Doug Ford Says He Didn’t Know. Who Did?

Doug Ford would like the story of his party sending someone to Jamaica to surveil Bonnie Crombie to be treated as one of those strange things that happens in politics.

“Stuff happens,” the Ontario premier told reporters Thursday.

Except this particular stuff required somebody to make a decision.

Someone inside the Ontario Progressive Conservative Party knew where Crombie was going. Someone approved sending a person to Jamaica. Someone authorized the spending. Someone presumably decided what the researcher was supposed to look for, and someone would presumably have expected to receive whatever information came back.

More than 24 hours after the story broke, we still don’t know who that was.

Ford says it wasn’t him.

According to the premier, he only learned Wednesday that his party had sent someone to Jamaica in December 2023 to monitor Crombie while she was on vacation. He says he didn’t approve of the operation and has since spoken to the party about it.

There is currently no public evidence establishing that Ford knew about the operation beforehand. There is also no independent evidence establishing that he didn’t. At the moment, his lack of prior knowledge is Ford’s account of what happened.

That makes the oldest question in political accountability the appropriate one here: what did the premier know, and when did he know it?

The timing of the original operation makes that question more interesting.

Crombie became leader of the Ontario Liberal Party on December 2, 2023. The Progressive Conservatives didn’t wait to see what kind of leader she would become. They began attacking her immediately.

On the same day she won the leadership, the Ontario PC Party issued a statement portraying Crombie as an out-of-touch elitist who drove expensive cars, raised taxes and vacationed at a home the party incorrectly described as being in the Hamptons. Within weeks, television and radio attack ads were running against her. The Canadian Press noted at the time that such advertising would normally be expected closer to an election, not two and a half years before one.

Meanwhile, something considerably more unusual was happening.

Crombie travelled to Jamaica days after becoming Liberal leader. PC Party financial records subsequently showed spending of roughly $3,000 at two Jamaican resorts, including a payment at the resort where Crombie was staying. The party has now acknowledged that its opposition research included travel to Jamaica in December 2023.

Whatever anyone thinks of Crombie today, the political context of December 2023 is important.

She wasn’t yet the Liberal leader who would lose the 2025 election and fail to win her own seat. None of that had happened. She was the former mayor of Mississauga, a former federal MP and the newly elected leader of a provincial Liberal Party trying to recover from two disastrous elections.

More importantly for Ford, Crombie came from the 905.

The Progressive Conservatives had good political reasons to take her seriously. The suburban voters around Toronto who had helped Ford build his majority were precisely the sort of voters a centrist Liberal with an established political base in Mississauga might have been able to reach.

Taking a new opposition leader seriously is hardly scandalous. It’s what competent political parties do.

But the intensity is striking.

The PCs weren’t merely preparing arguments against Crombie. They attacked her on the day she became leader, quickly launched paid advertising against her years before the scheduled election, and, according to the party’s own confirmation this week, their opposition research operation followed her to Jamaica.

That behaviour suggests the PC political organization regarded Crombie as a potentially serious threat almost immediately.

Which brings us back to Ford.

The premier says he knew nothing about the Jamaica operation until this week. That may be exactly what happened. But accepting Ford’s account still leaves an unusual picture of how the political organization surrounding him was operating.

This wasn’t a junior researcher searching Crombie’s old tweets.

Travel had to be arranged. Money had to be spent. A person had to know where Crombie would be and when she would be there. Somebody had to decide that following the newly elected Liberal leader outside Canada was worth doing.

Who made that decision?

There’s another detail that makes an answer more necessary. Ford’s office has said that anyone involved in the Jamaica operation no longer works for the government or the party.

That’s a surprisingly definitive statement from an organization that says its leader only learned about the operation this week.

If Ford’s office knows that everyone involved is gone, then someone presumably knows who was involved. The public still doesn’t.

There is one additional name in the reporting that deserves careful attention, although not accusation.

Cody Welton was Ford’s deputy chief of staff at the time, with responsibilities that included issues management, media relations and legislative affairs. On December 11, 2023, the day Crombie returned from Jamaica, Welton posted a Jamaican flag emoji on X. The post was later deleted. When The Trillium asked Welton whether the post was connected to Crombie’s trip or whether he had been involved in the operation, he did not respond. There is currently no evidence establishing that Welton authorized the trip or received information from it, and the coincidence shouldn’t be presented as proof that he did.

It does, however, add another unanswered question to a story already full of them.

Who did the person in Jamaica report to?

Ford’s response so far has largely avoided that chain of command. He has defended opposition research generally and suggested these things happen in elections.

There wasn’t an Ontario general election underway when this happened. Crombie had been Liberal leader for less than two weeks, and the next scheduled provincial election was still years away.

The eventual election tells us something else about how seriously the PCs had reason to take her at the time.

Ford ultimately called an early election for February 2025 and won another majority. Crombie’s Liberals improved their seat count and regained official party status, but Crombie herself lost in Mississauga East–Cooksville. Her leadership subsequently unravelled.

Looking backward, it’s easy to conclude that she was never much of a threat to Ford.

The people running the Ontario PC political operation in December 2023 couldn’t possibly have known that.

Their behaviour suggests they weren’t willing to take the chance.

None of this proves Ford knew about the Jamaica operation. Suspicion isn’t evidence, and Ford’s reputation as an engaged political leader isn’t proof that every decision made inside the PC organization crossed his desk.

But his denial doesn’t answer the larger question either.

If Ford knew, Ontarians deserve to know what he knew and when he knew it.

If he genuinely didn’t know, Ontarians deserve to know who within the political organization he leads had enough authority to send someone out of the country to follow the newly elected leader of an opposing party without telling him.

Either explanation leads to the same place.

Someone ordered the Jamaica operation.

Someone knew.

More than two and a half years later, we still don’t know who.