The trouble with Harry

Canadian businessman Harold Peerenboom is no stranger to feuds, but his latest clash is straight out of a comic book

Harold Peerenboom is rich and resourceful — and has a peculiar way of settling scores.

The 70-year-old Toronto millionaire, who founded one of the top executive search firms in Canada, has never shied away from a scrap. While he has undoubtedly made enemies, even those who have locked horns with him grudgingly admit that he fights with flair and imagination.

There was the time he shone a blinding light into the bedroom of one of his neighbours over a backyard dispute. Or the time he allegedly threatened to build a pig farm next door to a ski club that wouldn't accept his family as members.

Peerenboom's feuds have ranged from the petty to the political, but the one he's waging at his posh condominium complex in Palm Beach, Fla., is a new level of bizarre. The case has stretched on for years and involves an eclectic cast of characters, including the CEO of Marvel Entertainment, high-profile lawyers tied to U.S. President Donald Trump, the Department of Homeland Security, the U.S. Postal Service, Palm Beach detectives and Toronto police.

Both sides have enlisted high-profile lawyers and public relations firms. Peerenboom, for example, has hired PR guru Sallie Hofmeister, who is also representing disgraced Hollywood producer Harvey Weinstein over multiple sexual harassment and assault allegations.

The details are outlandish and hinge on a campaign of vicious allegations about Peerenboom contained in letters sent to fellow residents of the condo complex as well as to Peerenboom's friends, family members and work colleagues in Toronto.

"Once he has decided he's going to pursue a certain path, there's no stopping him."

If you believe Peerenboom, the hate mail campaign stems from a disagreement over a tennis court and can be traced back to fellow condo residents Isaac "Ike" Perlmutter and his wife, Laura, both of whom he has named in a lawsuit.

For all his past bravado, it's possible that this time, Peerenboom has met his match. Ike Perlmutter, 74, is a formidable foe — the reclusive U.S. billionaire is the CEO of Marvel Entertainment and a personal friend of Donald Trump. The powerful Perlmutters not only deny the accusations but have launched a countersuit accusing Peerenboom of stealing their DNA, of all things.

That Peerenboom might go to such extreme lengths to defend his principles is unsurprising to those who have tussled with him before.

"With Harold, in my experience, anything is possible," said John Adams, a former Toronto city councillor who inadvertently became Peerenboom's target when he tried to arbitrate a dispute between him and his neighbour.

Adams's brush with the millionaire taught him that Peerenboom can be "very creative" and "would leave no stone unturned in advancing his side of the case."

Which is why Peerenboom has shown no signs of relenting in his six-year fight with Perlmutter.

Peerenboom turned down requests for an interview with CBC News. When this reporter knocked on the door of his mansion in north Toronto, Peerenboom would only respond through his intercom system: "I don't speak with the press, but I appreciate you dropping by."

Those who know Peerenboom say that like many of his skirmishes, the Palm Beach dispute is really about his sense of justice and need to right a perceived wrong.

"Once he has decided he's going to pursue a certain path, there's no stopping him," said former Conservative cabinet minister Lisa Raitt, who has known Peerenboom for years. "Time does not stop him. Distance does not stop him. Space does not stop him. He will continue on the path that he chooses until he gets a result."


"I'm going to be a very rich man one day." Those were Peerenboom's words back in 1975, when he was one of a number of Toronto business professionals profiled in a Toronto Star series called "The young achievers."

He was 27 at the time and in the span of five years had built up an executive search firm to the point where, according to one person cited in the profile, he was on "first-name terms" with most of Canada's top executives.

Back then, Peerenboom was a flashy figure, riding around Toronto in his yellow 1974 Rolls Royce — part of an image, he would later say, meant to show people he didn't need their money.

Born in Port Arthur, Ont., and raised in Fort William (both of which were eventually absorbed into Thunder Bay), he didn't come from money and arrived in Toronto with none. Peerenboom, who is of Dutch descent, shortened his last name to Perry to make it easier for others to remember. He worked as a district circulation manager for the Toronto Star and later learned the business of headhunting when he joined a Toronto-based U.S. recruiting firm.

In 1970, he decided to strike out on his own, creating Mandrake, which grew to be one of Canada's largest headhunting firms, placing executives in some of the top companies throughout the country. (Peerenboom told the National Post in 1999 that as a headhunter, he collected $1.3 million annually in fees.)

