At 1 a.m. on March 25, a gunman approached the gate surrounding the Woodbridge, Ont., mansion of Paul Borrelli – an executive at Green Infrastructure Partners Inc. (GIP), the sister construction company to Canadian waste giant GFL Environmental Inc. – and sprayed the front of the property with bullets.
A few days earlier, a similar scene played out in midtown Toronto, when around 2 a.m. a gunman opened fire on the home of Mr. Borrelli’s GIP colleague Sean Goldberg, the son of investment banker Barry Goldberg, who helped finance GFL in its early days.
These recent shootings were the second time that executives connected to GFL have had their homes targeted in back-to-back assaults.
Private security guards patrol outside the home of GIP executive Paul Borrelli in Woodbridge, Ont., where a gunman opened fire on March 25.Sammy Kogan/The Globe and Mail
In September, 2024, an armed assailant shot at the residences of GFL chief executive officer Patrick Dovigi and his long-time business associate, Ted Manziaris, who now works with GIP. These were part of at least a dozen attacks on GFL and GIP properties and equipment – shootings, vandalism and suspected arsons – since June, 2024.
Police have arrested a couple of the alleged triggermen, including an 18-year-old who was apprehended shortly after the shooting at Mr. Borrelli’s home. However, police believe these shooters were hired guns, acting on the orders of someone else.
While detectives had revealed almost nothing about their probe, court documents show that hours after the September, 2024, shootings, police began investigating whether the attacks may be linked to an increasingly bitter feud between a handful of GIP executives and the owner of a Toronto excavating and shoring company.
That owner is 42-year-old Ilan Philosophe, the founder of Astro Excavating Inc. and its offshoot company, Astro Shoring Inc.
Ilan Philosophe, owner of Astro Excavating and Astro Shoring.
In April, 2025, Toronto police laid a criminal harassment charge against Mr. Philosophe over a series of taunting and often vulgar text messages that he had been sending to GIP officials. At that time, Mr. Philosophe spoke to The Globe and Mail. It was the first of what would become several interviews over the past year. In those conversations, he categorically denied being involved in any of the violence.
“I have absolutely nothing to do with any of this, attacks or anything, on GFL. That’s 100 per cent,” Mr. Philosophe said in one interview. (Mr. Philosophe refers to GFL and GIP interchangeably.) It’s a denial he resolutely maintains today.
However, on Thursday – following a year-and-a-half-long investigation – Toronto’s guns and gangs unit charged Mr. Philosophe in connection to the attacks on Mr. Dovigi’s and Mr. Manziaris’s homes. Mr. Philosophe was charged with two counts of discharging a firearm in a place that is reckless to others, and two counts of conspiracy to commit an indictable offence. He has not been arrested in connection to any of the other attacks on GFL or GIP.
A GIP project site in Toronto in August, 2025. GIP, the sister construction company to Canadian waste giant GFL Environmental Inc., handles everything from demolition to road paving to condominium builds.Sammy Kogan/The Globe and Mail
In a statement from his lawyer Friday afternoon, Margaret Bojanowska, Mr. Philosophe maintained his innocence.
“At this time the defence has very little information and we look forward to receiving the disclosure so that we can mount a challenge to the information in Court,” she said in an e-mail to The Globe.
The assaults on one of Canada’s most dominant industrial companies have made headlines across the country and forced Mr. Dovigi to address the violence with investors.
GFL services hundreds of municipalities in Canada and the United States and has a market value around $22-billion on the Toronto Stock Exchange. GIP, which was spun out of GFL as a stand-alone company in 2022, has become a major infrastructure player. (GFL remains one of GIP’s major shareholders.) GIP handles everything from road paving to excavation and demolition.
That charges have been laid against a GIP competitor is another twist in a saga that has roiled some of Toronto’s most affluent neighbourhoods, rattled the publicly traded company and shaken its top executives.
A private security vehicle guards the midtown Toronto home of GIP executive Sean Goldberg, after it too was the site of a targeted shooting in March.Sammy Kogan/The Globe and Mail
For months, the violence has been the talk of construction sites and Bay Street alike, bringing the stuff of underworld television dramas, chillingly, to real life. In the end, court records suggest that the case is born of business, bad blood and competition for contracts in the fiercely competitive world of waste and construction.
