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Brad Wall likes to tell an apocryphal story about a canoe race being led by a man from Saskatchewan.

As he's nearing the finish line, the man looks around to see where his fellow competitors are. Noticing they are lagging far behind, he slows down, giving them a chance to catch up so they can all cross the finish line together. For the Saskatchewan Premier, it is the quintessential story about his province, which has long been known for the kind, generous people who live there: prairie folks not known for their competitive streak.

As he prepares to leave office after 18 years as an MLA from Swift Current, 14 years as leader of the Saskatchewan Party and a decade as Premier, Mr. Wall looks back on his career and says with some pride that if nothing else, he hopes his tenure made the people of his province understand that "it's okay to win, as long as you're gracious about it."

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There is little question that the popular premier gave his province a profile on the national stage it hadn't had in some time – if ever. His people liked it. If Mr. Wall was a reflection of all that Saskatchewan represented, then they were happy with that, too. In turn, they rewarded him with a loyalty rarely seen in politics these days. Year after year, he had the highest approval ratings of any premier in the country.

In his farewell address in the legislature last December, Mr. Wall said the measure of any governing leader upon retirement is the riposte to the question: Did you leave things better than how you found them? On balance, the answer in Mr. Wall's case is yes. But he unquestionably had advantages his predecessors didn't.

"Not to diminish his contribution to the province in any way, but he inherited a situation that was pretty good," former Saskatchewan NDP premier Roy Romanow told me. "When you come into an economy that is really heating up, with the whole oil boom, it makes the budgeting process a whole lot easier, I can tell you that."

Mr. Romanow would know. When he took over as premier in 1991, the province was on the verge of bankruptcy, a fiscal mess left behind by Conservative premier Grant Devine. The early years of Mr. Romanow's 10-year reign were filled with ugly choices. But setting aside the economic good fortune Mr. Wall had when he took over, he also possessed other qualities that contributed to his phenomenal run of popularity in the province.

"He's a pretty compelling speaker and has a charming personality," Mr. Romanow told me. "He comes across as warm and genuine and people saw that in him even if they disagreed with his policy decisions. I also think he made a point of never ever speaking down to people, he always spoke to them. He also never forgot where he came from, his small-town roots."

And that's important because sometimes the deferential treatment you receive and the trappings that come with the job can make a leader quickly forget his humble beginnings.

During his time in office, Mr. Wall drastically reduced wait lists for surgeries, produced ledgers that earned a Triple A credit rating, indexed the province's minimum wage, got more than 400 people with intellectual disabilities into group homes they needed, fought off a foreign takeover of the Saskatchewan-based PotashCorp. and oversaw record population growth and an infrastructure spending spree that resulted in new schools, hospitals and roadways.

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He accomplished a lot.

Mr. Wall wasn't perfect, though. There were missteps in his government's last austerity budget he had to back down on, such as closing libraries. He's leaving behind a lingering controversy connected to the dubious sale of government land to a questionable mega-mall developer. There is a case to be made that First Nations never got to enjoy the resource boom others in the province did. Mr. Wall's biggest regret, personally, is the fact he's leaving behind a deficit for his successor to clean up.

Likely most of all, however, Mr. Wall will be best remembered for something more ephemeral: the way he made the people in his province feel about themselves and where they live. He made them puff up their chests a bit and give up the "Aw, shucks" routine.

He made them understand it's okay to finish first.

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