Peerenboom's fighting spirit also drew him into the political arena. In 1969, he ran for alderman, losing to Art Eggleton, who would go on to be mayor and a federal Liberal cabinet minister. Peerenboom himself was a capital "L" liberal and a financial backer of the federal party, which would later help him realize his political ambitions. In 1995, Transportation Minister David Collenette, a friend, appointed him to the Toronto Harbour Commission. Peerenboom became chair three years later, foregoing the annual salary and accepting $1 a year for the job.

At the time, Peerenboom was nicknamed "the Commodore," and some said he looked like a riverboat gambler, with his three-piece suit and pocket watch. Peerenboom established himself as a colourful, smart and slightly eccentric character. He was brash and didn't mince words, which made him a favourite source among journalists.

"He had a hell of a swagger," said John Barber, a city hall columnist for the Globe and Mail at the time. In print, Barber described him as "one of the most outrageous figures in Toronto politics" and coined another nickname for him: "Scary Harry Perry."

Peerenboom's time as commission chair was short-lived and marked by controversy. He was criticized for spending thousands of dollars on travel expenses and foreign junkets. The public also got a glimpse of his dogged — and at times impulsive — pursuit of pet causes. Believing some city councillors were on the take from land developers, he hired a private investigator to dig up some dirt. The investigation turned up nothing, and Peerenboom was criticized for wasting $100,000 of taxpayer money on the foolish pursuit.

Peerenboom admitted to the National Post that it was a "debacle."

"That was supposed to be a righteous crusade, but I thought it was a vendetta," said Barber. "You didn't want to get on the wrong side of the guy, because he was just vindictive, and he'd pursue his enemies to the end."

When the commission morphed into the Toronto Port Authority in 1999, the Commodore was unceremoniously dumped by his old friend Collenette, who brought in his own candidates. Peerenboom didn't walk away quietly, suing Collenette and accusing him of sidestepping the proper nomination process.

"Any time I've known Harold to be in a dispute, once I've learned the details, I thought, most people will walk away and say, 'F--- it, I don't care,'" said a former Mandrake employee who did not want to be named publicly. "But he would say, 'No, now it's the principle of it.'"


Peerenboom's feuds are the stuff of legend, according to Judi McLeod, publisher of the conservative Canada Free Press website. She first met him in 1995, when she ran a small conservative paper in Toronto. Peerenboom was one of the few Liberal Party members who would always be willing to chat and give her the straight goods.

In 1999, McLeod published a piece entitled, "The waterfront's colourful commodore," in which she recounted a tale of Peerenboom attempting to get his kids into a ski club near his family's winter cottage, only to be told there was no room left. Peerenboom apparently responded by telling the club he had purchased the adjacent lot with the intention of starting a pig farm. (Guess who quickly became new members of the ski club.)

"He's got that kind of personality, that he stands his ground on things more than the average person," McLeod said in an interview with CBC News. "Of course, he's a character to boot."

His forceful personality has led Peerenboom into other strange tangles, including a dispute with his neighbours in the tony Toronto area of Forest Hill. In 1997, Peerenboom wanted to build a new gymnasium and indoor pool in his backyard. His neighbour opposed the expansion, concerned that the pool house could be a magnet for prowlers.

Peerenboom decided he would fix that. If his neighbour was so worried about strangers lurking in the shadows, he would just add some lights — ridiculously bright ones. According to John Adams, city councillor for the ward at the time, Peerenboom installed "the equivalent of Pearson Airport landing lights beaming from his property directly into his neighbour's property and windows."

Peerenboom then turned his attention to Adams, who, in his mind, had taken the wrong side when trying to resolve the dispute.

"Harold took umbrage with what I was trying to do," Adams said. Peerenboom publicly announced that he was recruiting other people with the name John Adams to run in the upcoming municipal election — all in an effort to confuse voters and ensure Adams would lose.

Peerenboom never made good on his threat, the lights went away, the dispute was resolved and Adams won his seat.

He may have aggravated one Toronto councillor, but Peerenboom was on good terms with others, including Norm Kelly, who worked with Peerenboom when he was with the Harbour Commission. Kelly called him "very charming, very personable." He considers Peerenboom a city builder and said he was instrumental in the construction of Toronto's island airport.

