Their side-by-side appearance to announce billions for public transit in that city, complete with an almost-endorsement from Toronto's mayor, had all the usual hallmarks of an election-campaign event.
For Oliver, it was.
At 75, Oliver might be forgiven if he was among the more than three dozen MPs not running run for re-election this fall, but he's raring to go.
"I'm ready to present myself to the people," Oliver said this week.
"(It's) an extraordinary opportunity for me in the Finance portfolio to be able to contribute to Canadian society in a way which touches virtually every Canadian."
Oliver was among a number of Toronto-area candidates with impressive private sector pedigrees who ran for the Conservatives in 2011, including Chris Alexander, a former Canadian ambassador to Afghanistan; and Kellie Leitch, a pediatric orthopedic surgeon.
It was proof, the Conservatives said at the time, that their party had the chops to attract the cream of the private-sector crop.
But more than two dozen Conservatives aren't running for re-election this time, including cabinet leaders like Peter MacKay and John Baird and relative newcomers like Shelly Glover, who had been considered a rising star, raising questions about where the party is looking to rebuild the capacity of its front bench.
In the Toronto area — a key battleground come October — most of the incumbents are running again, leaving little room to recruit new stars.
But in Quebec, there's a wide-open playing field — the Conservatives currently have only five MPs out of 78 available seats in the province — and the party has been able to lure several heavy hitters to the team.
Dominic Therrien is a former player for the Atlanta Braves baseball team turned immigration lawyer running in the riding of Trois Rivieres. Marc Dauphin once ran the military hospital in Kandahar and is now running for the Conservatives in the riding of Sherbrooke.
And while a successor to current cabinet minister Christian Paradis has yet to be officially nominated, when Paradis announced in April he wasn't running again, many Conservatives actually considered it good news — another likely seat they'd be able to fill with a high-profile hopeful.
"We're able to attract star candidates and that's a good sign," Maxime Bernier, a longtime Conservative MP from Quebec said this week.
"It shows that we are the party that is meeting people's expectations."
Many of the MPs who've chosen not to stand for re-election have cited family concerns or a desire to return to their former jobs, like Glover, who is going back to police work.
But the opposition says it is proof the air is out of the Conservative sails and that many Tory MPs are taking the money and running, fearful their time in government is up.
MPs who stay until the end of their terms, but don't run for re-election, are eligible for a generous severance package, worth about 50 per cent of their salary. For those who stay, there are also financial realities at play: MPs must serve six years in order to qualify for their pension.
That means Oliver won't qualify until 2017.
Polls suggest support for the Conservatives has softened. Where they were once reliably capturing more than 30 per cent of popular support, some surveys earlier this month put the number below that marker.
High-profile departures bolster the perception of decline, said pollster Donna Dasko, a former senior vice-president at Environics.
"If I were them I would be getting really worried about all this," she said. "They should be worried about that. It's now very much in dangerous territory for them."
— with files from Bruce Cheadle
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