Launched in 2014, Mr. Philosophe’s company, Astro, has become a staple in the Greater Toronto market, particularly in high-rise residential and commercial development, occasionally playing in the same space as GIP. The two companies once had a good working relationship and, in fact, Astro has used GFL facilities to dispose of contaminated soil.
But in interviews with The Globe, Mr. Philosophe says things took a turn more than two years ago, after he alleges GIP tried – but failed – to steal one of Astro’s contracts. (GFL denies this happened.) Mr. Philosophe says GFL then made an offer to buy his company, which he refused. (GFL is adamant that this didn’t happen.)
In Mr. Philosophe’s telling, after he declined the offer, GIP and GFL executives began spreading rumours about him and Astro to current and potential clients, criticizing his character and his company’s professional capabilities, among other things. These are more accusations that GFL denies.
There have also been other disputes between the two companies that created tension. In late 2023, Mr. Philosophe terminated the man he hired to run Astro Shoring, and shortly afterward, that man took a senior position with GIP.
A truck from Turtle Island Recycling Corp., which was co-founded by Mr. Manziaris, arrives at the transfer station in Windsor, Ont., in 2010. The company was bought by GFL in 2011, one of more than 270 acquisitions that GFL has made since its founding in 2007.GEOFF ROBINS/The Globe and Mail
Mr. Philosophe says he grew tired of feeling bullied by an industry Goliath that has a history of scooping up smaller players. Since its founding in 2007, GFL has acquired more than 270 companies. Frustrated, he began sending increasingly volatile text messages to a handful of GIP officials about two years ago, including to Mr. Borrelli and Mr. Goldberg, whose homes were sprayed with gunfire two weeks ago.
“I’m gonna tell you something right now. I have, I have pain inside of me, so I can be rude sometimes,” he said last April. “I can get a little bit emotional. I get burned. Send messages that are rude.”
In another interview, he said: “I regret sending them very much. It was a very poor decision. It’s unprofessional. It’s humiliating. And I’ve done a lot of hard work since then to handle my emotions in a healthier way. I’ve done a lot of personal work to grow from this.”
Mr. Philosophe says that, as a young guy, he was never part of the “cool club” but he stood up to bullies, “and GFL are the biggest bullies you’ll ever meet. If they can’t stop you, buy you, control you, they’ll just do everything to ruin you.”
Astro’s founder shared with The Globe many of the inflammatory texts that he sent to GIP executives. The messages mock GFL for using debt to finance its rise and suggest GFL executives are jealous of Mr. Philosophe for building his business by simply working hard: “you will never keep up, I have the energy to go 24/7.”
A screenshot of text messages allegedly sent by Ilan Philosophe. This image was part of a warrant application prepared by the Toronto Police Service and submitted in April of 2025. Redactions by The Globe and Mail.Toronto Police Service/Supplied
But Mr. Philosophe can also be menacing, and at one point he joked about the shootings: “Oh ya, I own 100% of my company too … who shot ya??” (In an interview, Mr. Philosophe says this was a reference to a song title by the hip-hop artist The Notorious B.I.G.)
The messages also often use crude language and homophobic slurs. “No financial engineering here ... just straight up gangster business, zero debt and life like a real fucking boss.”
GFL and GIP officials tell a different version of events.
According to police documents, these executives said that they became wary of Mr. Philosophe because of his text messages and other behaviours.
Early last year, GIP took the text messages to police and alleged harassment. In April, 2025, the Toronto police guns and gangs unit raided Mr. Philosophe’s penthouse suite near Upper Canada College as well his two cars, seizing multiple cellphones and computers.
Afterward, police laid the criminal harassment charge relating to the text messages. He was not arrested at the time for the attacks on GFL or GIP. However, a search warrant application filed by police ahead of the April, 2025, raid indicates he was being considered as a potential suspect in connection to the shootings. (The allegations contained in the warrant application have not been tested in court.)
That 37-page document, which was obtained by The Globe, provides a window into the GFL attack investigation and the parallel fight that has played out between Astro and GIP.
Mr. Philosophe has always maintained that the text messages were his only response to what he believes were GFL’s attempts to tarnish his company’s reputation.
