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Unfortunately, the Canadian businessman did rather poorly. O’Leary, who misspelled his own nickname on the podium as “Mr. Wonderfull,” was playing for a Boston charity that encourages young people to go into medicine, but he proved no match for Rodgers and Kelly. He ended the first round barely keeping up with his celebrity competitors thanks to a couple musical clues, but by the end of the second round he was -$2800 in the hole after a disastrous response to a Bruce Springsteen clue.

Already down by $800, O’Leary was eager to get back in the game when host Alex Trebek asked for the city in the Springsteen lyrics “Oh brother are you gonna leave me wasting away on the streets of ___.”

O’Leary’s response: “What is New Jersey.”

Yikes.

Due to the relaxed rules in the celebrity tournament, O’Leary was allowed to play in the Final Jeopardy! round with $1,000, and given that the category was “Business,” one would think O’Leary might still have been able to save some of his dignity. Alas, the famous businessman still didn’t have the right response to the last clue of the evening.

The clue — “These two American businessmen are seen here in early 20th century photos” — was accompanied by images of two men in old-timey motorcycles with sidecars. O’Leary guessed that the two men were the Wright brothers, famous for building the first successful airplane. Alas, the correct response was “Who are Harley and Davidson?”

None of the contestants got the correct response, but Rodgers ended the night as winner with $8,339, Kelly left with $4,300 and Canada’s own Kevin O’Leary had the honour of walking away with a total of $0.

For more on “local capitalism mascot” Kevin O’Leary’s performance on Celebrity Jeopardy!, please see Torontoist’s minute-by-minute recap of the episode.