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Liberal candidate Rolf Dinsdale greets supporters at his party during a tight by-election in the Brandon-Souris area of Manitoba on Nov. 25, 2013. Mr. Dinsdale would wind up losing the by-election seat to the Conservative candidate, Larry Maguire.TREVOR HAGAN/The Canadian Press

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The Liberals hold two seats across the Canadian prairies. With that in mind, the party's losses in Manitoba's by-elections this week might not seem surprising. So why does Liberal candidate Rolf Dinsdale feel, in his words, like a climber who turned back with Mount Everest's peak in sight? Because his riding was winnable.

Circumstances were ripe for an upset, but the Liberals fell short in Brandon-Souris. The Tory stronghold was opened up with the resignation of Merv Tweed, then things got messy. A disputed Tory nomination process saw Mr. Tweed's aide frozen out; the Senate scandal was swirling; the federal NDP vote was set to slump, perhaps in part because Manitoba's NDP provincial government had hiked the PST; and the Liberal candidate had a familiar name because his father had won the riding 12 times.

All told, Justin Trudeau's team had an opportunity to deliver a blow in the Tory heartland. Public opinion polls showed the Liberals leading, but have been criticized as inaccurate. Regardless, all indications were that the Liberal threat was real. After all, the Conservatives dispatched Jenni Byrne, who led their entire 2011 federal campaign, to the riding for over a week. In the end, Conservative Larry Maguire beat Mr. Dinsdale by 391 votes.

So did the Liberals miss an opportunity, or blow it? They actually got some good news, but let's start with the bad. There were missteps, some outlined here by Deveryn Ross in the Winnipeg Free Press.

For one, Mr. Trudeau didn't visit the riding in the campaign's final days, and didn't ever visit many smaller towns in Brandon-Souris, including Souris itself. One Conservative, though, doubts a fifth visit would have led to a win. "If Trudeau lived here, I don't think they would have found 391 votes," the source said.

In one gaffe, Mr. Trudeau was criticized for discussing marijuana policy while visiting students in the riding. Further, the Liberals lacked, in campaign-speak, a ground game. "They just didn't have enough people to push out," a Conservative said.

Then there's Rick Pauls, mayor of small-town Killarney, who was considering running as an independent conservative amid the messy Tory nomination process. But the Liberals wanted a nomination battle, one party source said, presumably so they could attack the Tory process. So Mr. Pauls ran instead for the Liberal nomination, nearly driving Mr. Dinsdale to quit; Mr. Dinsdale didn't, and ultimately won. Then Mr. Pauls more or less disappeared.

His candidacy as an independent could have made a difference, though what difference is unclear. In Killarney, Mr. Maguire got 427 votes and Mr. Dinsdale got 226. Mr. Pauls would have been a wildcard.

Meanwhile, the Conservatives sought to calm unrest from their nomination debacle. Another challenger, Mr. Tweed's staffer Chris Kennedy, had been first out of the gate, but claimed he was frozen out by the party when it didn't accept his paperwork. Then Derryk Jackson, a Conservative who said he'd worked for Mr. Kennedy before supporting Mr. Maguire, later said Mr. Kennedy didn't get his documents in on time. A third candidate dropped out.

"The process was not flawed. The process was there and it was abided by," Mr. Maguire says. "... For whatever reason, it took quite a while for the truth to come out, and that's been a situation that needs to be, perhaps, clarified. But it's not something I can do anything about."

It all raised questions of top-level party interference, emphatically denied by the Maguire camp but familiar to former Manitoba MP Inky Mark, a Conservative who complained about party interference in the nomination process that followed his retirement in 2010.

"Basically they didn't want anybody to be nominated other than their candidate of choice," Mr. Mark, who has since emerged as a critic of Prime Minister Stephen Harper, said of the party's role in his riding. "Everything that Harper's been doing is anti-democratic... History always shows us that governments defeat themselves, and leaders defeat themselves through their own behaviour. So he has nobody to blame but himself if the whole thing collapses."

So Conservatives were upset and the NDP vote was collapsing. In the end, the New Democrat candidate got 7 per cent of the vote in a riding the party finished second in last time around.

But Mr. Maguire had some help, aided by the Liberals' selection of Mr. Dinsdale. The Conservatives attacked Mr. Dinsdale for only recently moving back to the riding ("He only came back to get elected," an attack Michael Ignatieff might find familiar) and for the tongue-in-cheek song titles, such as "Jesus got Wood," of Mr. Dinsdale's band. Mr. Harper also wrote a letter to the supporters in the riding. With Ms. Byrne leading the way, it was enough. "Despite the smug and breathless punditry... the columnists and media elites were proven wrong again," Conservative Party spokesman Cory Hann said.

For all the potential missteps, Mr. Dinsdale says he's not looking back. He plans to run in 2015. "In an election, many, many things go your way. Many, many things screw up. We had our share of good fortune, and stepping in puddles. We can't think that this or that might have been the difference," he said. "... I know I campaigned as hard and well as I could."

This brings us to the good news. Poll-by-poll results compiled by Elections Canada show the Liberals lost narrowly across the entire riding, but dominated the polls in Brandon – the city that's the hub of the riding. In Brandon, Mr. Dinsdale drew 6,551 votes, ahead of Mr. Magurie's 3,834. In other words, the Liberals outpaced the Tories by about 71 per cent in the city.

The 2015 federal election will feature a new electoral map, one where 30 seats have been added in mostly urban areas. Boundaries have also changed. In Saskatchewan, for instance, hybrid rural-urban ridings have been done away with. Altogether, the electoral voice of cities is increasing, and in Brandon, the Liberals showed this week that even Prairie cities aren't necessarily Tory strongholds when the circumstances are right.

Josh Wingrove is a parliamentary reporter in Ottawa.