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Spiros Papathanasakis, middle, walks with associates outside Toronto city councillor Gary Crawford's campaign office on Sept. 18, 2022.Christopher Katsarov/The Globe and Mail

A key figure in several public-sector scandals in Ontario who has touted his ability to influence the awarding of multimillion-dollar government contracts has re-emerged in Toronto’s municipal election, forging close ties with the politician who has presided over the city’s $15-billion operating budget.

Spiros Papathanasakis, who was the subject of a 2018 Globe and Mail investigation that chronicled his previously unknown role in governance crises at Canada’s largest school board and a Toronto hospital, has involved himself in the re-election campaign of three-term Toronto councillor Gary Crawford.

Mr. Papathanasakis has been filmed and photographed at several recent campaign events with Mr. Crawford. These include photos of the two men conversing at a political fundraiser in April, footage of Mr. Papathanasakis volunteering in Mr. Crawford’s campaign office and photographs of Mr. Papathanasakis at one of Mr. Crawford’s campaign events. Mr. Crawford has also hired, as his top political aide, Monique Lisi, a long-time business partner of Mr. Papathanasakis who has been involved with him in at least five ventures.

Mr. Crawford, top, leaves his campaign office at the Sept. 18 event, which Mayor John Tory, bottom, also attended.Christopher Katsarov/The Globe and Mail

A close ally of Mayor John Tory, Mr. Crawford has been the city’s budget chief for the past eight years. The former Toronto District School Board trustee has been a councillor in the city’s east-end suburb of Scarborough since 2010.

In a statement, Mr. Crawford said Mr. Papathanasakis “holds no official role on my campaign,” but declined to explain what he has been doing with him on the campaign trail.

When Mr. Crawford launched his re-election bid on Sept. 10, Mr. Papathanasakis and his son were filmed at the campaign office event by a news outlet. In the footage, Mr. Papathanasakis is seen inside the campaign office with Mr. Crawford, as well as outside in the parking lot, chatting with volunteers. Mr. Papathanasakis’s son was filmed holding clipboards used by Mr. Crawford’s canvassers.

A week later, on Sept. 18, Mr. Papathanasakis was back at the campaign office for a speech by Mr. Tory. On that day, the incumbent mayor appeared in Scarborough – where he shares office space with Mr. Crawford – and Mr. Papathanasakis was photographed entering and leaving the premises by a Globe photographer.

When The Globe’s photographer took pictures of Mr. Papathanasakis crossing the parking lot outside the office, a man accompanying Mr. Papathanasakis demanded that the images be deleted. When the photographer refused, the man, who declined to identify himself, warned him to “expect new experiences.”

Mr. Crawford did not address questions about the identity of the man who made the perceived threat. The Globe e-mailed an image of the individual to Mr. Tory’s campaign, and spokesperson Jenessa Crognali said no one on the team knew him.

As for Mr. Papathanasakis, Ms. Crognali said he “is in no way involved with the John Tory re-election campaign.”

The man at middle, standing with Mr. Papathanasakis, confronted The Globe and Mail's photographer on Sept. 18 and demanded he delete his photos.Christopher Katsarov/The Globe and Mail

Mr. Crawford’s ties to Mr. Papathanasakis run deeper than the current election campaign.

In 2019, Mr. Crawford hired Ms. Lisi to work in his council office, and she was promoted to chief of staff the next year. Ms. Lisi has moved in near lockstep with Mr. Papathanasakis in business ventures that include development of a cancer drug and a private school. She has also been involved with him in public institutions in the Toronto area over the past two decades – including stints that ended in governance chaos.

The Globe’s 2018 investigation into Mr. Papathanasakis detailed his role behind the scenes in several public-sector scandals dating back more than 20 years:

  • In 1998, Mr. Papathanasakis helped orchestrate a coup that resulted in the board of directors of Toronto East General Hospital being replaced by a new board, one that would eventually include his brother and a number of his family friends. Not long after, Mr. Papathanasakis and Ms. Lisi were given jobs at the hospital. Soon, the hospital’s governance became dysfunctional and the hospital was placed under control of a supervisor. A 2002 investigation ordered by the province’s health minister concluded a “local political machine” had seized control of the hospital and that Mr. Papathanasakis “openly and freely admits his control of the board.”
  • In 2009, after the husband of Caledon’s then mayor, Marolyn Morrison, was threatened by an organized-crime figure over a proposed housing development, and later ambushed and assaulted in his driveway, Mr. Papathanasakis got involved. He contacted a friend of Ms. Morrison, and urged her to set up a private, one-on-one meeting between himself and the mayor, explaining he was “well versed in the street.” His overtures were unsuccessful, and Ms. Morrison and her friend made complaints to police.
  • Between 2010 and 2014, Mr. Papathanasakis exercised influence at the Toronto District School Board despite having no official role there. In 2011, he and Ms. Lisi accompanied, at their own expense, an official delegation of the TDSB on a student recruitment trip to China, and no one from the board has explained why they were included. A number of Mr. Papathanasakis’s close associates and family members secured high-profile TDSB jobs during this period, while other associates benefitted from school board contracts – such as a $1.2-billion deal to outfit school roofs with solar panels.
  • In 2016, Mr. Papathanasakis became embroiled in a lawsuit with John Aquino, who was then the president of Bondfield Construction Co. Ltd. At the time, Bondfield was one of the largest builders of public works in Ontario. During an examination by one of Mr. Aquino’s lawyers, Mr. Papathanasakis explained how he first got involved in business with Mr. Aquino: “John wanted to win Infrastructure Ontario jobs and he knew I was doing a good job of it, and by knowing me, he thought he’d get to know some people and win.” He provided no evidence of how he helped Mr. Aquino or what he could do for him.

