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Alessandro (Sandro) Lisi, with his lawyer, Seth Weinstein, is escorted out of Old City Hall Court in Toronto on Nov. 1, 2013.PETER POWER/The Globe and Mail

Toronto police are zeroing in on Alessandro Lisi's cellphone conversations with Toronto Mayor Rob Ford and two of the politician's former staffers in a sweeping probe that began after reports emerged of a video allegedly showing the mayor smoking crack cocaine, court documents reveal.

Mr. Lisi, a friend of the mayor and his former driver, is facing an extortion charge related to an alleged attempt to retrieve the Ford video in May of last year. A police affidavit, submitted to court on March 7 to obtain a warrant for data from Mr. Lisi's iPhone, shows investigators wanted to view text messages, photos, video and audio recordings taken or relayed on Feb. 17, 2013 – the day that police believe the Ford video was filmed – as well as afterward.

Police were also seeking Mr. Lisi's communication with the mayor, Mr. Ford's friends Fabio and Elena Basso, and two of the mayor's former staff members, David Price and Tom Beyer, states the affidavit released by the Ontario Superior Court on Monday. Of interest to investigators, too, are Mr. Lisi's cellphone conversations with three men believed to have tried to sell the Ford video to several media organizations.

Two of the men, Mohamed Siad and Liban Siyad, are accused of belonging to an Etobicoke gang known as the Dixon City Bloods. Police allege Mr. Lisi threatened the pair, who were among about 60 people arrested last year in a guns-and-drugs investigation known as Project Traveller.

In the affidavit, police allege wiretap surveillance of the gang picked up conversations and text messages about the mayor and "his involvement with drugs" last March, two months before reports of the video surfaced on May 16, 2013.

"Because of the involvement of drugs, the Mayor and the necessity to investigate the content of the intercepts, Project Brazen II was developed," the document states. "The mandate was to investigate any criminality that may exist that might be associated with the Mayor or his office while ensuring that the integrity of Project Traveller remained intact."

The affidavit notes that more than 100 text messages were sent or received by Mr. Lisi on May 18. Police allege Mr. Lisi, 35, attempted to secure the Ford video then.

The investigation of Mr. Ford, who is seeking re-election in October, has upended city hall and drawn international attention. The allegations against the mayor and Mr. Lisi have not been tested in court and the mayor has not been charged. Mr. Lisi, who also faces several drug-related charges, is known for making secret video and audio recordings of his interactions with others.

Police have so far sought seven search warrants in connection with Project Brazen 2. Lawyers representing several media organizations including The Globe and Mail have asked the court to unseal information used to obtain the warrants. Some portions remain under a publication ban. Further arguments are scheduled to be heard on March 28.

An affidavit released last week offered the first official police description of the infamous Ford video. The one-minute recording was found on a laptop belonging to Mr. Siad. Police allege the mayor was "smoking narcotics" in the video.