"He takes on fights I can't imagine even getting involved in."

Friends of Peerenboom contacted by CBC News described him similarly: as an intelligent, philanthropic family man and a loyal friend and colleague.

"He's a good guy. He's a good neighbour," said mutual fund executive Joe Canavan, who has a cottage right beside Peerenboom's on Lake Simcoe, north of Toronto. "Everything I know about Harold is that he's a solid guy, and I suspect if he feels wronged, he's defending his honour."

Indeed, if you're a friend of Peerenboom's, "there's not a thing he won't do for you," said his former employee.

One person who counts himself a friend is Conrad Black. When the former media baron faced tax liens on his home in Toronto's ritzy Bridle Path neighbourhood in 2016, it was Peerenboom who swooped in to purchase the house for $14 million and agreed to lease it back to Black, enabling him and his wife to remain in the mansion that had been in Black’s family for more than 60 years.

"I was trying to assist Conrad out of a difficult situation where if I had not bought the property, he would not be able to live in the house he was raised in," Peerenboom told the Globe and Mail. (Black declined to speak to CBC.)

His generosity extends beyond friendship, Peerenboom's former employee said, pointing out that he has waived tuition for students at the two Toronto private schools he co-founded when families have found themselves in financial straits.

Lisa Raitt was hired by Peerenboom as his executive assistant when he was working for the Harbour Commission and eventually went on to be CEO and president of the Toronto Port Authority. She said she's grateful for the start he gave her, and described him as fearless.

"He takes on fights I can't imagine even getting involved in," she said. "It takes a lot of guts to do it — and he definitely has a lot of guts."

(Philip Street/CBC)

(Philip Street/CBC)

(Philip Street/CBC)


As Peerenboom said back in 1975, he always wanted to be very rich. And having attained that goal, he was able in 2010 to purchase a two-storey, 5,600-square-foot townhome in Palm Beach, Fla., complete with ocean frontage, a saltwater pool and a mantle gilded with 24-carat gold paint. Price: $3.5 million US.

The home is part of a luxury gated community known as Sloan's Curve on a slim strip bordered by Lake Worth Lagoon on the west and the Atlantic Ocean on the east. Peerenboom moved in soon after he bought it, but kept his Forest Hill home in Toronto.

The Sloan's Curve complex has two oceanfront buildings with shared amenities, including a pool, exercise facilities, private beach access and six clay tennis courts. Despite these comforts, less than a year after he moved in, Peerenboom started getting irritated with how certain parts of the complex were run.

Specifically, he didn't like how the tennis courts were being managed.

A woman named Karen Donnelly had been doing the job for more than 25 years, but she had been doing it without an approved contract. Peerenboom argued that under Florida law, the contract for management of the tennis facility must be submitted to a competitive bidding process.

And Peerenboom made a stink about it.

He confronted the Sloan's Curve Homeowners Association, but a number of longtime residents opposed the changes he was asking for.

"He's just a braggart, a blowhard. He sues everybody he gets a chance to sue."

"Look at it this way," said resident Stephen Raphael. "You live in a community, and you're a tennis player, and you've been friendly with this woman, very nice lady, who's been doing it for 25 years.

"Everything is smooth, everybody likes her, nobody says a bad thing about her. All of a sudden, Harold Peerenboom decides her contract should be put out for the bid. So, most people — everybody I know — thought that was ridiculous."

In raising the issue, Peerenboom set himself on a collision course with Isaac Perlmutter.

Perlmutter and his wife, Laura, had moved to the area in 1991 — their condo is in one of the oceanfront buildings down the street from Peerenboom's. Forbes magazine has listed Perlmutter's wealth as $4 billion US — not bad for a former Israeli soldier, veteran of the Six Day War, who, according to business folklore, landed in the U.S. with only $250 to his name.

Perlmutter began by selling toys on the streets of Brooklyn, a venture he later turned into a successful company called Toy Biz. By most accounts, Perlmutter isn't much of a comics nerd, but he knows what sells, which led him to Marvel in 1998. When the comic book publisher found itself on the brink of bankruptcy, Perlmutter swooped in to take control.

He reversed the fortunes of the company and later sold a majority stake to Disney for $4 billion, becoming one of the largest Disney shareholders in the process.

