Accused crack video extortionist Alexander “Sandro” Lisi once threatened an 18-year-old woman by motioning that he would slit her throat, allegedly menaced a second woman by saying he would have acid thrown in her face, and was driving in a car crash that critically injured an elderly woman pedestrian, according to newly obtained court documents. Most recently, he was convicted in 2013 of threatening to kill a woman.

Those court documents and an ongoing Toronto Star investigation reveal that Lisi — the man Mayor Rob Ford spoke up for on City of Toronto letterhead and touted as “straight as an arrow” — has a long history of threatening violence against women and a penchant for dirty tricks. Among those tricks, he boasts that he infests his enemy’s homes with bedbugs and has people call police on his behalf to inform on rival drug dealers.

Lisi’s lawyer, Seth Weinstein, on Tuesday wrote to the Star saying his client was not interested in talking to the newspaper.

“Mr. Lisi is not a public figure and, as such, he will not be baited into a discussion of his personal life with you or any member of the media,” Weinstein wrote in an email that dismissed much of the Star’s research as “unworthy of responsible journalism.”

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The relationship between Ford and Lisi, his occasional driver, is central to the Project Brazen 2 investigation being carried out by Toronto police. Detectives had both men under surveillance last summer as they met in parks, schoolyards and at Lisi’s home. Ford has criticized police for expending what he has described as “millions of dollars” on what he deems a waste of time. Project Brazen 2 detectives have charged Lisi with trafficking marijuana, and with extortion over an attempt to retrieve the video showing Ford smoking crack cocaine and making racially charged and homophobic remarks. None of these allegations against Lisi has been tested in court.

Wednesday, lawyers for the Star and other media will be in front of a judge, seeking access to search-warrant information filed by police in an attempt to retrieve video, audio and text messages from Lisi’s iPhone, his iCloud storage and from other devices connected to the investigation. Police believe Lisi recorded his interactions with Ford over the past year, sources say. Detectives are trying to determine whether someone asked Lisi to retrieve the crack video.

So close is the relationship between Ford, 44, and Lisi, 35, that Ford entrusted Lisi to watch over Ford’s 8-year-old daughter at a day-long Chinese gala in Richmond Hill in late 2012 or early 2013, according to statements contained in a police document used to obtain a search warrant.

“Sandro looked after her that day,” according to a Ford staffer who provided the information to police. The police documents also note that Lisi drove Ford, his daughter and his 5-year-old son to the black-tie Garrison Military Ball in February 2013, from which Ford was urged to leave because he appeared impaired.

Also in the vehicle with the Ford children was Ford friend Bruno Bellissimo, referred to in the search warrant documents as a “self-admitted crack user.” Bellissimo was charged two weeks after the ball with with assaulting his parents and threatening to kill his mother — charges for which he was later convicted.

Ford has said little in public about his relationship with Lisi, which has included trips together to Toronto Maple Leafs games.

The mayor wrote a letter on Lisi’s behalf last year, when Lisi was being sentenced for threatening to kill a woman. In the letter, Ford said Lisi was part of his 2010 mayoralty campaign and “worked hard both in and out of the campaign office.”

Ford was last seen with Lisi at the Steak Queen restaurant in Etobicoke, the night the mayor was recorded speaking in a Jamaican patois and calling Police Chief Bill Blair a “----sucker.”

Lisi has been in and out of the court system his entire adult life. He is well known to police as a low-level drug dealer in the north part of Etobicoke, an area that includes the Dixon community that was the focus of the Project Traveller drug and gun raids last year. Lisi lives in his parents’ basement, just east of the Dixon community. His father works as a contractor and his mother is an administrator at a retirement home.

During one court appearance, Lisi said he was raised in a “loving and close-knit family” that includes a younger sister.

Lisi attended Richview High School in Etobicoke and dropped out in Grade 11. He took several courses the next year at Scarlett Heights, including a parenting course. The yearbook includes a photo of Lisi posing with a doll used for parenting instruction.

Court records show that since high school, Lisi has been charged at least six times with drug possession. All but one charge was withdrawn by a Crown attorney, though his co-accused was convicted in one case, fuelling speculation in Etobicoke that he was a police informant. The Star has been told by police that Lisi was never a registered police informant.

A 2012 assessment report prepared on Lisi by the Vitanova Foundation attributes many of his problems to his poor “management of anger” and notes that he “appears to choose female companions who are not compatible.”

A Crown attorney involved in his most recent case commented on Lisi’s history of “criminal harassments and threatening,” and noted that Lisi appeared not to have any fear of people in authority being involved.

In a case from 2001, Lisi was convicted of criminal harassment and threatening after a young woman he was interested in complained to police (along with her parents) that Lisi was stalking her.

Among the threats to the woman were, “I’m going to break your legs, you ----ing bitch” and one to the woman’s father: “As soon as you leave your building a 45 gun is pointing at you. I’ll let you leave this time, but next time we won’t let you leave,” according to court records in the case. Lisi was sentenced to 15 days in jail and three years’ probation.

The next year, 2002, Lisi stalked an 18-year-old student at a Toronto high school. Then 24, Lisi went into her class, made eye contact and “made a motion with his finger across his neck, indicating a cutting of a throat type of gesture,” the prosecutor told the court. Later, Lisi punched the young woman in the eye.

Another time, Lisi, who appeared to be watching her from a distance, called her cellphone and threatened to stab a friend she was walking with.

