By any measure, Beate Moore was a stunner. Old black-and-white photographs from her modelling heyday depict a lithe figure that carried her to New York from Germany in the early 1960s to work for the famed Ford modelling agency. Her plan was to stay a few months before moving home, but love intervened.
She caught the eye and captured the affections of James (Jimmy) Moore, a young fashion photographer, whose images helped define the modish cool of the 1960s and 1970s and featured a gallery’s worth of famous subjects, from Cary Grant to Catherine Deneuve to the German woman he married. The couple raised their kids in the big city, but they moved to the Hamptons for a quieter life once the nest was empty.
“This really is a special place,” Moore said.
It is a place of extremes, of historic villages, family farms that have been passed down through the generations, beach day-trippers from New York hauling around their sunburnt kids, party animals, pickleballers and exorbitantly wealthy folks who shell out tens or even hundreds of millions of dollars to own a piece of Hamptons’ heaven in the priciest luxury real estate market in the Western Hemisphere.
Moore gets along just fine with the fancy neighbours except for the billionaire with the place to the north of her, who isn’t her cup of tea. The fellow planted a monster, scenic-view-killer of a hedge more than a decade ago, rankling her and others, although she now views the hedge as a blessing since it means she does not have to see him.
Said neighbour was also involved in an uncomfortably remembered legal scrape with the town of Southampton, N.Y., in which he filed multiple lawsuits at the state and federal court levels, suing the town and a number of individuals for a reported US$80-million combined, give or take. The fracas concerned the town denying his desire to build a giant barn and a basketball court on his 40.74-acre estate in an “agricultural overlay district,” according to court documents.
The parties eventually reached a settlement and as far as Moore is aware, the big barn never did get built, despite the neighbour being given the green light to do so.
“He is who he is,” she said.
Neighbours, of course, do not always get along, even in the most idyllic setting. But Moore’s tale of neighbourly frustration may feel familiar to Canadians, who have been experiencing their own run-in with the man behind the hedge, Howard Lutnick.
Lutnick emerged as a key figure in Donald Trump’s cast of trade war super villains with all the subtlety of a gut punch during a virtual appearance at the annual Canada-U.S. Summit hosted by BMO and Eurasia Group in Toronto in October 2025. The United States commerce secretary told the audience that the U.S. planned to dominate the auto sector and that Canada had better get used to the idea, according to the Toronto Star, since comparing the way things used to be to how things ultimately were going to be would lead to disappointment.
He popped up again in early June, days prior to the grand opening of the long-awaited, $6.4-billion, paid-for-by-Canada Gordie Howe International Bridge connecting Windsor, Ont., and Detroit, which subsequently did not open until late July. Bloomberg News reported sources said Lutnick “intervened” to delay the opening and was “pressing” to renegotiate the terms of the deal to give the U.S. a bigger cut of the bridge’s toll revenues.
August brought even more trouble, with Canada and the U.S. engaged in 11th-hour talks to try to head off a fresh round of 50 per cent tariffs. Reports swirled that Lutnick either did or, according to him, did not have a hand in dynamiting the discussions.
Prime Minister Mark Carney was asked directly whether Lutnick was an impediment to the deal during a press conference. He half-smiled and answered diplomatically, saying the Canadian negotiating team was “unified,” but he could not say the same “for the United States Administration.” Lutnick was later interviewed about the ruckus on Bloomberg Television. He blamed Team Carney for killing the talks for “political reasons.”
Things have only gotten worse since then. Insults have been flying, $27.6 billion in Canadian goods have been hit with those 50 per cent tariffs , more tariffs are on the horizon and a ban on Canadian imports of alcohol, motorcycles and other goods is slated to take effect on Sept. 29. Canada has responded with more or less dollar-for-dollar tariffs on select U.S. goods.
