He is a formidable political organizer, the owner of a pub, a cancer drug research firm and a professional soccer club in Greece. Among his closest allies are former provincial ministers, city councillors and school board trustees.

And now Spiros Papathanasakis is running to become a school trustee – though many who know him say he already has significant sway over the affairs of Canada's largest school board.

His deep connections within the board were on display earlier this year, when trustees and senior staff piled into the Marquis of Granby, a downtown pub. They were greeted by Chris Bolton, their host and the board's chair at the time. Mr. Bolton worked the private, second-floor room in his silky red Chinese jacket, which he wore to mark the beginning of the Lunar New Year. Mr. Papathanasakis, the owner of the Church Street pub, mingled with guests, while drinks flowed.

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At first glance, the pair is an odd coalition: Mr. Bolton is a left-leaning, soft-spoken Sinophile and Mr. Papathanasakis is a street-smart businessman and inner-city youth advocate whose pub caters to fans of mixed martial arts.

But during Mr. Bolton's decade-long tenure at the school board – before he abruptly resigned in June – Mr. Papathanasakis became inextricably linked to Mr. Bolton, a handful of other trustees and several of the board's highest-ranking staffers.

The 58-year-old businessman has no official role at the school board, but that has not prevented him from inserting himself into board business, 10 former and current board officials explained in interviews.

He usually met Mr. Bolton weekly for coffee and frequently spoke to trustee Sheila Ward, sources said. He has intervened in a major food-services dispute and he once joined Mr. Bolton and senior staff for part of an official TDSB trip to China for reasons that no one from the board has been willing to explain.

The fact that there is such a lack of transparency and no explanation as to why Mr. Papathanasakis has been able to involve himself in board business is symptomatic of the dysfunction and lack of proper governance at the school board. A forensic audit by Ernst & Young LLP described a "culture of fear," where staff feel pressure by trustees not to follow policies and worry about losing their jobs if they disobey orders.

And although most of his interactions with the school board have been in the background, Mr. Papathanasakis now wants a seat at the table.

He is running to become one of 22 trustees in Monday's municipal elections. His campaign in Ward 4 – a catchment north of Highway 401 that includes the Jane and Finch neighbourhood – is heavily resourced and well organized, his rivals said. "It's like he's running for mayor," said Anthony Perruzza, one of the incumbent councillors for the area.

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The ward is far from Mr. Papathanasakis's roots in Cabbagetown, where he runs the Cabbagetown Youth Centre. The centre's arts, music and sports programs for at-risk youth have received $3.2-million in funding over the past five years from the school board. His 40 years of working with children have garnered him a cadre of prominent and vocal supporters."I think of Spiros as an angel," said former Ontario cabinet minister George Smitherman.

Mr. Papathanasakis says there's a much simpler explanation.

"I understand the value and importance of good relationships," he said in an e-mail response to The Globe and Mail. "My relationships have served both my charitable endeavours and my business endeavours."

One former trustee described having to "kiss the ring" to obtain Mr. Papathanasakis's support for a particular initiative that was due to come before the board. Another high-ranking TDSB official described him as "the big fish" behind the trustees.

Kristyn Wong-Tam, the councillor for the downtown ward where Mr. Papathanasakis's pub is located, was one of the only public officials, former or current, contacted by The Globe who agreed to speak on the record about what she called his "sphere of influence."

When Ms. Wong-Tam successfully ran for election in 2010, she said Mr. Bolton urged her to meet Mr. Papathanasakis, a man she had never heard of, to seek his support. He was described as a kingmaker, she said. (Mr. Papathanasakis backed an ally of Mr. Smitherman instead, she said.)

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"For reasons unknown to me, he seems to have been given a lot of power by those wielding real political power," Ms. Wong-Tam said.

And nowhere has that power been exercised more than at the school board.

The late bid

Late on a Friday afternoon in June, 2009, Mr. Papathanasakis showed up at the school board's third-floor purchasing and procurement department.

Mr. Papathanasakis was there to advocate on behalf of George Tsiopoulos, owner of food-services company Neo City Café and a supplier to Cabbagetown Youth, whose bid on a five-year cafeteria-services contract had been rejected that same day. Mr. Papathanasakis met with department head James Scott, according to sources close to the situation.

There was nothing Mr. Scott could do because the time stamp clearly showed that the bid was late. Mr. Tsiopoulos' wife, Stella, had arrived at the TDSB's purchasing department just minutes after the 4 p.m. deadline for bids.

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Mr. Bolton and Donna Quan, director of education, intervened on his behalf, according to the sources and internal e-mails obtained by The Globe.

Mr. Tsiopoulos, who declined to be interviewed, sued the TDSB in August, 2009, over its refusal to accept his bid. Neo City also has a lease at Yorkdale Secondary School and Mr. Tsiopoulos was trying to renew a second food-services lease at John Polanyi Collegiate Institute, which expired in July, 2012.

