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Toronto Police Service released documents on Oct. 31, 2013, that show police surveillance photos of Toronto Mayor Rob Ford and Alessandro Lisi, Ford's friend and occasional driver.TORONTO POLICE SERVICE/The Canadian Press

June 26 was a typical day at work for Mayor Rob Ford: He criticized illegal posters that he said blighted the city's bus shelters and utility poles and fended off questions from the media about a controversial assistant. His evening was not that unusual, either – in that it included an out-of-the-way meeting with suspected drug dealer Alessandro (Sandro) Lisi, according to a Toronto police affidavit that was ordered released Thursday.

That evening Mr. Ford drove to one of Toronto's largest parks to watch a child's soccer game, where he was joined on the sidelines by his friend Mr. Lisi, the affidavit states. After a brief conversation, Mr. Lisi retrieved a white plastic bag that "appeared to be weighted" from his car, which he placed, along with some cans of Minute Maid, in the front seat of Mr. Ford's car, the affidavit states.

This sort of encounter between the two men – sometimes at a school parking lot, or in a remote wooded footpath, or with Mr. Lisi dropping an envelope in the mayor's car – is a scene that investigators say played out about a dozen times throughout the summer of 2013. And it kept happening, they allege, even when it became apparent to the mayor and the suspected drug dealer that they were being watched.

Mr. Lisi and the mayor have refused to comment on these meetings. But after secretly observing both men for six months – whether they were watching them from a nearby car, or from the cockpit of the Toronto police airplane, or from a camera mounted near Mr. Lisi's house – investigators came to a firm conclusion: Mr. Lisi is a drug dealer.

"Alexander Lisi is a source of marijuana and has been observed meeting people a number of times in circumstances that would provide opportunities for Lisi to deliver or make drugs available to them," Toronto police Detective-Constable Nader Khoshbooi stated in the affidavit, which was relied upon to execute multiple search warrants, including one at Mr. Lisi's home and another at a dry-cleaning shop that he is alleged to have used as a venue to sell marijuana.

The 474-page affidavit outlines, in painstaking detail, how Toronto police tracked Mr. Lisi and his alleged frequent contacts with Toronto's criminal underbelly, including a convicted killer, petty fraudsters and scores of crack-cocaine addicts. But the bulk of material is devoted to Mr. Lisi's numerous rendezvous with Toronto's chief magistrate, meetings that became more and more clandestine as the investigation progressed. This, in turn, forced the police to reach deep into their bag of surveillance tradecraft, employing all manner of technology, including vehicle tracking devices, phone logs that detailed hundreds of incoming and outgoing calls and surreptitious footage of Mr. Lisi and Mr. Ford captured on store security cameras.

In the early days of the probe, the police employed what they call "static surveillance," a term used to describe basic, in-person observations, usually from the vantage of a car or a rented house. This tactic yielded a few clues about Mr. Lisi's relationship with the mayor: On June 15, Mr. Lisi met with a man that investigators later identified as Mr. Ford's assistant Tom Beyer, the affidavit states; in the days that followed, they saw Mr. Ford drive his car near Mr. Lisi's home, the document alleges. But when Mr. Lisi kept shaking the officers who were tailing him, as Det.-Constable Khoshbooi says, they took to the air and watched him from the force's plane.

And the more they watched, the more contacts they observed. On July 11, officers described seeing Mr. Lisi park his Range Rover at a gas station. He walked to the back of the vehicle and placed something in a manila envelope, which he dropped in the passenger side of Mr. Ford's black Cadillac Escalade, investigators allege. (Mr. Ford was inside the gas station at the time, the affidavit alleges.) On July 28, officers said they watched from the air as Mr. Lisi – carrying a white plastic bag and a McDonald's bag – entered Mr. Ford's Escalade in a parking lot at the Etobicoke high school Mr. Ford attended as a teenager. The two men stayed in the car for a while, before the mayor exited to urinate near some trees, the affidavit alleges. When Mr. Lisi left the car, he discarded his McDonald's bag in a trash can, the document states. There is no mention in the affidavit about what happened to the white plastic bag.

By August, the police say the meeting spots became even more exotic. Only two days after Mr. Ford was accused of appearing intoxicated at a Toronto street festival, a surveillance team followed him to a dirt path near a forest not far from his childhood home, the affidavit alleges. Meanwhile, investigators watched Mr. Lisi park on a different street, and walk down the same footpath. The two men talked in the "secluded area" for about an hour before they went back to their vehicles, the document states. When investigators descended on the scene of their chat, they found an empty vodka bottle and an empty juice bottle. (They seized the trash but replaced the empty bottles so that no one would know the originals were seized, the document states.)

But in mid-August, only a day after the first media reports revealed that police were prying into the nature of the relationship between the two men, the duo was on high alert, the document states. On Aug. 18, during yet another meeting at Mr. Ford's old high school, something caused them to be suspicious about the police surveillance vehicle that was watching the pair, the affidavit alleges. As the undercover police car slowly made its exit, Mr. Ford "was observed continuing at a high rate of speed north on Duffield Road, the last known direction of the surveillance vehicle," the affidavit states.

The investigators later received a phone call about the incident from the mayor's chief of staff, Earl Provost, who they say wanted to know about a vehicle that was following the mayor. Mr. Provost provided a license plate number, but when the police refused to provide the information, Mr. Provost said that the mayor was "getting angry… because he can't give him what he wants," the affidavit states.

The investigators concluded that the efforts to retrieve the vehicle's registration information was evidence of Mr. Ford "utilizing his position and the powers of the Office of the Mayor, to obtain information not available to regular citizens."

With a report from Jill Mahoney