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A man walks in the revitalized downtown core of Windsor, Ont., September 2, 2011.

Sandra Pupatello hadn't even ordered her breakfast yet when the elderly owner of the downtown diner descended on her table.

It was evidently the first time he had seen her since she announced an end to her 16 years in the provincial legislature, and he had some strong feelings to get off his chest. "You're making me so sad!" he exclaimed.

Dalton McGuinty might well have had a similar reaction, back when his Economic Development Minister gave him the news a couple of months earlier. With the election writ about to be dropped, what was once one of the few safe Liberal seats in the province is now up for grabs.

Losing incumbents before an election, as Mr. McGuinty's Liberals have in 14 of the 72 Ontario ridings they currently hold, never helps a government's chances of winning another term. But rarely does it sting quite as badly as in the case of Ms. Pupatello.

There is something a little strange about Windsor's relationships with its politicians. Few places in Ontario have seen as much economic turbulence, which can often make for short political careers. But this is a town that loves its incumbents.

Mention their first names around town, and people will know who you're talking about. Eddie Francis, the third-term mayor, is "Eddie." Dwight Duncan, the provincial Finance Minister who has represented one of the city's two ridings since 1995, is "Dwight." Ms. Pupatello, who represents the other one, is "Sandra."

But for all the loyalty toward incumbents, it doesn't seem to carry over to their parties.

For four decades, Windsorites sent Herb Gray to Ottawa – making the former Liberal cabinet minister and deputy prime minister the longest-serving MP in Canadian history. But when Mr. Gray retired in 2002, the Windsor West riding suddenly swung to the NDP. Since then, New Democratic MP Brian Masse has increased his share of the popular vote in every election.

All three major parties have every reason to fight hard for the riding in this election, knowing there's a pretty good chance of putting a lock on it for many years to come.

The issue that matters: jobs

As anywhere else in the province, health care, education and pocketbook pressures will be the subject of debate between the parties. But according to Mr. Francis, the 38-year old mayor whom both parties reportedly tried to recruit as a candidate, it will all just be a "distraction" from the one issue that matters: jobs.

Contrary to popular belief elsewhere in the country – fuelled partly by the fact that it borders on Detroit, the epitome of urban woe – Windsor is not a city in the midst of collapse. (It bears noting, here, that as of this summer Windsor had not had a murder in nearly two years – a remarkable run considering what's happening across the river.)

The unemployment rate, which peaked at 15.2 per cent in July, 2009, dipped to 8 per cent two years later. While there's room for debate as to the quality of that employment, there's a sense that Windsor has turned the corner since the 2008-09 recession that threatened to permanently decimate the auto industry around which the city's economy was built.

That industry is surviving, if not thriving, in part because of the bailout provided by the federal, provincial and U.S. governments. But Mr. McGuinty's Liberals will lay further claim to the recovery.

While their green energy policy has caused friction elsewhere, this is one place where it might be celebrated. As the city has cast about for ways to transition its manufacturing industry, wind and solar power have created hundreds of jobs for the Windsor area, with thousands more supposed to come.

Meanwhile, the province has committed millions upon millions to other local employers creating green-tech jobs – from clean-water technology to electric cars. And together with other levels of government, it pumped billions of dollars of infrastructure stimulus spending into the city, including an ongoing revitalization of its downtown.

But for all that, it's hardly a boom town just yet. Some Windsorites are working new jobs that pay less than their previous ones; others are in the same old jobs, with flat-lined salaries. If the metrics have improved, it hasn't always trickled down to people's lives.

Both provincial opposition parties will try to play off that. The Progressive Conservatives, in particular, will argue that Mr. McGuinty's green energy push will actually cost more local jobs than it creates by pushing hydro rates to a level that other businesses can't afford. The Liberals, in turn, will contend that changing course just as things have turned around could have disastrous consequences.

No household names

The Liberals did not line up a household name to fill their sudden vacancy. Having worked until now as the City of Windsor's executive director of employment and social services, Teresa Piruzza knows well what her city has been through. And having previously worked as a constituency assistant and campaign manager for Ms. Pupatello, she's no stranger to Windsor's politics. What she lacks, at least on first impression, is the incumbent's outsized personality.

But then, Ms. Pupatello shrewdly waited until close to the election before signalling her exit – too late for the other parties to lure star recruits of their own.

Progressive Conservative candidate Todd Branch appears to be running an impressively energetic campaign, considering that his party hasn't won here since the 1960s. The private-practice lawyer will make the pitch that, with Tim Hudak's party leading in the polls, Windsor needs to elect a Tory in order to retain a strong voice in government. But efforts to recruit Mr. Francis as a candidate, once Mr. Branch had already been nominated, suggest the central PC campaign is unconvinced he can capitalize on Ms. Pupatello's absence.

If there's a household-name-in-the-making, it's probably Helmi Charif. The NDP candidate, a long-time NDP activist and local businessman who came to Canada 20 years ago, teeters somewhere between engaging and a little too solicitous. (He's the sort of guy who, within a couple of minutes, will offer a visiting journalist a tour of his hometown in Lebanon and a good price at his car dealership; while he's probably joking about both, you can't be completely sure.)

Mr. Charif ran in the last election against Mr. Duncan in the neighbouring riding, and his ties to the large Arab community should help to offset the Liberals' traditional support among Italian-Canadians.

Still, unfamiliarity with all candidates will make this the rare Windsor election that's largely about the party leaders – and that should be worrisome for Mr. McGuinty in particular.

While NDP Leader Andrea Horwath has worked Windsor hard, making repeat visits, the Premier has habitually left it to Mr. Duncan and Ms. Pupatello to carry the Liberal banner. That means his profile in the city, for all the money his government has poured into it, is fairly low.

"He's got to come down here and establish a relationship with the community," Mr. Francis says. "He can't just leave it to Dwight."

Mr. Francis stresses that it's not just the Premier; all three leaders must work to raise their local profile.

But if the Premier has indeed taken Windsor for granted, or at least assumed that his ministers have had it well-covered, he will no doubt be making up for lost time over the next month. Because history shows that once you lose Windsor, it's awfully hard to get it back.

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