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Vancouver House, a 52-storey residential tower under construction, is seen in Vancouver in March, 2018.  

Rafal Gerszak/Globe and Mail

Ian Gillespie had a problem: a piece of land the shape of a triangle.

It was 2010, and he was already an established developer. A few years earlier, his company, Westbank, had built Vancouver’s tallest tower, the 62-storey Shangri-La, and redeveloped the historic Woodward’s site in the city’s hardscrabble Downtown Eastside. But this property posed a new challenge. It was an awkward piece of land, wedged alongside an on-ramp to the Granville Street Bridge. The area surrounding it was shabby – home to several old, squat buildings. But as Mr. Gillespie mulled the lot, still unsure what he wanted to do with it, he recognized its potential.

“A lot of people would look at this site and say, ‘Okay, it’s a weird area,' " Mr. Gillespie recalled. “I looked at it as this tremendous opportunity, this gateway into Vancouver.”

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Mr. Gillespie had recently met Bjarke Ingels, a 36-year-old Danish architect who wasn’t widely known, but who shared the developer’s urge to create innovative projects. The two men discovered in each other kindred spirits. “From now on,” Mr. Gillespie told the architect, “I only want to build great buildings.” Soon after, Mr. Gillespie handed Mr. Ingels his triangular riddle.

Mr. Ingels took on the design problem and came back with something unusual. He’d imagined a luxury condo tower that began from a triangular base and, floor by floor, twisted into a rectangle. Even on paper, the structure seemed to taunt gravity and defy physics. Mr. Gillespie had found the answer to his puzzle.

Today, as construction at the site bangs, rattles and buzzes, the building dubbed Vancouver House has risen high above the bridge. It’s set to open next year and has already won a major international architecture award. Judges at the World Architectural Festival in 2015 called the eye-popping design a “delightful project” that will have a positive impact on “municipality- and developer-led agendas for cities across the world.”

Vancouver House is a statement building, a structure that flouts conventional expectations, but as an Ian Gillespie project, it’s not unusual. The developer revels in creating buildings that break the mould in surprising ways, typically through innovative, visually arresting design. His aim, he said, is to “really stretch the boundaries of what’s possible,” and he’s busy applying that trademark approach to a handful of marquee sites currently under development in Toronto, Vancouver and Seattle. With a portfolio of projects in the works collectively worth more than $10-billion – including another twisty tower in Calgary, a peaked condo complex in Toronto that mimics a mountain range (both by Mr. Ingels) and a development on the old site of the city’s landmark discount store, Honest Ed’s – the 56-year-old developer ranks as one of Canada’s most active builders.

Housing advocates in Vancouver have railed against his luxurious buildings, calling them magnets for high-end real estate market speculators that do little to address the city’s housing crisis – though a new affordable rental housing project Mr. Gillespie has pitched to the federal government could prove his critics wrong. In his quest to create buildings that grab attention, Mr. Gillespie makes no pretense of humility. Architecture in Toronto, in particular, is a “plague of ordinary,” he said. And with several developments under way in the city’s core, he’s resolved to change that.

“Unbelievable ambition”

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Ian Gillespie, shown training at UBC in 1982, was an elite 800-metre runner in his early 20s. Guided by coach Doug Clement, a former Olympic runner, Mr. Gillespie nearly made the 1984 Summer Olympics.

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Ian Gillespie has always been determined to stand out. In high school, he was a promising middle-distance runner and came into the orbit of Doug and Diane Clement, Olympians in the 1950s. Under the guidance of his new coaches, he got faster and faster on the track, but he was hampered by anterior compartment syndrome – a painful condition that caused swelling in the calf muscles, and required two surgeries. At the 800-metre race to make the Canadian team for the 1984 Olympics, Mr. Gillespie finished third and didn’t make the cut.

“Ian learned the bitter lessons,” Mr. Clement said. “He was quiet and reserved, but on the inside he had unbelievable ambition.”

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By then, he was in his early 20s and beginning to contemplate a new dream: a career in business. He wanted to be a millionaire by 30. As a teenager, he had been wowed by an older cousin’s 1972 red Jaguar E-Type convertible. Later, during his MBA at the University of Toronto, he considered investment banking, the 1980s siren song for many, but instead joined a real estate firm run by his cousin, Rod Schroeder, the man with the Jag.

