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):
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