Richest People

The Apostolopoulos family plans to build a mini-Vegas in Pickering, Ont.

This billionaire family is placing their biggest bet ever on a massive new entertainment complex, Durham Live

Steve Apostolopoulos standing in a cornfield

Steve Apostolopoulos standing on the site in Pickering, Ontario where his family hopes to build a $1.3 billion casino and entertainment complex. (Ryan Pfeiffer/Metroland)

At the corner of Church and Bayly streets in Pickering, Ont., sit 226 acres of grass, shrubs and a few clusters of trees next to Highway 401. It is a rare undeveloped patch of land in an area populated by low-slung strip malls and industrial buildings. The only structure on the site today is the Pickering Pentecostal Church. Soon, that humble house of prayer could be dwarfed by a sprawling tourist complex, anchored by a casino and a five-star hotel. The vision presented by the developer, the Apostolopoulos family from nearby Toronto, is akin to a mini Las Vegas. Kids will zip down slides at an indoor water park, or take in a movie at the 15-screen theatre. An open-air amphitheatre will host concerts during the warmer months, while a gleaming performing arts centre featuring an undulating glass facade could accommodate everything from symphony orchestras to comedians. Consumers will be drawn to the world-class retailers on site, and gourmet restaurants and pubs will be ready to feed the throngs of visitors. Across the street, the Apostolopoulos family plan to set up a movie and television production facility. (The Pentecostal church will remain at the southwestern end of the complex. “They nicely worked around us,” notes pastor Colin Gittens wryly.)

The proposed development is known as Durham Live, and it’s among the biggest real estate projects Pickering has ever seen—only the local nuclear plant is larger. It’s also the most significant development ever attempted by the Apostolopoulos family and their firm, Triple Group of Companies. The facility will bring in $600 million in total tax revenue and add more than $1 billion in GDP, according to an economic impact study commissioned by the company. “In the Greater Toronto Area, we thought there really wasn’t anything that could be considered a tourist destination that had the feel of a resort,” says Steve Apostolopoulos, son of company founder Andreas. (Steve’s two brothers, Jim and Pete, are also involved in the business.)

Durham Live would be an ambitious task for any developer. The price tag is at least $1.3 billion. Moreover, its successful completion requires support from the Ontario Lottery and Gaming Corporation, along with retailers and hotel chains. The Apostolopoulos family made their fortune by buying beaten-down buildings in undesirable areas, sprucing them up and filling them with tenants, primarily industrial and commercial users. It’s a low-profile and somewhat boring line of work. They’ve never done anything like Durham Live before.

The closest the family has come to this level of spectacle is their ownership of the Silverdome in Pontiac, Mich., the 82,000-seat stadium and former home of the Detroit Lions football team. When the family bought the Silverdome in 2009, their plan was to renovate the facility and attract a Major League Soccer franchise. It didn’t work out. The Silverdome has sat empty since 2013, becoming “a pitiful display of neglect and deterioration,” says Andy Meisner, treasurer for Oakland County, where Pontiac is located.

The derelict facility is an inauspicious monument to the family’s first foray into the world of sports and entertainment. But rather than retreat to their traditional line of business, the Apostolopoulos family is now attempting something even more ambitious. Maybe that’s hubris—unless it pays off.

It was the irresistible allure of a bargain that drew Andreas Apostolopoulos to the Silverdome. But that purchase is a cautionary tale of what can happen when a company steps outside its area of expertise. For those prone to reflection, it might hold lessons for how the Apostolopoulos family should approach Durham Live.

The stadium was built in 1975 for US$55.7 million at the peak of Detroit’s manufacturing might. It was home to the Detroit Lions and the Detroit Pistons, and hosted Pope John Paul II, Elvis Presley and Led Zeppelin. But Pontiac’s economy took a major hit as the auto industry declined. In 2002, when the Detroit Lions moved to another facility, the Silverdome was effectively shut down and remained empty for the next seven years.

By 2009, Pontiac’s finances were so dire the State of Michigan installed an emergency financial manager to stave off collapse. Pontiac owned the Silverdome, and the city spent $1.5 million every year just to keep it maintained. The financial manager felt the city urgently needed the Silverdome off its books and arranged an auction. Andreas participated by phone from Toronto. He offered $583,000. His was the winning bid.

