Toronto police detectives investigating Mayor Rob Ford recently obtained almost 10 gigabytes of data — mostly video and audio — recorded by Alexander “Sandro” Lisi’s iPhone, according to new search warrant documents filed in court.

Lisi, Ford’s friend and occasional driver, is believed by police to have made “surreptitious recordings” during what they call the “extortion time frame” connected to the crack video scandal. Police state they believe Lisi’s phone may provide evidence that others were involved in trying to retrieve the now infamous video, filmed a year ago while Ford was in the company of alleged gang members and in the basement of a known crack house in Etobicoke.

Lisi is a close friend of Ford and is facing extortion charges related to attempts to retrieve the embarassing video of Ford smoking crack and making racially charged and homophobic statements.

The “extortion time frame” referred to by the Project Brazen 2 police squad investigating Ford and others is roughly one month leading up to the day the Star and Gawker publicized the video’s existence on May 17, 2013, and one day after that. That was a period when Ford was dismissing reports of the video’s existence.

Police state in their application to access the phone data that they believe it will “further the investigation and potentially include or exclude” other people related to the extortion allegations. Detectives do not name those parties, but in the new search warrant application Ford is listed as the second “person of interest” in the investigation. Lisi is listed as number one.

Gaining access to the Lisi cellphone has taken five months. It was seized when Lisi was arrested in early October on drug trafficking charges. Police sealed the phone in an evidence bag inside a police storage locker while they waited for judicial approval to examine it. Once the request was approved, first with a search warrant related to Lisi’s drug charges, detectives realized they lacked the forensic capablity to access the phone, according to the new documents.

Police contacted Apple headquarters in California and were slotted in (Apple gets many of these requests, the Star has been told) for Feb. 13. Det. David LaValee of the Project Brazen 2 squad flew to California on Feb. 12 and went to see Apple’s “Law Enforcement Compliance Team” the next day. Apple retrieved between nine and 10 gigabytes of video and audio files recorded by the phone, the new search warrant documents state. LaValee flew home with the extracted data on an external hard drive he had brought with him. Detectives then realized that they needed to go back to court and obtain a new warrant, listing “extortion,” not drug trafficking, as the charge they were currently investigating.

“In an abundance of caution I am requesting a Criminal Code search warrant be granted in order to ensure a comprehensive and thorough analysis of the extracted data from Lisi’s cellular phone,” LaVallee wrote in a March 7 search warrant application, portions of which were made public Monday, while other parts of the document are still subject to a publication ban.

According to the application, detectives did not view the new data before receiving court permission.

Detectives state that Lisi made secret recordings of people connected to the crack video to “prove he was able to retrieve” it. Police are also trying to learn who Lisi was talking to and texting, and what they were discussing.

The two victims of Lisi’s alleged extortion attempt were Mohamed Siad (who filmed the video and tried to sell it to the Star and Gawker.com) and Liban Syad, an associate of Siad. Both were arrested in the Project Traveller guns and drug raids last year.

In outlining their case to the judge, detectives say their interviews had turned up “numerous instances of Robert Ford exhibiting bad behaviour both during work hours and during his personal time.” Detectives say this “behaviour included substance abuse, drinking and driving, physical altercations with staff members and a friendship with a man who staff members knew as “Sandro” who was believed to be involved in drugs.”

Kevin Donovan can be reached at (416) 312-3503 or kdonovan@thestar.ca