Monique Lisi listens to Mr. Crawford at a campaign event.Climate Channel/YouTube

In his response to The Globe, Mr. Crawford said he was unaware that Ms. Lisi was involved in some of these controversies when he hired her in 2019. Ms. Lisi was a candidate for trustee of the TDSB in the 2010 municipal election, and co-campaigned with Mr. Crawford, who was first elected as councillor that year. Mr. Crawford praised Ms. Lisi as a “professional and skilled” staff member, but said that, “out of an abundance of caution,” he was going to schedule a meeting with an independent third party from the City of Toronto to review The Globe’s questions about her history. He declined to elaborate on the identity of this third party. When asked to provide more detail, Mr. Crawford declined, citing privacy policies governing what can be said about city employees.

In an e-mailed statement, Ms. Lisi said The Globe’s understanding of her professional past – which she described as inaccurate – had no bearing on her work for Mr. Crawford.

Mr. Papathanasakis did not respond to questions sent to him via Ms. Lisi and two of his lawyers. In answers Mr. Papathanasakis provided to The Globe in response to a story in 2014, he said, “I understand the value and importance of good relationships. My relationships have served both my charitable endeavours and my business endeavours.” He later sued The Globe over that article.

Mr. Crawford speaks at a campaign event as Mr. Papathanasakis walks past behind him.Climate Channel/YouTube

Since The Globe’s investigation was published in 2018, Mr. Papathanasakis has continued to find himself mired in conflict at the intersection of business and politics.

In 2020, a Toronto lighting company sued Mr. Papathanasakis, Ms. Lisi and a registered lobbyist, Raj Rasalingam, alleging the trio made negligent representations about Mr. Rasalingam’s ability to secure retail cannabis licences from the government of Ontario in 2018. The lighting company, Etlin-Daniels, alleged it paid Mr. Rasalingam a $750,000 retainer shortly before learning that the government was imposing a lottery, not an application system, for granting such licences, which eliminated any advantage a lobbyist might possess. When the company demanded its money back, it received no response, it alleged in its claim.

Ms. Lisi has since been dropped as a defendant in the lawsuit. In a brief interview with The Globe in May, Ms. Lisi said that when Etlin-Daniels initially sued, it cast “a large net,” which was the only reason she was named at the outset. She said she performed communications work for Etlin-Daniels.

David Daniels, president of the lighting company, said in a May 12 e-mail that he would prefer not to speak about the case while it is before the courts. He followed up in an Oct. 5 e-mail, asking The Globe not to name Ms. Lisi because she is no longer a defendant.

The company’s claim against Mr. Papathanasakis was automatically stayed in 2021 when he sought bankruptcy protection. In his bankruptcy filings, he listed $1-million in liabilities, with his largest debt identified as $800,000 owed to the law firm representing Etlin-Daniels. The filing lists a $20,000 Maserati as his only asset.

For his part, Mr. Rasalingam declined to explain how Mr. Papathanasakis became wrapped up in the dispute, except for an e-mailed statement from his lawyer, saying: “Our client does not have a relationship with Mr. Papathanaskis.”

Marolyn Morrison, shown in 2018, is the former mayor of Caledon, Ont.Glenn Lowson/The Globe and Mail

Ms. Morrison, who was the mayor of rural Caledon, Ont., for 11 years, said she was baffled by Mr. Crawford’s decision to associate with Mr. Papathanasakis.

When Ms. Morrison first heard of Mr. Papathanasakis, it was 2009, she was still mayor and she felt under siege from developers seeking to expand Caledon’s housing footprint. The previous year, her husband, John Morrison, had been approached by a man with ties to organized crime, Vladimir Vranic, who threatened him and demanded that he press his wife to approve a proposed development. Ten days later, Mr. Morrison was ambushed and assaulted in his driveway by an assailant who has never been identified.

In September, 2009, Mr. Papathanasakis inserted himself into the matter by trying to persuade one of Ms. Morrison’s friends to set up a private, one-on-one meeting so he could lobby the mayor about a proposed housing development. The friend, Nancy Koehle, later complained to police about Mr. Papathanasakis’s phone calls, as did Ms. Morrison. Ms. Koehle told the police that Mr. Papathanasakis said to her: “I know how to make these things go away.”

In an e-mailed statement, Ms. Morrison said she has no idea why “any politician would get involved with Spiros Papathanasakis or have any affiliation with him.”