Andreas Apostolopoulos always had a talent for watching every penny and had a keen business sense. He immigrated to Canada from Greece as a teenager in 1969, working in the kitchen at a Kentucky Fried Chicken before starting his own office-cleaning company, followed by a plastic bag manufacturing firm. Eventually, he got into real estate. Andreas has since amassed a large portfolio in and around Toronto. His company, Triple Group (named for his three sons), owns approximately 15 million square feet of industrial and commercial properties.

He and his sons promised to spend $50 million to renovate the neglected Silverdome facility and secure an MLS franchise (they’re big soccer fans), bringing jobs back to Pontiac and jolting the economyto life. But negotiations with MLS fizzled out. Pontiac isn’t much of a soccer town to start with. “He probably got in over his head,” says Leon Jukowski, a former Pontiac mayor. “Everybody was pulling for the right thing to happen, but the problem is, when you get somebody who doesn’t understand this particular market, they’re going to have a rough row to hoe.”

The family did organize events such as boxing matches at the Silverdome, but in January 2013, the stadium’s iconic white inflatable roof developed a tear. As ice and snow piled on top of the structure, the roof gave way, and fragments of fabric were strewn around the stadium. The optimism surrounding the Silverdome quietly died. The next year, the family decided to auction off whatever was salvageable. Nearly everything of value was put on the block—the scoreboard, the seats, the turf, even the urinals. The copper wiring reportedly brought in $77,500.

Meanwhile, Pontiac wondered about the Apostolopouloses’ plans for the Silverdome. In January 2014, a new mayor, Deirdre Waterman, was elected. Reaching out to the company was one of her first acts of office. Arranging a meeting with Andreas was difficult owing to his schedule, and they sat down in May or June, she recalls. “It was just a perfunctory meeting,” Waterman says. “He indicated his original hope to have a soccer franchise did not pan out, and he did not have an alternative at that time.”

For some, the Silverdome became an eyesore. A local group called Citizens Against Blight took aim at the Apostolopoulos family. Mona Hofmeister, one of its founders, had a successful track record of pushing city officials to demolish dilapidated foreclosed homes and undertook a similar strategy with the Silverdome, urging the company to tear it down or fix it up. Her letters went unacknowledged, however. “It’s like a stab in the heart, because we’ve been working so hard to clean up the blight in Pontiac,” Hofmeister says.

The Apostolopoulos family opted not to repair the roof, and as the stadium was left exposed to the elements, its condition worsened. They did, however, allow a Red Bull–sponsored BMX biker to film a promotional video inside the Silverdome; the rider performed tricks on its decrepit field and waterlogged stands. Fabric from the roof was still scattered around the interior, the turf was torn up and some of the seats were smashed and piled on top of one another.

Despite appearances, the Triple Group was not interested in letting the stadium rot indefinitely. Back in February, it announced a design competition to reinvent the Silverdome, allotting $4,500 in prize money. A website set up for the competition states Triple Group is seeking “outstanding ideas that will redefine the site.” The competition raised eyebrows in Pontiac. “I thought that contest was ridiculous,” says Meisner, the county treasurer. “I took that as an admission that they had no real plans of their own.”

But in June the company retained CBRE Group to market the property for sale, lease or development opportunities. The total value? Thirty million—even without a roof. Media reported that the entire 127-acre site was up for sale, but Apostolopoulos says that was never the case. Only parcels were being offered, he says. In late October, nearly three years after the Silverdome’s roof was destroyed and its guts auctioned off, the Apostolopoulos family released a redevelopment plan for the site.

The proposal allots 1.25 million square feet for light manufacturing spread across four different buildings; a retail and entertainment complex; restaurants; and mid-rise housing—but no Silverdome. The stadium will be demolished next year. The plan is still uncertain to some degree, and executing it depends on securing tenants. CBRE is still marketing the property to prospective users and developers. (It might be an easier sell now that the Apostolopoulos family has agreed to pay for the $3-million demolition of the Silverdome themselves.) Apostolopoulos says they’re already talking with two potential tenants.

He’s not particularly keen to talk about the past, however. As for why the family decided not to repair the roof and left the Silverdome to fester to the consternation of Pontiac, he doesn’t have much to say. “You could just say we were evaluating,” he offers. Any discussions they had with potential business partners during that time were confidential, making it difficult to comment publicly. He also disagrees with the notion that the family’s initial plan didn’t work out because they didn’t understand the local market. “We didn’t misjudge anything. We were very calculated,” he says. “We determined there was a bigger market for something else.” What happened, Apostolopoulos explains, is that the manufacturing sector in the region started rebounding, which opened up a new opportunity to provide industrial buildings for companies looking to expand operations. They didn’t get anything wrong; they just shifted course.

