The homes of two executives tied to Canadian waste management giant GFL Environmental Inc., including the company’s chief executive officer, were shot at within one hour of each other in Toronto. The shootings, which are being investigated by Toronto Police’s guns and gangs unit, took place late Sunday and early Monday in separate areas of the city, but both locations are among the wealthiest pockets of Toronto. Police believe the incidents are connected and that the houses were targeted.

GFL, which is traded on the Toronto Stock Exchange and the New York Stock Exchange, is a serial acquirer of smaller rivals and has become one of the four largest waste management companies in Canada and the U.S. GFL’s largest shareholders are private equity firm BC Partners and the Ontario Teachers’ Pension Plan, and the company currently has a $20-billion market value.

Recently, GFL has been hampered by the debt accumulated to fund its acquisitions and management has said they were considering auctioning off the company’s environmental services division, which offers liquid waste management and soil remediation services, to raise billions of dollars for debt repayment.

GFL CEO's Home Targeted

The first shooting took place at 11:52 p.m. Sunday in Rosedale at the home of GFL founder and CEO Patrick Dovigi. In an interview, Mr. Dovigi confirmed the shooting, saying someone ran up to the side door of his house and tried to get in but couldn’t because the door is metal. After a security guard approached, the man ran away and fired shots that Mr. Dovigi said mostly went into the ground.

What appeared to be a bullet hole could be seen on the brick exterior of the sprawling property early Tuesday, and a security guard was parked in the driveway outside. Police also said a car was hit in the attack. Mr. Dovigi spends most of his time in New York and Miami and was not home at the time of the shooting.

Second Shooting One Hour Later

A second house was shot at one hour later, at 12:58 a.m. Monday. The home belongs to Ted Manziaris, who is a long-time business partner of Mr. Dovigi’s. Mr. Manziaris is currently a consultant in the GFL family of companies, advising an arm called Green Infrastructure Partners whose services include road paving, demolition, excavation and remediation.

On Tuesday morning, a tradesman was patching up nine bullet holes on the front door of Mr. Manziaris’s home in the York Mills neighbourhood. A woman who answered the door declined to comment.

No injuries were reported in either incident and investigators have canvassed both neighbourhoods, where most of the homes have security systems and surveillance video. A neighbour of Mr. Manziaris’s said security footage showed a black car outside the Manziaris property at the time of the shooting. The Globe and Mail is not identifying him as he was concerned for his family’s safety.

A History of Partnership

Mr. Dovigi and Mr. Manziaris go back more than a decade. Fresh out of university, Mr. Manziaris co-founded a company called Turtle Island Recycling Corp. that focused on non-hazardous solid waste and recycling collection services for commercial and industrial customers in the Greater Toronto Area. Turtle Island was sold to GFL in 2011.

At the time, GFL, which is based in Vaughan, Ont., was starting to build its empire through acquisitions and the company has grown rapidly since. As a serial acquirer, GFL plows its operating cash flows into new corporate buyouts and the company has lost more than $2-billion since the start of 2020.

GFL’s growth has made Mr. Dovigi very wealthy and the CEO recently paid US$59.75-million for an Aspen, Colo., house formerly owned by actor Jack Nicholson.

Green Infrastructure Partners

The company Mr. Manziaris currently consults for, Green Infrastructure Partners, or GIP, was created in 2022 by Mr. Dovigi. The division houses some units that used to operate inside GFL, and GIP also purchased Coco Paving, a family business run by siblings Jenny and Rock-Anthony Coco that predominately operates in Ontario. GIP teamed up with New York-based HPS Investment Partners Inc. to purchase the paving company for an undisclosed sum.

Beyond GFL, Mr. Manziaris has had his hand in a number of other companies, including founding Edgefront REIT, a publicly traded company listed on the TSX Venture Exchange that has since evolved into Nexus Industrial REIT.

His other business ventures include partnering in the Seattle Kraken, an NHL expansion team, and buying GP8 Oxygen Water, a bottled-water company that uses a “revolutionary electrolysis process to increase the solubility of oxygen.”

Mr. Manziaris did not return a request for comment.

A Wave of Crime in Toronto

The shootings come amid a surge in violent crime in Toronto. In recent months, the city has seen a spike in carjackings, robberies, and other violent crimes. This has led to calls for increased police presence and tougher penalties for criminals.

The shootings at the homes of GFL executives have raised concerns about the safety of wealthy residents in Toronto. Some residents have expressed fear that they are becoming targets of criminals.

Police are investigating the shootings and have not yet released any suspects. However, the incidents have highlighted the growing problem of crime in Toronto and the need for effective solutions to address it. The city’s mayor has pledged to address the issue, but it remains to be seen what steps will be taken to ensure the safety of residents.

A City in Crisis

The shootings in Toronto's affluent neighborhoods are a stark reminder of the city's struggles with crime. While the police are investigating these incidents, many residents feel that the city is losing its grip on security. The recent surge in carjackings, robberies, and other violent crimes has made many people nervous about their safety, especially in the affluent neighborhoods where these incidents have taken place. These incidents underscore the need for the city to address the root causes of crime and find effective solutions to ensure the safety of all its residents. The city's leadership must prioritize public safety and work collaboratively with the community to restore order and prevent future incidents.