Perlmutter has been labelled eccentric and authoritarian, and his reputation for frugality is legendary. According to a profile in The Daily Beast, he wanted to serve only potato chips at the 2008 premiere of Iron Man and has been known to salvage "perfectly good" paper clips from the garbage can. He guards his privacy as tightly as Spider-Man protects his identity — so much so that he reportedly came to the Iron Man premiere disguised in glasses and a moustache. Perlmutter doesn't give interviews — and would not speak to CBC — and is rarely photographed in the press.

At Sloan's Curve, Perlmutter found a friend in Karen Donnelly. He liked that she was usually available when he needed a tennis partner.

But around the time that Peerenboom started making noise about the tennis courts, Donnelly became the target of an anonymous memo circulated among residents of Sloan's Curve that accused her of bid-rigging, conducting her real estate business from the property and violating tax and licensing regulations. In April 2011, Donnelly sued two residents of the complex, accusing them of slander and later adding Peerenboom as a defendant.

Donnelly eventually dropped her suit, but Peerenboom felt he had been wrongfully accused and sued her for malicious prosecution.

"He's just a braggart, a blowhard. He sues everybody he gets a chance to sue," said Raphael, who himself is suing and being sued by Peerenboom for malicious prosecution.

Another Sloan's Curve resident, Maurice Herman, said he believed Peerenboom had a valid point about the contracting process.

"Somebody stuck their finger in his eye, and he struck back," said Herman, who said he never uses the tennis court. "And I say, good for him."





In 2011, the Sloan's Curve saga took a mysterious turn. Envelopes were sent to members of the High Ridge Country Club, many of whom were also residents of Sloan's Curve.

Unsigned and with the club as the return address, they contained 12 pages of online news articles from Toronto media outlets that were critical of Peerenboom, focusing on his political controversies and his role as chair of the Toronto Harbour Commission.

Peerenboom had clearly annoyed someone, but these letters were tame compared to what was to follow.

A year later, more letters went out. These were postmarked with a West Palm Beach zip code and sent to Peerenboom's family, friends, neighbours and Mandrake colleagues. The letters contained warnings to the recipients to protect themselves from Peerenboom. Most troubling was the false allegation that Peerenboom had been involved in the sexual assault of a boy and that he had bribed the child's mother to keep quiet.

Peerenboom notified the U.S. Postal Inspection Service and the West Palm Beach Police Department, who opened an investigation.

Over the next couple of years, more anonymous letters showed up around Sloan's Curve. In one, Peerenboom was accused of being involved in a double homicide in Hallandale Beach, Fla., in January 2013. The accusation hit close to home — one of the victims, Rochelle Wise, had been a director of Crestwood School, one of several Toronto private schools Peerenboom co-founded. Hallandale detectives ended up interviewing Peerenboom about the murders but quickly concluded he had nothing to do with them.

Another bizarre letter, this one meant to look like Peerenboom himself had written it, was filled with anti-Semitic invective and endorsed Hitler's final solution.

In March 2014, Peerenboom received a letter at his condo expressing regret that the Toronto businessman had "cheated death" in a recent car accident. (Peerenboom was seriously injured in the crash.) Inside the envelope, the sender had included other letters meant to look like Peerenboom had written them. The anonymous author suggested these letters had been sent to prisoners across the U.S. and Canada and included insults and racial epithets against the inmates — all part of a plan, the letter writer said, to incite "these bad men" to pursue Peerenboom.

Then came a demand: "No one will be happy until you leave our neighbourhood — until you leave Sloan's Curve — get out now."

In Peerenboom's mind, it was clear who was behind this campaign: Perlmutter.

He had a close relationship with Donnelly and had privileged access to the tennis facilities under her management, so to Peerenboom, it made sense that he would oppose any moves to oust her.

Peerenboom hatched a plan.

In February 2013, Perlmutter and his wife were asked to testify in the slander dispute between Donnelly and Peerenboom. They went to a deposition hearing at a West Palm Beach law office, where they ended up looking over a number of documents and answering questions.

It's unclear whether or not the deposition was legitimate, but according to a later statement by the Perlmutters in court, the documents they handled had been specially treated to pick up DNA from their fingertips. Plastic water bottles and a bottle cap the couple had used were also collected in hopes of obtaining a DNA sample. The purpose was to see if the DNA of either Perlmutter would match DNA found on the hate mail.