That makes them the real villains. “They’re out to try to get Astro’s name completely destroyed,” he said.
There are three pieces of art in Mr. Philosophe’s living room. One is a large, black and white photograph of an Astro heavy excavator working on a dig site. Another is a stylized pop art collage, featuring a portrait of him, images of machinery, Astro’s logo in gold and the phrase “From Nothing to Something.” Tucked beside the fireplace is an oversized life-like model of another excavator. He lives and breathes his work.
Mr. Philosophe’s suite is also Astro’s head office, where he takes meetings and handles the company’s accounting, invoices and payroll.
“I want to be an open book,” Mr. Philosophe said, sitting at his kitchen table the afternoon after the raid and his criminal harassment charge.
Mr. Philosophe grew up with a front-row seat to wealth and business – although it was not his own.
His uncle, Isidore Philosophe, co-founded Cinram International, once a prominent manufacturer of CDs and DVDs listed on the Toronto Stock Exchange.
Mr. Philosophe’s uncle Isidore Philosophe, co-founder of once-prominent CD and DVD manufacturer Cinram International, was an early backer of Astro Excavating, giving his nephew a $50,000 loan in 2014.DEBORAH BAIC/The Globe and Mail
As for his own home, Mr. Philosophe says he grew up in Thornhill, Ont., in a household that was at times tumultuous. He moved out at age 17 and got a job at a recruitment firm, where he met executives in the construction and high-rise industry. An entrepreneur at heart, he opened his own shop, ISP Direct Staffing, in 2010 and it was through that business that he was introduced to the excavation world, where he spotted an even bigger opportunity.
“He’s extremely bright and he’s a real entrepreneur,” his now-retired uncle Isidore said in an interview conducted before the latest charges.
With a $50,000 loan from his uncle – which Isidore says his nephew quickly repaid – Mr. Philosophe launched Astro Excavating in 2014. (He started the company with a partner, who also put in $50,000. Records show Mr. Philosophe bought out this individual about two years later.)
“The first three years, I used to have panic attacks every time I would take a hot shower. Because every dollar was do or die,” Mr. Philosophe said. The goal was to have Astro operate lean, and he was obsessive about streamlining production to keep costs as low as possible.
With each successful job, Astro began making its mark in the industry, winning bigger and more prestigious contracts. A few years ago, it landed a job with its first top-tier developer – Menkes Developments Ltd. – for a downtown Toronto high-rise condo building. And in 2021, with more than 100 excavations under his belt, Astro Excavating expanded into the shoring world as well, launching Astro Shoring. (Excavation is digging a hole. Shoring is securing the walls around the hole.)
It’s at this moment, with Astro on the map, Mr. Philosophe said, that he started to attract the attention of competitors such as GFL, a behemoth in the industry.
But Mr. Philosophe has always felt that the way GFL has grown is distasteful.
GFL CEO Patrick Dovigi founded his company in 2007, and through the years, GFL expanded into lines of business that overlap with Mr. Philosophe’s companies.Sammy Kogan/The Canadian Press
Founded in 2007 by Mr. Dovigi, a charismatic and ambitious young hockey player from Sault Ste. Marie, Ont., GFL started out as a small Toronto waste management company that seized on an opportunity to execute a classic roll-up strategy. This meant adding scale by snapping up everything it could. The more of the waste supply chain that GFL controlled, Mr. Dovigi figured, the more profitable the company would be.
One of his first major buys, in 2011, was Turtle Island Recycling Corp., which was co-founded by Mr. Manziaris. Backed by private equity money, he kept expanding rapidly across Canada and the U.S., and GFL blossomed into North America’s fourth-largest waste management company. In 2020, GFL went public on the TSX. The following year, Mr. Dovigi sensed an opportunity to expand more into infrastructure and construction, so GFL purchased Coco Paving Inc., one of Canada’s biggest road-building companies, for an undisclosed sum.
Investors loved the never-ending growth, but there was a catch. The aggressive acquisition strategy was fuelled by debt, and interest payments on what grew to be a $9.6-billion debt load sapped GFL’s cash flow – something the company’s investors often tolerated, but which rubbed Mr. Philosophe the wrong way.