Publicly, Lutnick has said Canada’s trade strategy is “the worst,” lumped Canada in with the other countries that allegedly treat the U.S. like “crap” and accused Canadians of being cheaters on so-called free trade. His elbows up, outspoken, made-a-fortune-on-Wall-Street approach is no doubt grating to many Canadians, but when he isn’t courting controversy, his life story is also by turns sympathetic, impressive and even inspiring.
His parents died within 18 months of one another when he was a teenager. Layered on top of that tragedy was the reaction of his extended family that left him, his older sister and younger brother to fend for themselves.
“The way I describe it, you’re either in or you’re out,” he once told New York Magazine. “What I learned in 1979, all my relatives stepped out. We learned to live without all of them. All of them. It was just the three of us.”
A gifted athlete, he captained the varsity tennis team at Haverford College in Pennsylvania. His coach there, Marty Gilbert, once described him as having the tenacity of a “pit bull” and described him as a leader who “embodied every attribute a coach would want for his captain.”
Those qualities would serve him well when he arrived on Wall Street in 1983 as a new hire at Cantor Fitzgerald LP, a financial services company. By the age of 30, Lutnick was president and his slicked-back hair, scrappy New York City accent and hard-charging approach marked him as a Wall Street alpha. He certainly played to win and was mentored by firm founder Bernie Cantor.
He soon engaged in an ugly legal battle with his mentor’s wife for control of the company when Cantor’s health began to fail and he came out on top. One former Cantor Fitzgerald employee, who spoke on condition of anonymity because they still work in finance, described their former boss as an incredibly “complex individual.” He was “brash and hyper-aggressive” and a relentless salesman.
The former employee also said he could be sympathetic to a person’s needs and ask how he could help, but be equally caustic in giving an employee an expletive-laden earful.
No matter what room Lutnick walked in to, he carried himself as though he were the smartest person in it, but most intriguingly, according to the former employee, was that the various dimensions of his personality could all come to fore during a single conversation.
The Sept. 11, 2001, attacks introduced him to an audience beyond Wall Street. Cantor Fitzgerald lost 658 employees when the World Trade Centre’s north tower fell. Lutnick’s younger brother was among those killed. He was not at the office that morning, but he later sat for an interview with news anchor Connie Chung, weeping openly at several points.
He spoke of funerals, rebuilding the company and an obligation to care for the families of the dead, though he stopped paying the dead not long after the attacks. He has said the move was necessary to ensure Cantor Fitzgerald’s survival, but it still registered with a colossal public relations thud, one he later redressed by earmarking 25 per cent of Cantor’s profits for five years to the company’s relief fund for surviving family members. He personally contributed US$1 million to a pot that grew to US$180 million. Forbes magazine has recently pegged his personal fortune at US$7.3 billion.
In February 2003, he bought the place in the Hamptons for US$15.1 million and a few months later travelled north to Saint Andrews, N.B., to speak at an Investment Dealers Association of Canada conference. Joe Oliver, the association’s president, a former investment banker and future finance minister in prime minister Stephen Harper’s cabinet, said a few words about the enduring social, strategic and economic bond between Canada and the U.S., before ceding the floor to Lutnick.
The overarching mood was one of good neighbourliness and the investment banking crowd was there to get along. Lutnick said he was happy and excited to be in Canada.
“The Investment Dealers Association of Canada was incredibly supportive of our firm,” he said. “We were crushed with kindness, so that’s why I came.”
Originally scheduled to speak about electronic bond trading, Lutnick focused instead on 9/11, moving an audience of 185 influential investment movers and shakers to both tears and laughter.
“People were enthralled by his story; it is tragic, dramatic, and it speaks to resilience,” Oliver said. “Let’s face it, Lutnick is a tough guy. But he is in a different role now: he is MAGA.”
Trump, MAGA and the bulldog occupying the commerce secretary’s chair and making life difficult for Canada were all still a ways off when Carl Benincasa met Howard Lutnick in person for the first and only time in 2015. The now 46-year-old was Southampton’s town lawyer, but he was raised in Sag Harbor, a blue-collar Hamptons town lately gone upscale.
