Toronto City Servant’s Double Life: Senior Director of Traffic Services or Criminal Syndicate Player?


He was known as a long-serving loyal servant of Toronto’s city council. Kypros Perikleous, the 55-year-old veteran of city service, spent nearly four decades maneuvering the halls of political power. In a career that spanned 37 years, Perikleous rose to serve as a senior director of transportation services – a position he relinquished due to heart condition which triggered a period of long-term medical leave lasting until his retirement in December last year.

But beneath the veneer of a public servant strictly adhering to the letter of the law, runs a narrative that paints Perikleous in a drastically different and darker light. This alternative narrative paints him as a member of the Greek Syndicate, a notorious criminal organization in the Greater Toronto Area, according to the Royal Canadian Mounted Police (RCMP).

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Allegedly, it was during his time earning an honest living at the city council that Perikleous was secretly extending his influence into the ignoble world of illegal bookmaking, his actions clandestinely aimed at further empowering the Greek Syndicate. In addition, he also faces charges for the possession of proceeds of crime amounting to over $5,000 and for inappropriate storage of a firearm.

The law enforcement agency, known as the Mounties, espouse the belief that Perikleous played a role of dire importance – one that brought him close to the central power base of the criminal enterprise; a proximity that led to him being slapped with charges of involvement with a criminal organization.

Brian Greenspan, Perikleous’ legal representative, has steadfastly refuted all allegations, and vows to contest each one in court, emphasizing his client’s innocence. He further underscores that the contested firearms were not only licensed but were also stored within the boundaries of published guidelines laid down by the RCMP.

Perikleous wields the ignominious honor of being among the 16 individuals corralled in a law enforcement sweep in April across multiple properties in Toronto, Scarborough, and Vaughan. This raid led to a significant confiscation of firearms, illegal gaming devices, jewelry and over $250,000 in cash.

The authorities suspect Paris Christofouro, a former Hells Angels enforcer, to be the mastermind presiding over the criminal network. A man who is no stranger to crime, Christofouro was sentenced to a hefty nine-year prison term in 2006 for an attempted shooting which tragically disabled an innocent passerby. Since evading consecutive attempts on his life in 2018 and 2017 respectively, Christofouro has remained off-the-grid, his whereabouts a mystery.

As the revelatory charges against Perikleous come to light, there lingers an unsettling sense of disbelief, especially among those who’ve formerly worked with him like Mary-Margaret McMahon, a former city councilor who described him as “super friendly, earnest, hardworking, and keen to find solutions to help build a better city”. The shocking news can hardly match up to their memories of Perikleous, known affectionately as “Kyp”, who now stands on the precipice of potential convictions that could result in up to seven years imprisonment.