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Tim Hudak had the look of an unhappy man doing his very best to look happy.

Meeting reporters on the morning after Ontario's summer by-elections, the Progressive Conservative Leader gamely proffered his best spin. Sure, the Tories had only won one of five ridings up for grabs. But they broke through in Toronto, for the first time in over a decade; they received more cumulative votes than any other party; the Liberals, who lost three of five seats they had long held, were sent a message.

All this was true. But as Mr. Hudak was no doubt aware, it wasn't enough for the critics within his own party, or the right-wing talk radio hosts, or the chattering classes, who all demanded more from him. By the time he took to the microphone, the narrative was already taking hold that votes which days earlier had offered him the promise of some redemption instead represented just his latest failure.

Such is Mr. Hudak's lot in life. He is bearing the burden of a party that has been out of power for a decade – a stint that, before the end of this calendar year, will become its longest in the political wilderness since the Second World War. He is doing penance for extending that streak with an awful introduction to voters in his first election at the helm. And when he tries to prove to his fellow Tories that they're finally on the verge of turning the corner together, sometimes he just makes things harder for himself.

In this case, Mr. Hudak suffered from raising expectations, or at least allowing others to raise them on his behalf.

The Liberals began the by-election campaigns hoping to win back three or four seats, but by the end were braced – and had braced others – for the likelihood they would only win one or two. By contrast, the Tories started off knowing there was a chance they could get skunked altogether, but by the end were making little secret of their belief that they had momentum, positioning themselves as the beneficiaries of voter unrest over the Liberals' gas-plants scandal.

The recruitment of Toronto deputy mayor Doug Holyday to run in Etobicoke-Lakeshore helped raise the stakes. It was an impressive coup that led to the Toronto breakthrough. It also belied any attempts by Mr. Hudak to play down the significance to him of these votes. And because Mr. Holyday was the only of the five PC candidates to win, the ensuing perception is that Mr. Hudak was spared humiliation by someone who, standing alongside him Friday morning, looked rather like a kindly uncle.

In truth, of the four ridings his party didn't win on Thursday, only one really merits serious soul-searching. Windsor-Tecumseh was an NDP lock from the outset; Scarborough-Guildwood wasn't going to shift away from the Liberals unless the Tories had major star power; Dalton McGuinty's old seat of Ottawa South was competitive, but the organization left behind by the former premier was hard to beat. That the New Democrats were able to cruise to a second win when the Liberal candidate tanked in London West, a swing riding that normally tilts centre-right, is tougher to explain away.

That alone shouldn't be enough to keep Mr. Hudak up at night. But by most appearances and accounts he is someone who wants badly to please, to reward the faith others placed in him when they elected him party leader, and there is no doubt that it stings every time he gives his doubters fresh fodder.

No wonder that, even if this week offered another setback, Mr. Hudak continues to clamour for a general election at the first opportunity. If he's able to reintroduce himself as the serious-minded conservative he failed to prove himself the first time around, and voters embrace it, he'll be the province's next premier; if he loses, it will be someone else's turn to carry the weight of Tory expectations. Either way, it will be an end to the purgatory in which he currently finds himself.