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Kevin O’Leary’s Celebrity Jeopardy! Loss As Seen Through the Eyes of a Massive K-Money Fan

Canada's greatest capitalist fought the socialist Jeopardy! regime and won.
Mack Lamoureux
Toronto, CA
May 13, 2015, 10:11pm

Last night, Canada's greatest capitalist took a break from being a straight-up baller to play a game of Celebrity Jeopardy! and show the world why he is rich and they are poor. He was up against a dumb jock and some pleb who was once in space.

This should have been a cakewalk for Mr. Wonderful but he was fucked by anti-capitalist forces on Jeopardy!

Kevin O'Leary, flanked by Aaron Rodgers and Mark Kelly, blew kisses to his adoring crowd when his name was announced. Everyone knew who was going to win so why shouldn't he ham it up a bit? K-money rarely gets the time to do this sort of thing. O'Leary knew the game was his to such an extent that he spelled his nickname wrong just to fuck with his opponents.


The double Ls in"Mr. Wonderfull" stand for "Ladies Love."

O'Leary, much like the bond market, decided to bide his time slowly in the first round while his opponents burned themselves out racking up points. It wasn't until the twelfth question that K-Money stopped counting the commas in his net worth and decided to play with the peasants. You could see his two competitors flinch when O'Leary flexed his mighty intellect. It was go time for K-money. The answer was "Covering barely 100 acres this is the smallest country in Europe." The idiot from space unsurprisingly answered the question wrong, and O'Leary chimed in to take his rightfully deserved money.

"What is Liechtenstein?" O'Leary answered, no doubt casually thinking about how 100 acres is barely enough room for a starter's estate.

"Nope," responded Alex Trebek as the buzzer sounded. "What is the Vatican?"

What the hell kind of trick question was that? How dare Jeopardy! make O'Leary's podium say -$400. This man is on Shark Tank. Hell, this man is the Shark Tank.

A few more questions went by and O'Leary again graciously bowed, answering no questions. I imagined him mining this moment of being in the red for his next motivational speech. You don't get to be on the Lang & O'Leary Exchange without knowing a thing or two about sucking up every available motivational speech dollar.

When the show went to break, the astronaut was at $1,200, the jock was at $1,000, and K-Money was at -$400. He was going to tell the tale of his victory like a comeback story.


Upon coming back from a thrilling series of corporate messages, it was time for a little chat with Trebek. O'Leary spoke honestly about hard work, sweat and everything capitalism has given him. He also spoke about Boston charity he was playing for. He wasn't even going to keep his money. No, he's giving it to a charity. Another lesson in generosity and properly implemented tax breaks. Unfortunately, there was little time for O'Leary to remind us how he makes the world a better place though—there was a Jeopardy game to dominate.

O'Leary came out storming out of the gate in the second round.

"This is the model of guitar that Jimi Hendrix was playing at Woodstock."

O'Leary answered, "What is a Fender Stratocaster?" It takes an icon to know one.

He was back on the board, baby! Space man and football boy might as well pack it in and call it a day. Just to keep it interesting, O'Leary decided to bow out once again, until his ears pick up a question about Frank Sinatra, another homeboy that got rich doing it his way. He, of course, got it right. With $1,200, K-money has the next pick.

"Let's go for $1,000 big ones Alex."

O'Leary took some time soaking in our adulation before he hit his buzzer and in that time the space asshole stole it. This was a dick move, that was O'Leary's question, and he was just pausing for dramatic effect. This is the reason that NASA isn't well funded anymore. You don't fuck with capitalists and still get to go to Mars, space cowboy.


It was time for another break and then it was Double Jeopardy. The Money Round. O'Leary was going to make that space asshole pay for what he did… with interest. They unveiled the categories and Shark Tank was one of them.

Cue the feeding frenzy.

"Of course, we're going to start at Shark Tank," O'Leary said. Cutthroat. Business-like.

And of course K-Money got the question right and even dragged out his answer, "What is blood?" so that his opponents could feel his word daggers slip between their ribs. This was going to be The Red Wedding of Celebrity Jeopardy!, mental cuts from all sides as O'Leary whispered in his opponents' ears: "An O'Leary always pays his debts, starting with the one with the highest interest rate."

But then Jeopardy!'s socialist leanings began to show.

The conspiracy should have been obvious from the get-go. The question was something stupid about fish and chips—common people food. European food. Socialist food. How was O'Leary supposed to know that? The man may have been born a Canadian, but he's the most red-blooded, beef-eating American alive.

The questions were so rigged that football boy next to O'Leary started to win. You could see O'Leary smirking at football boy, who must have felt right at home among these stupid questions. K-Money's significantly dumber opponents started to build a lead. O'Leary, like the kind of man who gives business advice daily, decided to fight back with his own answers. Let the market decide what was right. Nothing changed and he got the question wrong and lost $400. Why would a businessman need to know about physics? Why do you need Newton's Laws when your bank account only goes up?


K-money jumped in again, losing an insignificant $1,600. You could almost see the gleam in Trebek's eye. Trebek. Born in Sudbury. Home of the Big Nickel. Home of miners and small dreams. His blue collar is apparent, no matter how expensive that suit is.

But K-money isn't a quitter; adversary, that old friend,can't keep him down and he fights on against the obviously rigged system. He answers another. He lands at -$2,400.

They asked our hero a question about Springsteen. What would he know about Springsteen? That's the music of losers, high school baseball players who don't make the show, men who join the union instead of crushing it, tramps who drive instead of fly. And soon enough he's back at -$2,800.

With that, O'Leary decided to stop answering, every non-gambler knows when to fold 'em. It was a right call. Soon it would be time for final Jeopardy! With O'Leary at -$2,800, Trebek rightfully gave K-Money a grand as a detente. The fucking insult of giving a man of means charity. It sickened me.

The final question was about business, a subject O'Leary owns like a vucana wool housecoat. This game was his.

O'Leary was asked about two men sitting on motorcycles. He took to the air and answered the "Wright Brothers." Alas, they were Harley and Davidson. Grounded men. Springsteen men. Sudbury men. Socialist men.

O'Leary bet everything, not knowing the game was more Marxism than market. He ended with a final tally of -$3,800 and football boy won.

His winnings were going to charity and now he had none to give. Like a true fucking Capitalist. Well played, O'Leary. Well played.

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