It is a transformation some residents welcome, while others pine for a return to bygone days. Lutnick, in nearby Bridgehampton, is symbolic of the transition, and he is not the only wealthy person who has had designs on building big things.
For example, circa 1970, Hamptons’ residents had an epiphany: they could either work to preserve agricultural land — some of the richest farmland in the U.S. — or else watch as the place got paved over into a giant subdivision for families with a ton of money.
Tracts of land designated as agricultural reserves were subject to certain restrictions as to what a property owner could and could not build upon them. Broadly speaking, it came down to whether whatever was being proposed had agricultural utility. Of course, good intentions don’t necessarily produce unambiguously worded land preservation documents.
The property Lutnick purchased in 2003 was among the town’s first agricultural reserves, formed in 1980. The town’s supervisor reportedly described it as “the worst ag reserve ever written” and open to differing interpretations.
Lutnick flew in by helicopter to meet with officials at Southhampton town hall to try to sort out a near-decade-long back-and-forth between the parties. He had a “crew with him,” Benincasa said, and an undeniable conviction that the barn and the basketball court were his to build — period.
“He was certainly a confident guy, and he was convinced of his position that he was in the right, and I don’t know that I would say he was compromising,” Benincasa said.
Now in private practice, he said a sizable chunk of the work he does involves agricultural reserves as well as other land parcels owned by wealthy people looking to assert their property rights while the town tries to limit what gets built. It is a constant tug of war that typically ends in some form of compromise, which sounds a lot like how international trade negotiations are meant to function.
But Lutnick didn’t need to give much in settling with the town. Once he reportedly had a permit in hand to build the barn, he was to abide by a five-year moratorium, during which he would refrain from applying for building permits related to non-agricultural and non-landscaping improvements outside of an agreed-upon building envelope. There were some additional fine points, but that was the end of it as far as anyone involved can remember.
“Do neighbours generally get along in the Hamptons? Generally, yes,” Benincasa said. “Of course, the instances you hear about are the ones where there is a problem.”
The same applies on the international stage. Lutnick does not have a problem blaming Canada for any number of things. He said the U.S. is being treated like “crap” by everybody during an exclusive Fox News interview in February 2025 and that free trade with Canada was not so free after all.
“They tax so many different things, lumber, they tax our food, it is outrageous,” he said. “They basically cheat around the side and then when we don’t act, they cheat right down the middle and the president is sick of it.”
He said tariffs were going to bring manufacturing back to the U.S., not overnight, but in time. Some on Wall Street might not like the idea, but he said this was about all Americans such as the auto workers in Ohio and Michigan and those in the steel industry in Pittsburgh.
Lutnick’s apparent transformation from business guy to tariff warrior harbouring a beef with Canada has been a curious development, according to the former Cantor Fitzgerald employee, since the boss he knew never expressed any disdain for Canada or Canadians or even adhered to any particular philosophy whatsoever. What made him tick, he said, was making boatloads of money.
Back in Bridgehampton, a former fashion model was discussing the finer points of luxury real estate. Moore’s photographer husband passed away in 2006 and she became a realtor who has brokered deals for homes that tick north of US$60 million. She knows she probably should not talk about such things, given her line of work, but said the Hamptons’ market is in rough shape.
Buyers are wary. There is a war in Iran, a trade war with Canada and enough uncertainty in the global economy to make even the wealthy think twice about spending a king’s ransom for a vacation property. The so-called trophy properties at the market’s highest end are still attracting interest, she said; otherwise, people seem content to play the waiting game.
“Properties aren’t flying off the shelf; people are concerned by what’s going on,” she said.
Moore has not had any Lutnick sightings lately, although her neighbour does have a reputation for hosting grand shindigs, including a fundraiser he and a couple of other bigwigs held for Trump in August 2024.
Some nights she sees car headlights peeking through the hedge.
“I don’t want to comment too much on him, but he is definitely still there,” Moore said. “Canada has always been such a great ally to us; what has been happening is terrible.”
• Email: joconnor@postmedia.com