Lisi was convicted of threatening, assault and criminal harassment. He was sentenced to 90 days in jail, on top of 45 days he had spent in pre-trial custody.

Lisi pleaded guilty to the charges in both cases.

In 2007, Lisi was charged with assault, uttering death threats and criminal harassment related to complaints from a former girlfriend who said Lisi was stalking her. Lisi is alleged to have punched her while they were driving in the car, bitten her arms, and threatened that he would have acid thrown in her face. He told her “he was going to stab her to death because she was a whore,” according to allegations by the prosecutor presented at Lisi’s bail hearing.

Lisi was given bail after a hearing in which three people testified that Lisi was a person of good character.

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The case wound its way slowly through court and there were delays, one of them because the female complainant began a relationship with another man, became pregnant and asked for a delay of proceedings until after the birth of the child.

The Crown withdrew the charges, with consent of the judge — who told the court, “Mr. Lisi, sometimes things happen and the State couldn’t provide you with a date earlier.” Lisi signed a peace bond and was warned by the judge to stay away from the complainant.

Weinstein, Lisi’s current lawyer, told the Star there was no “admission of the allegations” by Lisi in that case.

In Lisi’s most recent case, in which he was charged with threatening to kill a woman in 2011, he was sentenced in 2013 to two years’ probation and a five-year weapons ban. Lisi was also ordered to attend an anger-management program. The judge in the case acknowledged that the victim was frightened of Lisi and noted the “controlling, manipulative relationship” he had with her.

That is the case for which Ford provided a Lisi with a character reference on Mayor of Toronto stationery.

Ford and Lisi were introduced by Payman Abdoodowleh, a football player two years older than Lisi who knew him from the neighbourhood. Abdoodowleh, who has a criminal record for assaulting his brother and a police officer, on separate occasions, went on to help Ford coach the Don Bosco high school football team.

Just out of their teen years, the exploits of Abdoodowleh and Lisi were legendary in Rexdale, the north part of Etobicoke.

In later years, according to sources that include former drug clients and rival drug dealers, Lisi was known for paying people with drugs to call police anonymously and “rat out” his rivals, giving rise to his nickname, “the Rat.”

Two men the Star interviewed said Lisi has shown them a small vial of bedbugs that he boasted he picked up in downtown Toronto and carries around to threaten his enemies. In one case, a family was infested by bedbugs after a visit by Lisi, according to an interview with a member of the family.

Lisi lawyer Weinstein called this information “unsubstantiated hearsay in which no charges have never been laid and no proceedings have ever been commenced.”

One story that has gone around about Lisi is that he was responsible for the death of an elderly woman. Records filed in civil court reveal he was involved in a serious vehicle incident when he was young.

On a cold, dry afternoon in November 1999, a then 21-year-old Lisi was driving south on Islington Ave. near Eglinton Ave. when he struck 76-year-old Kupraty, who was crossing the road.

Kupraty was crossing the intersection of La Rose Ave. near her home, where there was no crosswalk, when, according to statements given to police by Lisi and three high school friends (who were in a nearby car), another driver in the right lane slowed down to allow her to pass.

Lisi, according to his statement and the witnesses, pulled out from behind that car and passed it on the left, striking Kupraty. Witnesses described her flying and spinning through the air after making contact with Lisi’s windshield. Police were never able to locate the other car.

“I can see her in my head — laying on the ground,” one witness told a police officer, who recorded it in his notes. “I can’t believe she’s alive. I thought she was dead.”

Lisi initially told the police officer who took his statement that he was driving 60 to 65 km/h in a posted 60 km/h zone. After reviewing his statement, he asked the officer to amend it to say he was driving 55 to 65 km/h.

According to police notes from the scene, filed as part of a civil case, Lisi was arrested and taken to a police station in handcuffs. Criminal charges were never laid.

Kupraty was rushed to Sunnybrook Hospital, where she remained in a coma for at least three months. She suffered severe head trauma and a brain injury. She also had facial and clavicle fractures resulting in permanent disability, according to medical records filed as part of the claim.

After five months in hospital, she was transferred to a Toronto rehabilitation facility, where she remained dependent for all of her daily needs and had limited cognitive functions, a report noted.

Kupraty died on July 26, 2003.

According to a statement Lisi made to police, his driver’s licence had been suspended two to three months prior to the collision, though the reason for the suspension is unclear. He was in the process of retesting for his G-class licence and told a police officer he had been issued a temporary licence days before the accident. That day, Lisi was driving a rented Buick LeSabre.

“We had heard then that he had already a lousy driving record, but there was nothing else we could do,” said son Jerry Kupraty in an interview.

The Kupraty family sued the company that insured the car Lisi was driving. In the civil documents that outline the settlement of the case, the Kupraty family acknowledged some shared responsibility, though they believe Lisi was “at fault.” The Kupratys settled out of court and received a payment of $121,000 from the insurance company.

Lisi has had two accidents since then, including one in 2010 in which he sued two women for $1 million, claiming he was rear-ended and has suffered “post traumatic insomnia.” He told a court-appointed assessor as part of his recent criminal conviction that he received a financial payout when that case was settled. He was involved in another accident in February 2013 and told the assessment clinic that he now suffers from vertigo as a result.

Lisi and Ford remain close, and it does not appear that Lisi is cooperating with the police investigation.

When Lisi was arrested and charged with drug trafficking last fall, Ford was asked by reporters about his friend. “He’s a good guy,” Ford told reporters. “I don’t throw my friends under the bus.”

With files from Jesse McLean and Jayme Poisson