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With a quartet of MPPs laying the groundwork for leadership bids, talk is turning to who from outside the Ontario Progressive Conservative caucus might make a play for Tim Hudak's old job.

At the centre of speculation is a familiar face in provincial circles, albeit cross-partisan ones in recent years.

Rod Phillips, until earlier this year the CEO of the Ontario Lottery and Gaming Corp., is known to be actively considering throwing his hat in the ring.

Currently the chair of Postmedia, and last month named chair of the Greater Toronto CivicAction Alliance, Mr. Phillips would offer perhaps the starkest contrast to the former leader he would be seeking to replace – and not just because he didn't serve under him. Ideologically moderate, with a downtown Toronto sensibility despite having grown up in Newmarket, he has more in common with Mr. Hudak's predecessor John Tory, with whom he is friends.

Mr. Phillips, a thoughtful communicator well-liked in Toronto's business and social circles, would garner lots of attention if he were to join the race. He would also face several potential disadvantages relative to his competitors, which could dissuade him from taking the plunge.

The most significant of those is operational. In part because of a close relationship with Paul Godfrey, the Postmedia CEO who served as OLG chair, Mr. Phillips probably would not lack for money or high-level strategic advice. But leadership campaigns are largely about selling memberships, which requires networks of organizers.

To varying extents, the MPPs who appear poised to run – Christine Elliott (the only one to have officially declared), Vic Fedeli, Lisa MacLeod and Monte McNaughton – have had the opportunity to build constituencies within their party. Patrick Brown, a federal MP from Barrie also contemplating a bid, appears likely to inherit some of the social-conservative support that propelled former MPP Frank Klees to second place in the Tories' previous leadership. Mr. Phillips, despite a past in political backrooms both provincially and as chief of staff to former Toronto mayor Mel Lastman, does not have as many on-the-ground connections.

The fact that he has never sought public office previously could also be problematic. Although that lack of experience furthers the contrast with Mr. Hudak, a career politician, it could also make a campaign look presumptuous to MPPs and former candidates whose backing he would need.

On top of that, there is some baggage. At OLG, Mr. Phillips advanced a plan to cut funding for horse-racing, which was a flashpoint for the largely rural PC caucus.

Still, to talk to Tories is to get the sense many aren't thrilled with the leadership options currently on the table. Ms. Elliott could turn out to be the default choice, but amid lingering uncertainty about how badly she herself wants the job (as opposed to the circle of advisers who surrounded her late husband, Jim Flaherty), she has received only modest support from colleagues so far. Ms. MacLeod's boisterous persona has served her well in opposition, but not necessarily helped Tories see her as a potential premier. Mr. Fedeli doesn't get under the skin of as many people, but he's a bit short on allies. Mr. McNaughton, despite obvious potential, is almost unsettlingly youthful, and is closely associated with some of Mr. Hudak's more controversial policies.

Considering the dire shape their party is in – out of power 11 years and counting, down to 28 of Ontario's 107 MPPs, roughly $8-million in debt – there could be appeal in an outsider.

More than one candidate may be able to make that pitch: Rick Byers, a Bay Street executive who has run unsuccessfully both federally and provincially, confirmed in an e-mail that he is also considering a run.

But Mr. Phillips has more profile, and more people seemingly ready to hop on board. He will have to decide whether the race, likely to stretch into next year, offers enough time to overcome his challenges.

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