Through the years, GFL expanded into lines of business that overlap with Mr. Philosophe’s companies, and in his telling, the first major conflict between the two came in late 2023.
Astro had been contracted to do a job for Marlin Spring Developments, but things stalled over concerns about the ground conditions. According to two people with knowledge of events, Marlin Spring came to have doubts about whether Astro was capable of handling the complicated work. Marlin Spring reached out to GIP to quote the job.
When Mr. Philosophe learned about this, he was furious. To his mind, Astro was more than capable of managing the difficult work. In the end, he came to blame Astro Shoring CEO Graeme Smart and GIP. Mr. Philosophe believed the company – specifically, an executive named Toben Jerry, with whom he had previously had a friendly relationship – had gone behind Astro’s back to sow doubt and steal the contract. (Mr. Jerry says this absolutely didn’t happen.)
In a statement to The Globe, GFL said that Marlin Springs had been a customer of theirs since 2000: “It is ultimately the customer that issues tenders and is responsible for selecting a vendor of their choice, based on price and qualifications.”
Astro ended up keeping the job. But in October, 2023, Mr. Philosophe fired Mr. Smart. Within a few months, Mr. Smart was working as a vice-president at GIP.
It was at that time, that Mr. Philosophe began sending the text messages, especially to Mr. Jerry.
Around the same time, Mr. Philosophe alleges that GFL – through Mr. Goldberg – floated the idea of an acquisition. In early 2024, Mr. Philosophe says a verbal nine-figure offer was made, but he tried to brush it off.
“I basically said, look, I’m not interested in selling my company. I’m not for sale. It doesn’t even matter if it’s a billion,“ he said. ”I love what I do.”
Mr. Philosophe alleges GFL, which denies any offer was made, did not like being rejected and began to retaliate against him. The perceived slights – and Mr. Philosophe’s text messages – worsened after this.
Mr. Philosophe alleges that after the September, 2024, shootings, GFL executives began telling people in the industry that he was behind the attacks. He says he lost business because of it.
Despite the whispers, he said, he heard nothing from police until they knocked on his door in April, 2025, with the search warrant.
Mr. Philosophe was charged at that time with criminal harassment, and barred from communicating with a number of GFL and GIP officials: Mr. Dovigi, Mr. Manziaris, Mr. Smart, Mr. Jerry, Mr. Goldberg and Mr. Borrelli.
His next appearance on the criminal harassment offence is Sept. 10.
In late October, 2024, employees arrived to work at a GFL office building in north Toronto to find the glass front entrance shattered, with bullet holes in the front door’s metal frame and the front wall.Robyn Doolittle/The Globe and Mail
Before conducting a raid on someone’s home and seizing their property in a criminal investigation, police must outline their case to a judge in order to obtain a warrant.
With the GFL investigation, the warrant application provides new details and allegations about some of the incidents. None of the evidence contained in the document has been tested at a trial, and because warrants are obtained without the knowledge of the person being searched, Mr. Philosophe has never had an opportunity to push back against its conclusions.
Early on in the document, the police include a section that outlines the background of their investigation. This part begins with a detailed description of the attack on Mr. Dovigi’s home on Sept. 29, 2024.
The document explains that, on the night in question, a security guard was parked in front of Mr. Dovigi’s Rosedale home. Around 11:45 p.m., the guard watched a dark-coloured sedan do a U-turn on the street before parking in front of the mansion.
Surveillance footage from the scene showed a male in a hooded black sweater with three white stripes and black face mask walking toward the front of the house holding a handgun and a cellphone. He fired a volley of shots at the property and at least one toward the security vehicle, the application alleges.
About an hour later, just after midnight on Sept. 30, surveillance video captured images of a man with the same description – black hooded sweater with three white stripes and a black face mask, carrying a handgun and a cellphone – firing nine shots at Mr. Manziaris’s front door. The assailant “appears to be filming the shooting,” the warrant application says.
The police document also reveals that Mr. Manziaris’s home had been targeted a week earlier as well, on Sept. 21. In that case, an unknown male wearing a black balaclava smashed the Ring doorbell camera and two front windows. The case had initially been investigated as a possible break-and-enter attempt.
