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In 1991, George H. W. Bush had a record-setting presidential approval rating of 89%. His quick and decisive rout of Saddam Hussein’s forces in Kuwait had made him a White House war hero. It was a matter of uniform opinion that he was unbeatable for re-election. Consequently, some of the largest Democratic names such as Mario Cuomo, Ted Kennedy and even Al Gore (whose decision was also complicated by the health of his son) opted to wait for next time. Enter Arkansas’ Bill Clinton, with an able assist from Ross Perot and a “read my lips” flip-flop by the elder Bush. Next time never arrived for that class of would-be candidates — although Gore, as vice-president came within a few hanging chads and sitting supreme court justices of success.

While we’re playing What If, consider this alternative universe. In 2006, Bob Rae narrowly missed a shot at the final ballot of the Liberal leadership convention at least partially because he had no Parliamentary seat after opting to not run in the previous general election. We can’t know for sure but I’d bet a roomful-of-regrets that had he accepted Paul Martin’s invitation to run for Parliament in 2005, Rae would have been elected party leader in 2006. It seems downright cruel to imagine but with his political skills and Harper’s fragile minority government, who knows how history might have unfolded. Rae’s decision in 2005 might well have cost him his best shot at 24 Sussex.

The same lesson in reverse can be taken from more recent times. In 2013, Justin Trudeau became Liberal leader even as his party languished at its lowest historical point. Many observers thought his timing was rash. Better, they argued, to leave the hard work of rebuilding to someone else and then eventually take the party that last mile back into government. Trudeau, whose own father had resurrected the Liberals from a deep funk in 1968, thought better. He understood that if the party was going to be reinvigorated, it would require his vitality to get the job done. Recognizing his opportunity, Trudeau took action. And today he towers over the Canadian political landscape as a majority prime minister.