Gambling

Toronto Illegal Gambling Investigation: “Sad Day for Policing”

Posted on: February 5, 2026, 10:43h. 

Last updated on: February 5, 2026, 10:49h.

  • Seven Toronto police officers and one retired officer charged
  • “Project South” investigation expanded from charges of extortion over illegal gambling into accusations of drug trafficking, robbery, bribery
  • Police officers allegedly worked with organized crime figures 

An ongoing police investigation into an illegal gambling ring, involving organized crime figures, with allegations of extortion, has expanded to a jaw-dropping level, leading to the arrest of seven Toronto police officers, from a number of different divisions, and one retired police officer.

Seven Toronto police officers and one retired police officer have been arrested in a large-scale investigation into organized crime and corruption, that includes illegal gambling. (Image: Andrew Francis Wallace/Toronto Star via Getty Images)

Those Toronto cops, among 27 people who were charged, are accused of auto theft, drug trafficking (including illegal cannabis dispensaries, fentanyl, heroin and cocaine), robbery, bribery, firearms offences, shoot-ups of a police officer’s home, extortion and conspiracy to commit murder. It’s one of the largest cases of police corruption in Toronto history.

Organized Crime Involvement

In what’s seemingly right out of an episode of The Sopranos, the officers are accused of leaking addresses and inside police information to the “highest bidders” including hit men, leading to criminal acts, as well as leaking police officer addresses. There was an alleged conspiracy to kill a unit commander at Toronto South Detention Centre, according to York Regional Police in a news conference this morning.

The police investigation, called “Project South”, was launched in June 2025, and was executed across the Greater Toronto Area. In the news conference this morning, videos of shootouts in residential neighbourhoods were played, as well as an attempt by masked men to ram a police officer’s cruiser, an officer who was involved in the investigation, in the driveway of his home.

Hit Men Shooting Up Neighbourhood Homes

“This is shocking,” said Jim MacSween, York Regional Police Chief. “Corruption has no place in policing. There can be no stone unturned in this investigation.”

The investigation is ongoing and will continue “for some time”, added Ryan Hogan, York Regional Police Deputy Chief, calling it, “one of the most complex and challenging investigations of my 28-year career.

As we continue to investigate retroactively, we continue to examinate the relationships of the officers and how they connected to organized crime figures,” he said. “That investigation is ongoing. Organized crime is insidious, that takes place in many institutions, including policing.”

Illegal Gambling Racket Where People Were Extorted

Chief MacSween added that hundreds of police were involved in the investigations.

“We recognize these types of allegations shake the very foundation of trust that people place in the institution of policing,” said Myron Demkiw, Toronto Police Service Chief, this morning. “These allegations are not representative of the over 8,000 members (of Toronto Police Services). We are a big organization, from the human race, and we have incredible controls, incredible systems, incredible training, and importantly in this case, recognized that when something did go wrong we found it. We were able to tackle it, and we’re able to put people before the courts where they belong.”

TPS Chief Demkiw said it was the most significant internal investigation of police officers in his 35 years on the force. He added he is pushing for suspension without pay, for at least four of the seven officers, “where the law permits me to do that”.

Trust in Policing Shaken

A police source who first heard about the arrests yesterday told Casino.org the arrests are “terrible … does nothing good for the organization’s reputation”.

York Regional Police has been quarterbacking an ongoing illegal gambling and extortion investigation, in partnership with South Simcoe Police Service and Toronto Police Services. We wrote about it in mid-January.

In January, Thomas Phippard commonly known as “Frank the Tank”, was charged with Extortion x3, Utter Threats. John Madeley, a recently retired Toronto cop, was charged with Breach of Trust, Unauthorized Use of Computer x4, Possession of Property Obtained by Crime Under $5000, Possession of Fireman at Unauthorized Place, Possession of Prohibited Device x2.

Extortion Investigation

The police said the two men, working with an organized crime group, would give victims access to gaming websites where players would place bets on credit. The activity occurred between January 2024 and October 2025. Those who lost their bets were required to pay their debts in cash, sometimes in exaggerated amounts. The suspects used intimidation and threats of violence to collect the debts.

Phippard had been charged originally with 11 offences in connection to the ongoing investigation last fall.

The probe which led to today’s charges in part stemmed from the Madeley arrest. Madeley’s son was also allegedly involved. Madeley retired from the police force April 1, 2025, after 28 years of service.

According to the inside police source, Madeley resigned to avoid prosecution and “keep his pension”, and Phippard oversaw the collection of money owed in the illegal gambling operation.


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