Mr. Bolton wrote an e-mail dated May 17, 2012, to a senior manager regarding the lease at John Polanyi and Mr. Tsiopoulos's lawsuit. "Do you know that you are exacerbating the difficult situation with this?" he wrote. "I would suggest that you take over the file and do this right."

Mr. Tsiopoulos did not succeed in renewing the lease. But a year later – days before the trial into his lawsuit over the late bid was set to begin – Ms. Quan told senior staff that Neo City Café would be submitting invoices totalling more than $200,000 that she said had never been paid.

Mr. Papathanasakis said in his e-mailed response that Mr. Tsiopoulos told him the nonpayment of the invoices, dating back three years, was "pay back" for his lawsuit. "I know that he was frustrated," he said.

The Neo City invoices did not come from purchasing, which is responsible for all invoices, and its staff had no involvement in the negotiations with Mr. Tsiopoulos, the sources said. The invoices came from Focus on Youth, a TDSB employment program for at-risk youth run by Jim Spyropoulos, an executive superintendent and protégé of Mr. Papathanasakis. They were not accompanied by supporting documents.

Mr. Tsiopoulos received payment for the invoices in $200,000 in June, 2013 as part of an out-of-court settlement with the TDSB.

The trip to China

Neo City was not the only time that Ms. Quan became involved in an issue near and dear to Mr. Papathanasakis.

In March, 2011, an official school board delegation flew to Beijing to recruit students from China to study at public schools in Toronto. The group included Mr. Bolton and Mr. Quan, then associate director of education. At some point during the trip they were joined by Mr. Papathanasakis.

Neither Mr. Papathanasakis, Mr. Bolton nor Ms. Quan have explained how it came to be that someone with no role at the school board joined the delegation. Mr. Papathanasakis attended some official meetings, according to a former school board official who spoke on the condition of anonymity.

In response to questions from The Globe, Ms. Quan provided a one-sentence statement that said Mr. Papathanasakis "did not serve the TDSB in any capacity." Mr. Papathanasakis would only say the purpose of his trip "was to visit a friend."

About two months after the group returned from China, a numbered company controlled by Mr. Papathanasakis purchased an unused school in Port Hope, Ont, land-title documents show.

The Pine Academy opened its doors in the fall of 2012 with the aim of drawing students from China, two staffers and one student from the school said. Its three owners were Mr. Papathanasakis, his business partner Monique Lisi and Wally Quan, a brother of Donna Quan, the senior TDSB staffer who helped lead the student recruitment drive in Beijing.

Mr. Quan, the owner of several appliance stores in Southern Ontario, did not respond to a list of questions about how he became involved in the private school. Mr. Papathanasakis said that he was introduced to Ms. Quan's brother by a "lawyer friend." Donna Quan visited the school in 2012 for a tour, one former Pine Academy teacher said.

Mr. Papathanasakis said Ms. Quan's brother owns real estate close to the school. "Since I wasn't able to be physically present at the school, Wally's presence and experience managing properties seemed like a good fit," he said.

Pine Academy's principal, Rudy Maharaj, took at least one trip during the 2012-2013 academic year to China in an attempt to recruit students, two former Pine staffers and one student said in interviews.

Ultimately, the school was unable to attract any students from China. Only five students attended the school and it shut its doors some time in 2013.

"Along the way we discovered that we really didn't have the resources to grow this business," Mr. Papathanasakis said in his e-mail response, adding that the property is up for sale.

The Marquis

If there is a single aspect of Mr. Papathanasakis's life that best represents his web of interests it is his Church Street pub.

The Marquis has been used to host a party not just for Mr. Bolton, but for Friends of Community Schools, the charity he founded. Currently, the pub's third floor is serving as campaign headquarters for Megan McIver, Ms. Wong-Tam's chief rival in the Ward 27 council race.

But how Mr. Papathanasakis came to finance the purchase of the bar suggests that, if he is elected trustee, he may have to declare at least one potential conflict of interest when it comes time to vote on major construction projects.

Mr. Papathanasakis purchased the bar on Oct. 1, 2012, for $2.05-million, according to land-registry records. He is the sole officer of a numbered company that made the purchase, which was financed in part with a $1.3-million loan from the Italian Canadian Savings & Credit Union Ltd.

One of the guarantors for that loan was John Aquino, the vice-president and general manager of Bondfield Construction Co. Ltd., a major builder of new schools. Most recently, Bondfield was awarded contracts totalling $11.6-million for additions to two TDSB schools.

Michael Solano, an executive with two Bondfield affiliates, Forma-Con and BMC Masonry, is also an investor in the Church Street building that houses the bar but not involved in the business, Mr. Aquino said in an e-mail.

Bondfield is a major donor to the Cabbagetown Youth Centre, and it is through the youth centre that he got to know Mr. Papathanasakis, Mr. Aquino said.

Mr. Papathanasakis said it's not surprising that some of his interests in his various endeavours overlap.

"Chris Bolton lives down the street from my bar; yes, I have financial partners; yes, we also tap them when fundraising."

With files from Stephanie Chambers