It was not glamorous work: Schroeder Properties mainly developed strip malls. Over time, Mr. Gillespie’s relationship with his cousin became strained, and he started running projects by himself. By the early 1990s, now in his 30s and bored of working on shopping centres, Mr. Gillespie struck out on his own.

His first project was an office-residential-retail development in the suburbs. Mr. Gillespie was drawn to the challenge of developing a complex mix of uses for the site, and projects like this became a hallmark of Westbank’s approach.

As he continued to develop mixed-use buildings, Mr. Gillespie looked to James Cheng for aesthetic direction. The Canadian architect had been mentored by two greats in the field, American Richard Meier and Vancouver’s Arthur Erickson. Mr. Cheng was known for his slender towers that rose above a podium of townhomes – a style that came to define the city and become known as Vancouverism.

In the mid-1990s, the two collaborated on Westbank’s first project in downtown Vancouver. The development, called the Palisades, was a pair of oval-shaped towers. Mr. Cheng and Mr. Gillespie continued to work closely together into the 2000s, including on the city’s Shangri-La.

Starting with that tower, Mr. Gillespie also forged a financial relationship with Vancouver-based Peterson Group, which became his company’s go-to partner for several years. Mr. Gillespie and Ben Yeung, the head of the Peterson Group, sketched out their first deal on a Tim Hortons napkin.

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As he built these shiny high-rises, Mr. Gillespie saw he could use brand-name architecture, such as Mr. Cheng’s work, to sell expensive real estate. (Penthouses at the Palisades sold for $1.5-million, while two-bedroom units went for as much as $405,000, prices that seem low for the city by today’s standards but were high end in the mid-1990s.) The concept was new at the time in Vancouver, and became the second hallmark of Westbank.

“What we’re doing now, it’ll change Toronto”

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Developer Ian Gillespie, left, and architect Bjarke Ingels, in 2014. Mr. Ingels is behind everything from a headquarters and other offices for Google to geodesic domes in the desert outside Dubai, an experiment for human habitation of Mars.

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Mr. Gillespie made his debut in Toronto in 2012, with the sleek Shangri-La designed by Mr. Cheng, four years after Vancouver’s opened. At 67 storeys, the hotel-condo tower on University Avenue is one of the tallest in the city. (When construction started in 2007, the building was set to be Toronto’s highest residential tower.) The narrow high-rise climbs above two three-storey glass cubes. One houses New York chef David Chang’s Momofuku restaurants. The entrance features a striking stainless steel sculpture by Zhang Huan, one of China’s most influential contemporary artists. The display – a flock of birds lifting from a frame that evokes a dragon with twisting tree branches for limbs – cost more than $20-million to make, ship and install.

Now, he has three projects publicly under development in Toronto, including a new office-residential tower that Thomson Reuters plans to move into, condos on King Street and the buildings on the Honest Ed’s site, as well as several more in the works behind the scenes.

“When people see … what we’re doing now, it’ll change Toronto,” Mr. Gillespie said in an interview in his office on the Vancouver harbour. Dressed in dark jeans, a dark blue collared shirt and white laceless sneakers, he has a lean runner’s build, a youthful swoop of hair and greying stubble. His preferred soundtrack is old Bob Dylan albums playing faintly. He likewise makes his big statements in a soft voice, an expansive view of the North Shore Mountains behind him. “People won’t accept as much ordinary any more,” he said, as Maggie’s Farm plays.

It’s his partnership with Mr. Ingels that he hopes will cement his reputation as a visionary who offers the antidote to a bland cityscape. At 43, Mr. Ingels now ranks among the world’s hottest architects. The Dane is behind everything from a headquarters and other offices for Google to geodesic domes in the desert outside Dubai, an experiment for human habitation of Mars. Last fall, after Mr. Gillespie and Mr. Ingels met up in Toronto and were parting ways, Mr. Ingels joked: “I’m so over Earth.”

The pair plan to bring that ethos – to give the world something it has not yet seen – to Toronto’s King West. “Ian is a dynamic, aggressive, competent business person,” Mr. Ingels said. “But the driving force behind this is an almost childlike enthusiasm for buildings, and for ideas that make up those buildings.”

The project, however, a block from the corner of King Street and Spadina Avenue, is where they have run into the most trouble.

Mr. Gillespie had long been fascinated by the iconic Habitat 67 complex by architect Moshe Safdie in Montreal, a series of interconnected concrete apartments designed for Expo 67. So, for King Street, Mr. Ingels delivered similar terraced condos that climb to several peaks, none greater than 20 storeys, with trees on numerous balconies, like a forest. The new building was a stark contrast to the brick below. A courtyard would allow people to move easily through the site.