"I read that and said, 'Oh God, that's so Harold,'" said Peerenboom's former employee.

Philip Street/CBC

(Philip Street/CBC)

(Philip Street/CBC)

Was a match found? Well, it depends on whom you ask. Peerenboom's legal team insists that a DNA laboratory concluded that Laura Perlmutter's DNA, collected from her plastic water bottle, was a match with DNA retrieved from one of the letters.

The Perlmutters dismiss the claim. They say the so-called match was made by a lab that "lacks any of the equipment, accreditation or expertise" needed to make such a determination. Indeed, the Perlmutters claim the lab shipped the DNA samples to another lab in Nevada, which excluded the Perlmutters' DNA.

Either way, the Perlmutters were furious.

Undaunted, Peerenboom launched a lawsuit a few months later against the Perlmutters and ten other people, most of them residents of Sloan's Curve, accusing them all of slander, emotional distress and civil conspiracy. The letter-writing campaign, Peerenboom claimed, constituted "a pattern and course of conduct that is extreme, outrageous, malicious and shocks the conscience in that it lies far beyond the bounds of common decency and basic respect required by civilized society."

Peerenboom attempted to get telephone records, emails, letters and DNA samples from those named in the lawsuit. But in 2014, he amended the suit and dropped everyone but the Perlmutters as defendants.

The next year, the Perlmutters launched their own lawsuit against Peerenboom, claiming he had stolen their DNA. They cited a Florida statute they say prohibits the collection of DNA without prior permission. Peerenboom's legal team has countered that the Perlmutters' interpretation of the law is too broad and that the police were aware of what Peerenboom planned to do and expressed no misgivings.

Regardless, obtaining the Perlmutters' DNA has put Peerenboom on the defensive. A Florida state judge ruled last January that the Perlmutters' case could go forward. The question of what rights one has to one's own DNA is a legal grey area, meaning a judgment in the suit could have broader ramifications.

The case has since turned into an epic battle between two legal titans: Marc Kasowitz, one of Trump's lawyers, who is representing Peerenboom; and Roy Black, a famed Florida-based defence attorney whose clients have included Justin Bieber, William Kennedy Smith and the creator of the video series Girls Gone Wild.

In an interview with CBC News, Black acknowledged the scale of this legal scrap is out of proportion with the original dispute, which was ostensibly over a tennis court.

"With the expenses of these lawsuits, they could have recreated the U.S. Open tennis facilities there," Black said.


In November 2015, Peerenboom came upon what he believed was the smoking gun that would allow him to finally implicate Perlmutter in the hate mail campaign. After forcing Marvel to produce emails related to the case, Peerenboom's legal team discovered that it had been Isaac and Laura Perlmutter who had sent the negative press clippings about Peerenboom in 2011. To Peerenboom, this was a sure sign that they had also sent the more vitriolic letters that came later.

The Perlmutters and their lawyer, however, dismissed the significance of this apparent bombshell. Peerenboom had stirred up trouble over the tennis courts, and Perlmutter had just been letting Sloan's Curve residents know whom they were dealing with, they said. The articles were all available online, and none of them would be considered hate mail, Black argued.

A couple of months later, the case took another weird turn.

In January 2016, customs agents in Detroit intercepted a suspicious package — a white, legal-sized envelope with the words "Legal Documents Private and Confidential" written twice on one side. It had been en route from a UPS store in Toronto to a UPS store in Florida.

Inside were four pre-addressed, postage-paid letters and three sets of latex gloves. Two letters were addressed to Peerenboom's wife, Robin, at the couple's residences in Palm Beach and Toronto. Two others were addressed to employees of Mandrake.

The content of the letters was… familiar. They said that if Peerenboom didn't leave Palm Beach, the letter writer would send the earlier letters claiming Peerenboom was a child molester to prisoners across North America.

The U.S. Department of Homeland Security contacted federal authorities in Canada and discovered a man by the name of David Smith had mailed the package to himself, using an alias. Smith was a former employee of Mandrake, where he had worked for 14 years, rising to the rank of partner before starting his own headhunting company.

