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Potential Liberal leadership candidate, Former MP Gerard Kennedy after his defeat to NDP candidate Peggy Nash for Parkdale High Park in the federal election May 2, 2011. (Moe Doiron/The Globe and Mail)
Potential Liberal leadership candidate, Former MP Gerard Kennedy after his defeat to NDP candidate Peggy Nash for Parkdale High Park in the federal election May 2, 2011. (Moe Doiron/The Globe and Mail)

Kennedy supporters try, and fail, to gauge support for a leadership run Add to ...

The e-mail, titled “Liberal Vision,” arrived in the inbox of Ontario government staffers around lunch hour on Friday afternoon. After informing recipients that Gerard Kennedy is “still considered by the general population as the best candidate for leader of the OLP,” it extended an invitation to attend an open meeting on Saturday, so he could gauge support for a leadership bid and “assess where your help can best be utilized if he decided to run.”

Less than an hour later, the same staffers got another e-mail from the same person, telling them they should “ignore and discard” the first one, which was “sent by someone who should have known better.”

That’s a description that some Liberals are also currently applying to Mr. Kennedy, a former star having difficulty letting go of his hope to replace Premier Dalton McGuinty – the man who beat him out for the provincial Liberal leadership 16 years ago.

On Friday, a source close to Mr. Kennedy said he’s currently “about 50/50” on whether to run, while acknowledging that he’s leaning more toward it than he was a week or two ago. And it’s easy to see why there are those encouraging him to go for it, a message he’ll no doubt hear at Saturday’s meeting (which is still supposed to proceed, albeit without the government staffers who were invited accidentally).

The 52-year-old former food-bank director, provincial education minister and federal MP remains among the best-known Liberals in the province. He has a reputation for working exceptionally hard, and is still possessed of a certain charisma that delivered him a following back in the 1990s. And, unlike anyone else considering a provincial leadership run, he’s been away from Mr. McGuinty’s government for long enough to have some real distance from its baggage.

The catch is that, however good a leader he might be for the Liberals, it’s very difficult to imagine him winning the job; for a variety of reasons, his would-be campaign has the potential to be a kamikaze mission.

To begin with, there’s the fact that his constituency in the party has at least partly been taken over by someone else. In that 1996 leadership contest, which Mr. Kennedy led on the first ballot, he was the only candidate representing the Liberals’ left flank. This time around, veteran cabinet minister Kathleen Wynne is occupying much of that space, and has already locked up some of the available supporters.

A bigger constraint is that, while he has his admirers, there are also a lot of provincial Liberals who flat-out dislike him – recalling him as a loner who didn’t play well with others, and complaining that he’s done a poor job maintaining relationships since he left Queen’s Park during Mr. McGuinty’s first term. It also doesn’t help that he’s still remembered as the 2006 federal leadership candidate who played kingmaker for Stéphane Dion. So even if he did reasonably well on the first ballot of January’s delegated leadership convention, he would have big trouble trying to win the second- or third-choice support needed to put him over the top.

Both of these hurdles might conceivably be surmountable if Mr. Kennedy had really great resources. But many of the people who helped him out previously, including his former campaign manager and his top suburban organizers, are committed to Justin Trudeau’s federal leadership campaign and wouldn’t come back for him. And having only cleared up his federal leadership debt quite recently, it’s an open question how much money he could raise.

It is not hard to find Liberals – even those who aren’t his biggest fans – who think Mr. Kennedy still has a future in public office down the line. But having unsuccessfully contested two leaderships, and then having lost his federal seat in last year’s election, he’s in danger of burning whatever political capital he has left.

That he’s strongly considering taking that risk is a reminder of how hard it can be to shake the political bug. Mr. Kennedy started running 16 years ago, and he’s still having trouble stopping – even when he faces a steep uphill path in front of him.

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