10/22/2013 01:27 EDT | Updated 01/23/2014 06:58 EST

Rob Ford wrote letters of support for Lisi, Sedgewick

Rob Ford’s relationships are under scrutiny again after it was revealed that the mayor wrote two letters of reference for men convicted of crimes.

Questions of Ford’s associations 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.

In this 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 convicted of uttering threats. CBC News also learned Ford wrote a separate letter for Douglas Sedgewick, a tow truck operator with a conviction of going nearly twice the speed limit in an unlicensed tow truck.

The letter for Lisi was released in court on Tuesday. Lisi’s most recent drug charges stemmed from a separate police investigation after the Project Traveller raid.

The letter was to assist in Lisi's sentencing regarding his conviction for threats.

Lisi is known as Ford’s occasional driver and “friend”.

“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 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 first charged with drug offenses in early October, Ford said Lisi was "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.

A year earlier, Ford wrote a character reference letter for a tow-truck driver with a criminal record who has been convicted of speeding in his commercial vehicle.

On Nov. 11, 2011, a compliance officer charged Sedgewick with operating a tow truck without a licence.

A week later, Sedgewick reapplied for a licence, though 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 at the Toronto Licensing Tribunal, which occurred on Jan. 26, 2012, so that it could determine whether he could have a licence.

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 counsel had called for 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 he is required to report any traffic charges or convictions within three days.