Meisner, who opposed the hasty Silverdome auction from the start, is supportive of the demolition plan. “Starting fresh will hopefully allow the marketplace to contemplate a new future for the site without the visual of a rotting, decaying, relic,” he says. But he’s less enthusiastic that Triple Group is still driving the process: “I’m trying to generate some cautious optimism.”

Artists rendering of the proposed Durham Live complex

An artists’ rendering of the proposed Durham Live entertainment and casino complex. (Triple Group)

Durham Live is a completely different project than the Silverdome, Apostolopoulos explains. With the latter, he inherited a troublesome building. Durham Live can be built from scratch. “Pontiac is a much different market than we have in the GTA,” he adds. “There is huge demand for this type of entertainment in the GTA. Pontiac is much more challenging.”

The scale of Durham Live is staggering: 200,000 square feet of gaming, 1,250 rooms at three different hotel concepts and about one million square feet of office space, plus nature trails. Apostolopoulos concedes there is already shopping, entertainment and gaming in the area, but he says Durham Live will have everything on one site. That will encourage families to book a hotel room and stay for a few days at the complex. “You could spend a day at the water park, and the next day, the family could do the casino. There will be daycare and children’s activities there,” he says. So far, the city is on board. During a municipal election last year, residents were asked in a referendum if they would support a casino in the city as part of a “hotel, convention centre, [and] entertainment complex.” Roughly 60% were in favour. Pickering city council also rezoned the land slated for development as a “major tourist destination,” and Apostolopoulos is optimistic about breaking ground next year.

But the casino component depends on the OLG. The gaming commission has allotted capacity for one casino in the region, and Durham Live is not the only proposal. A slots facility already exists at a racetrack in neighbouring Ajax, and its owners have put forward their own proposal to the OLG, albeit a more modest one.

Although Durham Live promises to create jobs and drive tourism, it’s by no means a guaranteed win, says an insider who works in entertainment and real estate in the region. (This individual asked to remain anonymous since it’s a small industry.) Because Ajax already has slots, expanding that facility might prove faster, easier and safer than going with an ambitious development that doesn’t yet exist. If Durham Live had partners lined up—Live Nation to operate the amphitheatre, for example—that might sway the OLG. None have been announced yet, but Apostolopoulos says it’s only a matter of time before deals are finalized. There’s also the small fact that the Apostolopoulos family hasn’t developed a casino or an entertainment complex before. As successful as they’ve been with industrial and commercial real estate, Durham Live is different. (Apostolopoulos says if the OLG decides to situate the casino elsewhere, Durham Live will still go ahead on a smaller scale.)

And then there’s the financial risk to the family itself. According to Apostolopoulos, they will fund the construction themselves through a mix of equity and debt. “Not a single dollar of public money will be in this deal,” he says, adding he’s comfortable with the level of debt that could be assumed. The financial burden could still be significant if the facility isn’t able to attract enough visitors. “It’s hard to get people to drive out for something if you don’t have a critical mass,” says the insider. “It takes time to build that destination.”

Apostolopoulos is confident Durham Live will be a draw, given its proximity to Toronto and its location next to the 401 and a GO Transit route. “All of our studies have indicated that it is viable,” he says. Even pastor Gittens at the Pentecostal Church can see the reason for developing the site. “That’s a prime spot that you can do a lot of fun stuff with,” he says. (Gittens—who, for the record, is morally opposed to the casino—does note the strangeness of having his church located “just about in the middle of this diabolic scene.”)

The company anticipates Durham Live will attract up to 14 million visitors a year. Visitors to Durham Live will come from within a 400-kilometre radius, the company says. That’s nearly as far north as Sudbury, Ont., and as far south as Pontiac, where the Silverdome awaits redevelopment. Despite the proximity, the Silverdome and its recent troubles are not on the minds of Pickering’s politicians. “I don’t know anything about the Silverdome,” says councillor David Pickles, who’s been an active supporter of Durham Live. “Everything the Apostolopoulos family have told us they were going to do, they’ve done. We have confidence in them, and we look forward to a very successful development.”

That goes for the Apostolopoulos family, too. Having amassed a fortune renovating old buildings, they now have the chance to build something from the ground up.