In court documents filed by Perlmutter as part of his defence against the slander accusations, Peerenboom is quoted as saying Smith was fired "after he was caught misappropriating Mandrake proprietary information ... [and] other misconduct at the firm." Peerenboom also said, according to the court documents, that Smith "may or may not be disgruntled."

Smith was investigated by Toronto police and, on June 22 of this year, was charged with extortion, forgery and criminal harassment — charges that were stayed three months later.

Smith's legal team did not reply when asked about the circumstances of his exit from Mandrake, but the former employee who was at the firm during his tenure said Smith and Peerenboom "were always butting heads." Smith himself would not speak with CBC when reached by phone.

The Perlmutters' lawyers contend the Smith letters exonerate their clients. "I believe that the events that have occurred involving David Smith show that Ike Perlmutter was not involved in sending these hate mail letters and that Mr. Peerenboom should now withdraw his slander suit and issue an apology to Mr. Perlmutter," Black said in an interview with CBC News.

In court documents filed by Perlmutter, his lawyers describe the Hebrew insults in the letters as an awkward attempt to frame their Israeli-born client and suggest that Smith's "efforts were so clumsy they could only possibly fool someone like Peerenboom who either wanted to be fooled or was in on the act." They cite reports that Peerenboom might have been willing to settle the matter for $400 million as evidence that it was all a scheme on Peerenboom's part to extort money from Perlmutter.

Peerenboom's legal team says the extortion claim is nonsense and has played down the significance of the Smith arrest, focusing instead on the admission of guilt by the Perlmutters with regard to the 2011 letters.

"Harold wouldn't go to the wall if he didn't believe he was right," said Peerenboom's former employee of his insistence on pursuing Perlmutter despite the charges against Smith.

The fact the charges were eventually stayed — at the direction of the Crown, according to court documents — makes matters even murkier.

Smith signed a $500 peace bond and was ordered to not have any contact, directly or indirectly, with Peerenboom; to keep the peace; and to be "of good behaviour, especially with regards to Harold Peerenboom."

Smith's and Peerenboom's lawyers didn't respond to questions about the most recent developments in the case, but Perlmutter's lawyer, Roy Black, expressed irritation with the Crown's decision to request a stay.

"I am surprised the Crown would take this action without asking for any input from Mr. Perlmutter, who is a victim of this scheme," Black wrote in an email.

Eriq Gardner, who has been covering the twists and turns of the case for the Hollywood Reporter, finds it all surreal.

"I keep thinking there's nothing more here that can stun me — and keep getting flabbergasted by every new development," he said.


The revelations about Smith certainly moved some suspicion away from the Perlmutters. But Peerenboom isn't the only one who received hateful letters and is looking to find the culprit.

William Matheson, president of the Sloan's Curve Homeowners Association, said he got a threatening letter in 2015 telling him to get out of the area. Matheson and his wife were among those who had raised questions about Donnelly's tenure at the tennis facility. The couple, along with Peerenboom, was named in Donnelly's original slander suit.

The content of the letters Matheson and other residents received left no question in his mind that the hate mail was sent by somebody living or working in Sloan's Curve. Matheson said he is not taking sides in the Peerenboom-Perlmutter battle — he just wants to see the matter resolved.

"I'm a born bully. My forefathers couldn't get along with anybody. I still can't."

"I don't think many of the owners here are partisan," he said. "I think they think the hate mail was vile and would like to see the person found out."

Peerenboom also seems to be hoping the case will eventually make it to trial. While his financial resources aren't quite on par with those of Ike Perlmutter, Peerenboom doesn't seem fazed by the prospect of adding to his already formidable legal costs.

"That wouldn't stop Harold from going after [Perlmutter]," said Judi McLeod, publisher of Canada Free Press. "That wouldn't stop him at all. He doesn't back down."

Lisa Raitt expressed similar sentiments. "I'd be surprised if he quit. That would surprise me. That would make me think, What's going on? Is Harold OK?"

It may just be in Peerenboom's DNA — this dogged sense of justice, the instinctual need to fight back. Perhaps Peerenboom himself put it best more than 40 years ago.

"I'm a born bully," he told the Toronto Star in 1975. "My forefathers couldn't get along with anybody. I still can't."

Editing: Andre Mayer and Kazi Stastna | Illustrations: Philip Street and Scott Galley