On Sept. 30, 2024, nine bullets were fired through the front door of the home of Ted Manziaris, an executive at GIP.Robyn Doolittle/The Globe and Mail
But it wasn’t until the shootings that GIP officials raised concerns about Mr. Philosophe. The warrant shows that on Sept. 30, someone from GIP told police that “the company has been having ongoing difficulties with the owner of Astro Excavating Inc. named Ilan Philosophe.”
In addition to mentioning the text messages, the official mentioned that Mr. Philosophe had recently been removed from a Toronto job site by police.
The warrant application says the incident occurred in Toronto on Sept. 6, 2024, and alleges that Mr. Philosophe had been hired to do foundation work on a new building. There was a dispute between the developer and Mr. Philosophe, which resulted in Astro’s contract being terminated and police being called.
The warrant application provides few details, however, Astro filed a breach-of-contract lawsuit against the developer, CB Wilkinson. Court records filed as part of this continuing litigation – none of which have been tested in court – indicate that Astro had raised concerns about the ground conditions and drilling strategy. Mr. Philosophe accused the developer and its consultants of ignoring Astro’s concerns.
The developers’ statement of defence alleges that on the morning of Sept. 6, 2024, Mr. Philosophe showed up and began causing a disturbance.
Mr. Philosophe ”became outraged and began to yell and swear ... and proceeded to move about erratically using loud and abusive language,” the document alleges.
Speaking to The Globe, Mr. Philosophe denied that he lost his temper: “I was not in the least bit erratic. It was the opposite. The owner was being erratic and having a tantrum ... I was never removed from the site by police.”
Mr. Philosophe said the fact that GIP raised this incident in an interview with police is an example of how the company spreads rumours about him, since GIP wasn’t involved.
However, once Astro was removed, the developer hired GIP to take over the job. In a statement, a GFL spokesperson said that CB Wilkinson has been another long-time customer of GIP. “We responded to a tender and were awarded the contract.”
This Sept. 6 incident was noteworthy to the GFL police investigation, because Mr. Philosophe provided officers with a cellphone number at the time – a 416 area code number – that became part of the GFL probe. A second number connected to Mr. Philosophe – this one area code 437 – was also highlighted in the warrant application.
Both numbers were run through police databases and additional warrants were used to collect call records for both. The warrant application alleges that the 437 number received suspicious messages from another cellphone on Sept. 21, 2024, and Sept. 29, 2024, around the time of the attacks.
However, there is no indication in the warrant application that detectives had been able to definitively link the 437 number to Mr. Philosophe. And there’s no proof that the sender of those messages was involved in the shootings.
The next major event in the investigation, the application shows, seems to have occurred on March 17, 2025, when another GIP executive spoke to police about “disturbing texts” that Mr. Philosophe had been sending to some GFL executives for more than a year. Some of these texts referenced the shooting.
According to the officer’s notes, which are included in the application, Mr. Philosophe messaged a group chat with GIP officials in mid-March. In one expletive-laden text, Mr. Philosophe sent a video of Mr. Dovigi doing a media interview about the shootings.
“You guys are soft. ... Your bosses are scared of me and I look forward to playing with you,” Mr. Philosophe is alleged to have written. “Welcome to real life, real animals who built their empire without debt.”
Toronto Police Service’s 32 Division in North York, where Mr. Philosophe was taken on Thursday when its guns and gangs unit charged him in connection to the attacks on Mr. Dovigi’s and Mr. Manziaris’ homes.Sammy Kogan/The Globe and Mail
A few weeks later, police filed their warrant application, eventually laying the criminal harassment charge.
In an interview after his last court appearance on the criminal harassment charge – but before his latest arrest – Mr. Philosophe said all he’s done is send text messages, which he regrets.
“It’s not only that I categorically deny being behind these attacks, but I feel like they are looking for a scapegoat to deal with media and shareholder pressure,” Mr. Philosophe said.
On Friday afternoon, Mr. Philosophe made a brief appearance in bail court by video.
Assistant Crown attorney Byron Alvares requested that the case be adjourned until Monday: “There’s pending search warrants and further investigations, potential witnesses as it pertains to the conspiracy allegations and the Crown’s waiting to see if more charges might be laid before we embark on considering any releases.”
He is due back in bail court on Monday at 9:30 a.m.
With research from Stephanie Chambers