While the 2016 plan impressed observers, it ran against conventional thinking around heritage sites: Mr. Ingels had designed concrete cubes that sat directly on top of the existing brick structures. The traditional approach would have been to construct a simple tower set behind the old buildings.

After the first plan was submitted, Westbank and the city went back and forth, with the city trying to get the developer and Mr. Ingels to move the cubes off the brick buildings, among other things. Mr. Ingels said most developers would have given up, though it helped that the community liked the proposal. Last fall, a modified version of the initial plan was submitted and received approval in principle this month (Marketing for the condos begins in October.) The cubes will not sit right on top of the heritage buildings below. They appear to float above them – and the façade is glass blocks, rather than concrete. The number of peaks has been cut to four from five, reducing the number of units by one-fifth.

“The vast majority of developers are extremely conservative,” said former Toronto chief planner Jennifer Keesmaat, who had worked with Mr. Gillespie on his affordable housing project before deciding to run for mayor. “Ian is unique because he’s not.”

“Ian is trying to create things that will stand the test of time,” said Michael Emory, CEO of Allied Properties REIT, Westbank’s partner on King Street and elsewhere. “People value design. People aren’t racing through the city in their cars. They’re walking. They’re biking. They experience a building’s design.”

Seeking approval from the city on the design was “combative” in the words of Allied, and “difficult” in the words of Ms. Keesmaat. RBC Capital Markets has said the architecture was “innovative and edgy” but predicted approval could be a grinding process, because “innovative architecture often requires an acclimatization period.”

“A lot of people feel it’s not their city any more”

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Mr. Gillespie has expanded his reach in Asia and has two projects under development in Tokyo with architect Kengo Kuma, who designed the 2020 Olympic stadium.  

Rafal Gerszak/Globe and Mail

Six mannequins stand near the entrance of the Westbank office in Vancouver. They display vintage couture dresses. One is from 1965 by Yves Saint Laurent, a short white number inspired by painter Piet Mondrian. Near the end is an opulent ankle-length red dress with a flowing boa by Hubert de Givenchy from 1988, the same as the one worn by Mr. Givenchy’s muse Audrey Hepburn. In a few years, Mr. Gillespie said he could have one of the world’s largest vintage couture collections.

Alongside the art installations and buildings, Mr. Gillespie often puts his vision on display in ways other developers do not: He has published books and organized exhibitions to chronicle Westbank’s work. The first 500-plus page tome, released in 2012, was titled Building Artistry. The latest, at more than 600 pages, is Fight for Beauty. Its cover features a ballet dancer in Alexander McQueen’s 2003 shipwreck dress, one Mr. Gillespie described as intoxicating. Musicians are a staple, several times daily, at one of his Vancouver buildings, the Fairmont Pacific Rim, which he co-owns with Peterson Group. (The hotel has also served as the venue for a political fundraiser he hosted last November for Prime Minister Justin Trudeau. Mr. Gillespie publicly described himself as a “huge supporter” of the Liberal Leader at a December event he hosted there for Mr. Trudeau’s mother, Margaret.)

Last fall, the developer built an exhibition pavilion between his Shaw Tower and Pacific Rim buildings in Vancouver to showcase his work, blanketing the city with magenta advertising for the exhibit, which doubled as ads for the company. Westbank opens a new exhibition in Toronto on King Street on Sept. 13, to showcase its work with Mr. Ingels.

At a time when housing prices are spiralling upward, the self-promotion in Vancouver seemed out of touch. The campaign, also called Fight for Beauty, had a “Monty Burns-esque kind of feel,” said Andy Yan, citing the billionaire Simpsons character, who lords over Springfield from the nuclear power plant. In the minds of many frustrated city dwellers, Mr. Gillespie’s emphasis on high-end aesthetics over more affordable, serviceable buildings is the reason they can no longer afford to live in Vancouver. In Westbank’s latest development in the city, prices start at about $1-million for 500 square feet. The condo tower named Butterfly was designed by celebrated local architect Bing Thom, who died in 2016.

“A lot of people feel it’s not their city any more,” said Mr. Yan, the director of the city program at Simon Fraser University.

