Why the Tories' Jamaican spy mission against Bonnie Crombie is a headache for Doug Ford

A day after Premier Doug Ford took aim at his own party’s decision to use taxpayer-subsidized funds to spy on then-Liberal leader Bonnie Crombie during her Jamaica vacation, some Tories are questioning whether the gambit had any value at all.

“It’s still not clear what we were hoping to achieve getting a picture of Bonnie Crombie on the beach. It’s a lot of money to spend for a photo,” said one senior Tory insider, who spoke confidentially in order to discuss internal deliberations.

But in December 2023, the Ontario Liberals had just elected the high-profile Mississauga mayor as their leader and Ford’s Tories were spooked.

Crombie was living rent-free in the premier’s head and Greater Toronto Area PC MPPs were equally concerned that she might break their electoral stranglehold on the 905.

So when the Tories — who were preparing a multimillion-dollar attack advertising blitz to dust up the new Liberal leader — were tipped off that she was flying to Jamaica at the last minute for a long weekend before Christmas, they pounced.

Tory sources, who spoke confidentially because they were not authorized to discuss internal matters publicly, say the party decided to dispatch an operative to follow Crombie in a bid to capture photos of her and her then boyfriend living the high life.

Insiders say such images would have bolstered their planned ad campaign painting the Liberal leader as a wealthy elite who was out of touch with the concerns of ordinary Ontarians.

The unnamed operative failed to get anything useful on the Jamaica jaunt, but the Tories went ahead with attack ads against Crombie using a photo taken in Toronto of her exiting her then boyfriend’s Maserati Ghibli sedan.

Ford’s party was easily re-elected in February 2025, while Crombie stepped down as leader after failing to win a seat and suffering a lacklustre Liberal leadership review result.

The covert surveillance mission might have been forgotten had the party not filed $3,000 in expenses, detailing the Jamaica trip on its 2023 financial statements as an “office and administration” cost, an unusual item noticed by news outlet The Trillium with follow-up reporting from Policorner and Queen’s Park Observer.

That embarrassing disclosure eventually forced the Tories to acknowledge they had paid to spy on Crombie overseas — and insiders confide that they also spent tens of thousands of dollars conducting “opposition research” on the Liberal leader here in Ontario.

It has also exposed friction between the premier and the party he leads.

“Talk to the party. I don’t approve of it. That was $3,000 of the party’s money,” Ford said dismissively Thursday, insisting he only recently learned of the Jamaica mission, which was the subject of rumours and tweets, including a cryptic post of the Jamaican flag from his then head of issues of management upon Crombie’s return.

While the premier shrugged off the spying and the expense by saying “stuff happens during the elections,” the trip was 14 months before the vote and the funds used were subsidized by taxpayers.

That’s because the money came from PC supporters, who receive tax breaks for their donations, and from the $2.54 in public subsidies that every party gets annually for each vote it receives.

“Ford didn’t know (about the Crombie surveillance), but I don’t get why he would throw the party under the bus,” said the senior Tory insider.

“He’s the leader, it’s his party.”

Peter Turkington, the PC party’s director of communications, defended the move.

“The Ontario PC Party, like other political parties, conducts opposition research. In this instance, that work included travel to Jamaica in December 2023,” said Turkington.

Nick Kouvalis, Ford’s pollster and one of the key architects of the premier’s election victories, took to social media to denounce the trip.

“I didn’t know anything about it until after the fact. I wasn’t running political operations for the PC Party. And, the political operation guys at the time didn’t care to consult with me, ever, on anything,” said Kouvalis.

Behind the scenes, there are questions about why the Tories would even expense such a trip in a way that might raise red flags for reporters poring over financial statements.

For such “black ops,” political parties traditionally bury the costs in their filings so they cannot be easily detected. This can be done by including them under opaque categories or by using contractors who might bill for services using vague descriptions.

But the Tories’ 2023 statement specifically listed the names of two hotels expensed in Jamaica. 

“It’s hubris,” sniffed a second Tory insider, lamenting the “stupidity” of those involved.