Remembering When Kevin O'Leary Totally Tanked on Jeopardy!

This article was originally published August 11, 2021.

If you've watched even a little bit of Shark Tank — hell, if you've merely seen a promo for Shark Tank — you're probably familiar with Kevin O'Leary. The Canadian businessman and sometime politician was the early face of the program where multi-millionaire investors get pitched new product or service ideas and then compete to invest in them.

Adopting a knowingly abrasive "Mr. Wonderful" personality, O'Leary helped to brand the show as a place where wealthy people not only found new investments but also showed off their personalities (over the years the show has picked up the likes of Mark Cuban and Bethenny Frankel as panelists). O'Leary's life as a media personality expands this week with the premiere of Money Court, a new CNBC show where O'Leary leads a three-person panel that will arbitrate financial disputes, People's Court-style.

O'Leary's position as adjudicator-in-chief on Money Court stems from the same idea that makes someone whose approval must be courted on Shark Tank: the idea that his ability to make money makes him wise. This isn't a new or radical notion. The idea that rich people must know things that the rest of us mere mortals don't is the kind of fallacy that gets certain people elected president.

Which is why it's so satisfying to see those kinds of assumptions get knocked down in public, as they were in a 2015 celebrity episode of Jeopardy, when O'Leary went up against NFL quarterback Aaron Rodgers and astronaut Mark Kelly. While Rodgers did so well on the episode that he would eventually be invited back as one of the show's many temporary guests hosts in the wake of Alex Trebek's death, O'Leary did just about as poorly as any celebrity has ever done on the show. When it comes to Jeopardy schadenfreude, only Wolf Blitzer's infamous fail compares, but it's much more fun to revel in O'Leary's ineptitude.

While O'Leary's Jeopardy faceplant is unfortunately not available to stream in its entirety, Canadian progressive news site PressProgress put together a kind of anti-highlight reel back in 2017 when O'Leary was running to lead the the country's Conservative Party (he dropped out a month before the election):

There's some debate over whether O'Leary managed to get something even before a single question was asked, with some viewers contending he mispelled his own moniker on his podium, although O'Leary's defenders say what looked to some like an extra "L" in "Wonderful" was in fact an exclamation point.

His first incorrect answer involved tiny countries in Europe, with O'Leary incorrectly guessing "Liechtenstein" when the answer was "Vatican City." By the time the show broke for its first commercial, O'Leary was already at negative $400, and while he was able to crawl out of the hole to $1200 by the end of the Jeopardy round, he held the unfortunate distinction of having to go first in Double Jeopardy.

Double Jeopardy is really where the wheels fell off the wagon for Mr. Wonderful(l), as he offered repeated wrong answers, including one fairly embarrassing moment where he was asked to provide the name of the city Bruce Springsteen was singing about with the lyrics "you're gonna see me wasting away in the streets of [this city]." Now, even if you don't know the song, or can't guess from the context that Springsteen had a well-known, Oscar-winning song called "Streets of Philadelphia," you'd know that Alex was asking for the name of a city, which made O'Leary's guess of "What is New Jersey" truly a blunder. Just don't buzz in, my guy!

In the cruelest turn of the knife, the Double Jeopardy round ended with O'Leary massively in the red at negative $2800. In a regulation game of Jeopardy, that would mean the contestant was ineligible to compete in Final Jeopardy (since they'd have nothing to wager). But since this was Celebrity Jeopardy and charities were at stake, the show floated O'Leary's total up to $1000 so he could play with the other boys. One has to imagine the indignity felt by a famously conservative businessman and sometime politician to have to be given a handout due to his own ineptitude.

But if you're worried that O'Leary's pity money was able to let him finish ahead of his more trivia-adept rivals, fear not. He misidentified the motorcycle pioneers Harley and Davidson as the Wright brothers, knocking his total back down to zero.

This universe is not always a fair place. The rich and pompous often go far while the smart and humble are stymied. But sometimes the universe plays equalizer, and sometimes Celebrity Jeopardy acts as its instrument. So when you watch Money Court this week and you see Kevin O'Leary rule with assumed wisdom, just remember that this is a guy who thinks New Jersey is a city. It'll improve your day.

Joe Reid is the senior writer at Primetimer and co-host of the This Had Oscar Buzz podcast. His work has appeared in Decider, NPR, HuffPost, The Atlantic, Slate, Polygon, Vanity Fair, Vulture, The A.V. Club and more.