Kevin O’Leary Embarrasses Himself on Celebrity Jeopardy!: A Recap

Local capitalism mascot outperformed by an astronaut and a football player.

By David Hains

The lineup for the second episode of Celebrity Jeopardy! in 2015. Photo courtesy of Sony Television.

7:30 PM: This! Is! Celebrity Jeopardy! So says longtime announcer Johnny Gilbert as he introduces the contestants for the second episode of this year’s Celebrity Jeopardy!, where the questions are easier, the contestants are less awkward, and the money goes to charity.

There’s astronaut Mark Kelly, who is married to former Arizona congresswoman Gabrielle Giffords. He’s logged over 38 days in space. In the middle of contestants’ row is our hero Kevin, who is most famous for being capitalism’s Don Cherry. And to Kevin’s right is Green Bay Packers quarterback Aaron Rodgers, who has won a Super Bowl and twice been named the NFL’s most valuable player.

But do either Kelly or Rodgers play Mr. Moneybags on TV? I don’t think so.

7:32 PM: On the screen where contestants write their name, O’Leary writes “Kevin,” and below it includes his nickname. Except he spells it wrong, and writes “Mr. Wonderfull.” Is it possible Kevin O’Leary is not as smart as he says he is? We will find out by judging him in the only fair way possible—by how he performs in a televised trivia competition.

7:32 PM: On the first clue of the game, Kevin doesn’t buzz in. This must be part of his cunning strategy to lull the less worthy competitors into submission before showing his mettle. If there’s one thing Kevin O’Leary knows, it’s how to make money, as he will remind anyone who will listen.

7:34 PM: Still waiting it out without buzzing in, the sly dog. This is a good time to remind people that O’Leary might be better at self-promotion than actually making money, as reported in this 2012 Report on Business feature.

7:35 PM: O’Leary finally rings in! Asked what the smallest country in Europe is, he says it’s Liechtenstein, that lovable tax haven. It’s not, though—it’s Vatican City. Oops.

7:36 PM: We break for commercial, and O’Leary sits in last place at -$400. But hey, maybe this is worth celebrating? Maybe this will inspire O’Leary to pull up his bootstraps and match the Jeopardy! prowess of Aaron Rodgers? As O’Leary once argued, we should celebrate the big gap between the wealthy and poor for the motivation it provides the have-nots.

Photo bombing @kevinolearytv on the @Jeopardy set pic.twitter.com/uiOsfY8U9v

— Aaron Rodgers (@AaronRodgers12) May 12, 2015

7:39 PM: Alex is now interviewing the contestants, and here’s our man Kevin! He talks about the unparalleled beauty of capitalism, and how it creates liberty for those who pursue it, and adds that he’s playing for a medical charity in Boston.

7:41 PM: Kevin gets his first question right! He knows what kind of guitar Hendrix played at Woodstock, because he’s hip like that. Actually, O’Leary loves guitars and collects them, so it makes sense that this would be in his wheelhouse.

7:42 PM: Kevin gets another one right, and then tells Alex he wants the next clue in the category for “1000 big ones.” Oh Kevin, with your fancy biz talk! Tell us more about why you’re so successful and important. *puts hands over cheeks*

7:44 PM: At the end of the first round, Kevin is in third place with $1,200, and it’s sad to see how the mighty have fallen. It’s almost as sad as drinking some O’Leary Fine Wine in the middle of the day while watching His Wonderfulness offer celebrity commentary on an eTalk rerun.

7:47 PM: Maybe that first half was just the setup for the inevitable O’Leary comeback? Let’s find out. Kevin chooses the category “Shark Tank” to lead off Double Jeopardy!, and gets it correct. Things are finally turning up Kevin. The market works.

7:48 PM: Just as quickly, Kevin disappears again as Aaron Rodgers dominates Jeopardy! like the final two minutes of a close football game. This is a lovely way to make Kevin O’Leary silent.

7:50 PM: Kevin is in the negative again, running at a non-wonderful -$2,400. He’ll have to fight to meet his quarterly target of not embarrassing himself on television’s most respected quiz show.

7:51 PM: After getting a couple of questions correct to move to only $800 in the red, Kevin can get on the plus side of the ledger with the correct $2000 question in the category “Cities in Song”:

Alex: “Bruce Springsteen: ‘Oh brother are you going to leave me wasting away in the streets of’ this city.”

Kevin: “What is New Jersey?”

Not even “What is Atlantic City?” And certainly not the correct question, “What is Philadelphia?” Kevin O’Leary is $2,800 in the hole. If you’ve ever wanted to see the smarmy, all-knowing grin wiped from his face, this is a very fine moment.

7:54 PM: Double Jeopardy! is over, and Kevin finishes in the negative, with -$2,800. In normal Jeopardy!, O’Leary would suffer the indignity of not being worthy enough to compete in the final round. But this is Celebrity Jeopardy!, and so the normal rules do not apply; Kevin will receive $1,000 pity dollars so he can play with the smart kids. Even on a game show, he’s too big to fail.

7:56 PM: The category is business, which should be right up Kevin’s alley. The contestants are given two pictures of men on early facsimiles of motorcycles and asked to identify them, although the vehicles could be mistaken for cars.

As the player in last, Kevin shows his answer first. He responds, “Who are the Wright Brothers?”

The correct question—and it was a relatively tough one for Celebrity Jeopardy!—was “Who are Harley and Davidson?”

Kevin, that great believer in meritocracy and the idea that money is the best way to keep score in life, finishes with a score of $0, having bet all of his pity money. O’Leary’s performance isn’t quite Wolf Blitzer bad, but you have some sympathy for Ol’ Wolfie that you don’t for the self-described “Mr. Wonderful.”

The schadenfreude is delicious. O’Leary’s chosen charity still gets some money, Jeopardy! preserves its integrity, and, to give him his due, “Mr. Wonderfull” handles it all in good humour.

Oh, and Aaron Rodgers wins.