Bruce- Yes, it was John’s apparent admiration for a piece of scum, murderous, mobster that I found particularly offensive.
A monster like Ricca does not deserve even the slightest shred of respect, especially from a journalist that seemingly considers himself so righteous.
Agreed. Don’t think Kass should write a book about him.
Keep disagreeing with everything Kass reports. Keep attending rallies with dimwits protesting on the side of those campaigning to be the new global kings: neo-Marxists and Islamists. Keep believing that what the Tribune, NPR, and remaining legacy media are feeding you is truth, warped as it is. You and Rudd provide sad comic relief here.
David, amen!
Mr. Bittinger- I don’t disagree with everything Kass writes but rather a large proportion of it, and that proportion seems to increase by the column. Also disagree with your groupie like approval of virtually every word.
Pog mo thoin
I had to look that up.
As usual, John nails it right on the head. I was also wondering if the casino Jabba the Pritzker was playing at has any pending legislation with the state. Was Jabba comped anything from a business entity waiting for a decision from the state? How much was the comp? Should it be reported as a campaign or lobbying “donation”? Funny how no Chicago “reporter ” thought to ask such obvious questions and it took Kasso to bring this up. You note I put the word reporter in quotes, like I was using the word as a joke . In the world of Chicago newspapers, it is…
What, JB the Son of Flubber has to go all the way to Las Vegas to gamble? Couldn’t he have just gone to the big new casino a couple of miles down the road from where I live? Especially since his and the Democrat supermajority’s idea of economic development for Illinois seems to be putting casinos, marijuana dispensaries, abortion mills, etc., on every corner. Why not put your money where your mouth is?
Every week the wheels just keep flying off – the Democrat. I was at No Kings rally in Evanston trying to get signatures for Ted – I lost count, but 10 is a good number – of people who recommended that I just leave Illinois. Not going to happen, we will change Illinois.
There is just no comparison – Dabrowksi vs Pritzker
I for one am thankful, very thankful, that the Outfit, Mafia, Cosa Nostra, Mob, whatever you want to call it, is a shadow of its former self. And despite its current and past problems, we must give credit to the FBI.
Paul Ricca was a thug, plain and simple. Didn’t believe in coincidences? Of course not, thugs never do, one the many ways they justify their hideous actions.
I agree 100%. Despite my misgivings regarding the FBI and such, I am under no fantastical delusions – as Kass seems to be – regarding the evil destruction wrought upon our nation by THE mob. It is disgusting that John sees a need to glorify such animals. I for one am under no delusion that I as a law abiding lone citizen would have had any chance of winning a “disagreement” if the mob came a calling. So yeah. Kudos to the FBI and RICO and the NYPD and the whole organized effort to make Mr. Ricca and his kind rare and endangered.
I don’t know the possible content of the book Kass is considering writing, but let’s just say this wasn’t his best column.
Lot of folks do not want to know the truth. They are out in space somewhere and have no clue whom they elect to represent them. Money talks. Sick of gossip and people that claim to be good people.