Even Gerard Kennedy's longtime supporters look back on his last leadership convention - or at least, one particular aspect of it - with a tinge of embarrassment.

More than likely, Kennedy would have lost the Ontario Liberal leadership anyway; having vaulted from head of Toronto's Daily Bread Food Bank to the front-runner on the first ballot, he was the inevitable target of an "anybody but Kennedy" movement in other leadership camps stocked with party veterans. But it was the video that accompanied his convention speech that was probably the final nail in the coffin.

To the strains of U2's One, delegates were treated to a montage of human suffering - homelessness, mostly - designed to show the horrors of the Mike Harris era. Interspliced were shots of Kennedy looking earnest, and a quick flash of a certain former prime minister intended to drive home the message that the provincial Liberals had found their answer to Pierre Trudeau.

Among Liberals' suspicious of Kennedy's sudden emergence as their party's golden boy, it was taken as proof of the messiah complex they'd been whispering about for months. Although more the handiwork of his campaign team than Kennedy himself, the video fit the caricature of a candidate who'd come off as aloof and self-righteous during the campaign.

In the decade since, Kennedy has done much to change that image. Defying accusations that he had no interest in the provincial Liberals beyond his own leadership aspirations, he worked diligently in opposition to help get Dalton McGuinty into the premier's office. After the Liberals won office in 2003, he emerged as arguably the government's most popular and successful minister - not least because of a friendly working relationship with McGuinty.

And yet, as he rides into another Liberal leadership race as the white knight - this time on the federal level - Kennedy will need to dispel the same bad rap he failed to dispel the first time.

Confronted with his lack of experience in federal politics, Kennedy's supporters are quick to point out that he's virtually the only contender for Paul Martin's job without any baggage.

Strictly speaking, that's true: Kennedy was never a New Democrat (Bob Rae) or a Conservative (Scott Brison), he's never been accused of links to an income trust scandal (ditto), and he didn't support the Iraq war (Michael Ignatieff). Of the candidates who actually have a chance to win, only Ken Dryden can claim as clean a slate.

The one thing that Kennedy must overcome, though, is in some ways more challenging than standard baggage. Somehow, he needs to avoid rubbing people the wrong way.

There are many, many provincial Liberals who like their erstwhile former education minister. They admire his impeccable work ethic, his strong liberal values, and even the boy-scout naivete that sometimes makes him seem apolitical 10 years into his political career.

But what is endearing to idealists can be anathema to jaded political types - and there are a lot more of the latter than the former in the upper echelons of the federal Liberal party.

They expect their leadership candidates to be good gladhanders, to kiss the right rings, to make pragmatic choices and to be easy to work with. None of those tags exactly fits Kennedy. He's awkward in crowds, he forgets people's names, his listening skills are less than stellar, and he has a reputation for being rough on staff - not so much because of a temper, but because he expects them to match his slavish commitment to work.

Even Kennedy's integrity can be a downside. Long past his food-bank days, he still sees himself as more community servant than politician - insisting, for instance, on devoting far more time to local issues than your average minister. Whereas most politicians in his shoes would hold onto their provincial seats until they saw how their federal aspirations played out, he's planning to resign his because he doesn't want to under-represent his riding in the interim.

Perversely, that sort of persona will rub more pragmatic types the wrong way. At some level, it feels like he's trying to show them up - and nobody likes a candidate who makes them feel inferior.

There are, too, legitimate questions about how his skills will translate nationally. Being a micromanager can be an asset provincially - certainly in the education ministry, which needed close attention. But at the federal level, more about setting general directions than managing the minutae of social policy, taking a step back is imperative.

That last one, though, will be for Kennedy to worry about if and when he gets there. For now, he needs to make a good first impression on the nine provinces where nobody much knows who he is, and where his opponents will be trying to paint him with the same brush as in '96.

An early word of advice for his campaign team: Don't show that convention video again.