Rob Ford's relationships are under scrutiny again after it was revealed that Toronto's mayor wrote letters of reference for two men convicted of crimes.
In the most recent case, Ford wrote a character reference for a man he described as his friend, Alessandro (Sandro) Lisi, who was recently arrested on drug-related charges and was previously convicted of threatening to kill his girlfriend.
CBC News has also learned Ford wrote a separate letter for Douglas Sedgewick, a tow truck operator with a criminal record including murder, as well as a recent conviction for "stunt driving." He was travelling nearly twice the speed limit in an unlicensed tow truck.
The letter for Lisi was made public in court on Tuesday. Lisi's most recent drug charges stemmed from a separate police investigation after the Project Traveller raids.
The letter Ford wrote was to assist Lisi at a sentencing hearing after he was convicted of making threats. Lisi is appealing the conviction.
Lisi is known as Ford's friend and occasional driver.
"I have known Mr. Alexander Lisi through his volunteer work on my 2010 election campaign," Ford wrote in the letter dated June 4, 2013. "Mr. Lisi was an exemplary member of my campaign team, where he displayed exceptional leadership skills and worked hard both in and out of the campaign office."
The letter concludes with: "I have known Mr. Lisi for several years and he has always conducted himself in a courteous and polite manner. I would be pleased to provide him with a reference."
When Lisi was charged with drug offences in early October, Ford described him as "a good guy and I don't throw my friends under the bus."
The mayor said that Lisi was on the "straight and narrow," and he had never seen him drink or use drugs.
"So, I'm surprised. I'm actually shocked," he said.
Separately, in early 2012, Ford wrote a character reference letter for Sedgewick, who had been denied a tow truck licence by the city.
On Nov. 11, 2011, a compliance officer had charged Sedgewick with operating a tow truck without a licence.
A week later, Sedgewick applied for a licence. City staff would learn that he had been convicted the previous year of driving nearly twice the posted limit while in his tow truck and also had received a seven-day driver's licence suspension in connection with that same incident.
His application was rejected.
Sedgewick then asked for a hearing before the Toronto Licensing Tribunal, which occurred on Jan. 26, 2012.
At the hearing, Sedgewick produced a letter from Ford, which was written on the mayor's letterhead.
In the letter, Ford said he knew Sedgewick through his role "as an elected official active in the community," saying that he believed the driver "always conducted himself in a courteous and polite manner."
While city lawyers had recommended denying a licence to Sedgewick, the tribunal decided to issue him one, on a probationary basis and under several conditions.
Sedgewick was ordered to provide an updated driver's abstract for the next three renewals of his licence and was required to report any traffic charges or convictions within three days.
Sedgewick's criminal history includes a second-degree murder conviction in 1982, for which he was fully paroled in 1992, according to National Parole Board documents. In 1994, he was convicted of one count of possessing a narcotic, and he violated his parole terms at least three times after that, the files show.
'Numerous letters for people that have broken the law'
Coun. Doug Ford said Tuesday that his brother has written letters on behalf of people who have "broken the law."
"Rob, over his term, being down at city hall for 14 years, he's written numerous letters for people that have broken the law," he said, referring to the mayor's years at city hall, including the decade he spent as a city councillor.
He went on to say that the mayor "doesn't judge people, he doesn't throw the book at them."
But two councillors said the mayor needs to be more discriminating in who he publicly backs.
Shown the letters of support, Coun. Michelle Berardinetti, a member of Ford's cabinet-like executive committee until last year, said: "That's not something that I would ever do. And it's inappropriate to be giving references to characters like that."
Fellow councillor Adam Vaughan said Ford should have stayed out of the Lisi matter. "You do not interfere as a politician with court proceedings, period," he said. "And you certainly don't do it with your letterhead."
Questions about Rob Ford’s associates first arose when he was photographed with four young men outside a home in the northwest part of the city. Some of the men were arrested and charged as a result of a major gang raid called Project Traveller in June, and one of them was shot dead.