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Canadian businessman and philanthropist Michael DeGroote is photographed in his hotel room in Toronto, Ontario, Canada. DeGroote, who suffers from chronic pain since he had a stroke five years ago, has spent a lot of money travelling all over the world looking for relief.Deborah Baic/The Globe and Mail

Michael DeGroote, the billionaire philanthropist who became ensnared in a bitter battle over the control of a gambling empire in the Dominican Republic, provided a violent criminal with $500,000 before that man began plotting, along with other members of organized crime, to involve themselves in the fight for the troubled Dream casino chain, according to a CBC News report.

In January, a joint Globe and Mail/CBC investigation detailed how Mr. DeGroote, 82, lent $112-million to the Dream Corporation, a company controlled by three Toronto-area men who had set their sights on launching a chain of casinos across the Caribbean. All three men – brothers Antonio and Francesco Carbone and Andrew Pajak – had ties to organized crime. When relations between the trio deteriorated and questions started being raised about what became of Mr. DeGroote's money, the trio's underworld associations began to percolate to the surface. Things turned violent in late 2013, when a bloody brawl at the company's Santo Domingo headquarters spilled out onto the street.

In all of his public statements on this controversy, Mr. DeGroote has said through a lawyer that he was not complicit in organized crime becoming involved in the dispute, and that his role in the affair was strictly as a lender whose investment went awry. But documents obtained by CBC and broadcast on Friday night show that Mr. DeGroote took a more active role at the height of the dispute than previously known. On Aug. 1, 2013, one of the billionaire's friends and business associates wired, at Mr. DeGroote's behest, $500,000 to a bank account controlled by Alex Visser, a con man with many aliases and dozens of criminal convictions, CBC reported. The man who wired the money to Mr. Visser, Ivan Cairns, declined to comment to a CBC journalist about the payment. But in an e-mail obtained by CBC, Mr. Cairns explained to a lawyer for the Carbones that the money was sent at "the request of Mr. DeGroote."

Two weeks after that money was transferred, Mr. Visser was captured on surveillance cameras touring a Dominican Dream casino with the late Vito Rizzuto, the godfather of the Montreal Mafia. In the months that followed, other members of Mr. Rizzuto's crime family arrived in the Dominican and took up roles at the casino company, declaring Mr. Pajak and themselves – and not the Carbone brothers – the rightful leaders of Dream Corporation.

Mr. DeGroote has consistently denied having "any association of any kind" with Mr. Rizzuto. Mr. DeGroote declined to respond to questions about the purpose of the wire transfer. Instead, he issued a statement that described his 14-year battle with chronic pain and how his high-dose drug regimen at times interferes with his "cognitive abilities."

"These drugs, coupled with his ongoing pain, do at times significantly interfere with Mr. DeGroote's cognitive abilities depending on the amount of emotional and physical stress that Mr. DeGroote is under at the time," said the statement, sent by Mr. DeGroote's lawyer, William McDowell.

Mr. DeGroote has launched a lawsuit against the Carbone brothers and Mr. Pajak, alleging that they misappropriated portions of his loan rather than investing the money in Dream. So far, the courts have consistently sided with Mr. DeGroote. Mr. Justice Frank Newbould declared in November, 2013, that Mr. DeGroote had "established a strong case in fraud."

But as part of that lawsuit, the octogenarian – who made his fortune in waste management and trucking – has had to answer questions, under oath, about his relationships with some of the unsavoury characters who involved themselves in the dispute.

During a 2013 cross examination, he was asked about a secretly recorded meeting he had with Mr. Visser, who had offered his services to Mr. DeGroote as someone who could gather evidence against the Carbone brothers. ("I am going to make sure that the Carbones can't even sell chestnuts on the corner of the … street," Mr. Visser said in the secretly recorded conversation on May 10, 2013.)

In the cross examination, Mr. DeGroote was asked repeatedly by a lawyer for the Carbone brothers about whether he had taken up Mr. Visser on his offer and hired him, something that Mr. DeGroote denied.

"I have not paid anything directly or indirectly for Mr. Visser," he said.

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