Web developer and civic activist Melody Ma created a parody website, skewering Westbank for raising housing prices upmarket and pushing out local residents. Dubbed “the Real Fight for Beauty,” the project cites local artists who say it’s in fact the luxury condos built by Westbank that have created a city with “no room for artists.” More than a hundred local artists signed an open letter of protest against the developer, saying he “treats housing as an elite commodity.”

Still, for all his focus on beauty, Mr. Gillespie has taken on projects that don’t rely only on aesthetics to make bold statements. In Toronto, he jumped at the chance to redevelop the prominent Honest Ed’s site, for which Westbank paid $72-million in 2013. (For Honest Ed’s, as well as both Shangri-Las, Westbank again partnered with Peterson Group.) The project – which includes a planned community of buildings with 800 rental apartments – doesn’t necessarily break the mould in terms of design like Mr. Gillespie’s other ventures, but it’s sure to leave a mark on the city because of its historic location on Bloor and Bathurst Streets.

A decade ago, he took on the redevelopment of Vancouver’s historic Woodward’s building because of the unique challenges the high-profile project posed. It wasn’t glamorous, but the major redevelopment would dramatically change the battered Downtown Eastside neighbourhood. It meant that the eyes of the city would be watching.

Westbank’s $375-million development was one of the largest mixed-use projects in Vancouver. It comprised 536 market-price condos and 200 units of affordable housing, two-thirds of those for people living with issues such as mental illness and drug addiction. The new complex has offices, a grocery and drugstore, as well as a new addition to Simon Fraser University’s Vancouver campus.

For Mr. Gillespie, taking on these projects is in part an attempt to alter his reputation: He doesn’t want to be seen as a real estate developer, but a “city builder.” His latest venture in this area is the Creative Housing Society, an independent non-profit group that he created last October.

In the winter, the group pitched the federal government on a plan to build 50,000 units of affordable rental housing, primarily in Toronto and Vancouver. The concept was valued at as much as $14-billion and could have fit in with Ottawa’s national housing strategy. But the idea hasn’t taken off.

Creative Housing wanted to leverage private capital with government support. Ms. Keesmaat was signed on as CEO in March – but in late July she made a surprise move to run for mayor of Toronto instead.

Creative Housing’s equity would come from an investor such as a large pension plan. Westbank and Allied Properties would also contribute capital. The Canadian Mortgage and Housing Corp. would be a linchpin, as the primary lender. Prospects looked good as Ottawa in February allocated $1.35-billion of new money over the next several years for “building more rental housing for Canadian families.”

Still, the process has been slower than Mr. Gillespie had hoped, as talks for low-cost loans from Ottawa and land from cities grinds on. A dozen projects are under discussion. Mr. Gillespie expects at least one will move forward by the end of the year. “It frustrates me,” he said.

But even as Mr. Gillespie works to make Creative Housing happen, he wants this project specifically to stand alone, saying he doesn’t want it to be “the Ian show.”

A global city

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At Vancouver House, about one-third of the units were sold outside of Canada, largely to Asian buyers. Mr. Gillespie brushes away criticism around this. In his view, Vancouver is a global city, one quickly changing with immigration.  

Rafal Gerszak/Globe and Mail

One line of attack Mr. Gillespie won’t apologize for is the amount of foreign capital his buildings have attracted. At Vancouver House, for example, about one-third of the units were sold outside of Canada, largely to Asian buyers. The developer brushes away criticism around this. In his view, Vancouver is a global city, one quickly changing with immigration, as well as investment from buyers living outside the country. For him, the bigger trend of immigration points in one clear direction. “We are going to become an increasingly Asian country,” he said.

Mr. Gillespie has expanded his reach in Asia and has two projects under development in Tokyo with architect Kengo Kuma, who designed the 2020 Olympic stadium. Westbank and Peterson Group are also working on a condo tower with Mr. Kuma in Vancouver.

Westbank has offices in Tokyo, Hong Kong, Shanghai, Beijing and Taipei – mostly used to sell expensive condos in Canadian cities. Mr. Gillespie has long seen buyers from Asia as important to his business. In his 2012 book, Building Artistry, he wrote of this business strategy that he has a “strong belief the future of our firm would be directly connected to growth in China.”

But no matter where the developer works, his obsession with leaving a lasting impression endures.

“It’s about giving me a canvas to produce something I feel good about producing,” he said. “It’s not just about beautiful buildings and great architecture. It’s about making cities more beautiful. Let’s look back in a hundred years and see which buildings made a lasting, positive contribution.”