Inside Ottawa real estate pioneer John Ruddy’s lifetime of achievements

‘Visionary’ behind Lansdowne’s revival forged his reputation in business as a trailblazing retail developer, but it’s his passions for football and philanthropy that have left the most indelible mark on his community
2017 Lifetime Achievement Award recipient John Ruddy. (Photo by Mark Holleron)

The man who did more than perhaps anyone else to bring CFL football in Ottawa back from the dead can’t remember a time when the game wasn’t part of his life.

John Ruddy grew up the son of a former pro running back in a house a few doors down from Rough Rider hall of famer Bobby Simpson. When the family moved, their new neighbours included legendary coach Frank Clair.

Not surprisingly, the young man became a rabid fan of Ottawa’s CFL team that Mr. Clair was moulding into a perennial powerhouse led by quarterback Russ Jackson. But as surely as football was embedded in Mr. Ruddy’s DNA, so was business.

His father John Sr., a former star halfback with the Ottawa Trojans, eventually launched his own company selling home heating oil and installing mechanical systems in downtown office buildings. The seeds of his son’s future entrepreneurial success were planted right then and there.

“When (John Sr.) first started his business, his office was in the house,” Mr. Ruddy, 65, says during an interview at Trinity Development Group, the company he founded in 1992. “I lived it and breathed it. I was exposed to a business being built from the ground up. Obviously, that rubbed off on me.”

That’s an understatement. Thanks to its founder’s unrelenting drive – not to mention the keen eye for design Mr. Ruddy cultivated as an architecture student – Trinity has become a leading force in commercial real estate across the country.

A pioneer of big-box retail development in Canada, the company has built properties from the Maritimes to Alberta. When Mr. Ruddy sensed the market for big-box stores was reaching its saturation point, he began shifting Trinity’s focus to mixed-use projects such as Lansdowne. Today, the firm is at the forefront of a new wave of transit-oriented development with its ambitious plans for a trio of soaring highrises at Bayview Station near the intersection of the Trillium and Confederation LRT lines.

Mr. Ruddy’s business acumen, entrepreneurial vision and philanthropic generosity have earned him this year’s Ottawa Business Journal-Ottawa Chamber of Commerce Lifetime Achievement Award. He'll be recognized for his achievements at the Best Ottawa Business Awards gala on Wednesday, Nov. 15.

It's an honour his many friends agree he richly deserves.

“The guy’s done it all,” says Trinity CEO Fred Waks, who’s known Mr. Ruddy for more than 20 years. “And he’s done it all with a great sense of modesty and style. There’s not a finer human being that you’ll meet.”

Gruelling study

Still, a career in real estate was never a guarantee for Mr. Ruddy. After graduating from St. Patrick’s High School, where he made his own mark on the gridiron as a running back and linebacker, he went on to study architecture and play football at Carleton University.

The demands of those two pursuits make them a rare combo for a student-athlete. Mr. Ruddy’s teammate Barry Hobin, one of the few others to follow the same path and now one of Ottawa’s best-known architects, recalls the gruelling regimen: leaving class at 4:15 and going to football practice for two hours, then having dinner and heading back to the architecture building to toil in the studio until 11 p.m.

Mr. Ruddy believes that rigorous schedule helped give him the discipline to succeed in business later on.

“It’s a big load,” he says. “If you didn’t manage your time well, you wouldn’t make it.”

At 5-foot-10 and 180 pounds, Mr. Ruddy wasn’t the biggest or fastest of the football Ravens. That never stopped him from throwing his body around with reckless abandon from his spot in the defensive backfield.

Ruddy in his Raven days. (Photo provided.)

“If there was a collision, either he was going to get banged up or the other guy was,” says his longtime friend and former Raven teammate Terry Kiefl. “Typically, it would be the other guy that would get the worst of it. That was his game. He wasn’t a speed merchant, but he was smart and he hit hard.”

But that punishing style took its toll on Mr. Ruddy, who now has two artificial knees to show for it.

“It seemed like I spent every off-season in crutches hobbling around the campus,” he says with a rueful grin. “That kind of was my program: play football, then crutches.”

After graduating in 1975, he moved to Toronto, where he initially worked for an architecture firm and moonlighted as a bartender. He also bought and renovated a house, and the profit he made on its sale – three times his salary as an architect – convinced him real estate was the way to go.

“As a business model, it was more attractive to me to get into the development business as opposed to staying the course as an architect,” Mr. Ruddy explains. “It seemed like a natural thing at the time.”

He entered the business on the sales side, eventually spending 15 years with shopping mall developer Landawn. By the late 1980s, however, double-digit interest rates and a crippling global recession had left the industry in tatters. In 1992, Mr. Ruddy decided to pack up his young family and head home to Ottawa, where, as Mr. Hobin puts it, he started over at “ground zero” with a new venture he called Trinity.

At a time when real estate behemoths such as Olympia and York were toppling under mountains of debt, Mr. Ruddy perceived a shift in the retail landscape that would ultimately make him a fortune.

By the early ’90s, big-box retailers from the United States such as Walmart and Home Depot had begun looking to expand north of the border. Using the connections he’d made in Toronto with the likes of Kmart and Famous Players, Mr. Ruddy jumped at the chance to accommodate them. Soon, he was developing open-air malls from Calgary to Halifax.

“He was tenacious about building connections and making projects work when no one else was doing it,” Mr. Hobin says.

Looking back, Mr. Ruddy says he focused on fulfilling a market need while his competitors were fighting just to survive. In the past 25 years, Trinity has developed more than 25 million square feet of retail space, including major projects such as South Keys here in Ottawa.

‘The stars were aligned’

“That was at a time when real estate was a bad word,” he says. “A lot of major developers in Canada at the time went broke. Everybody thought I was crazy to get involved in the real estate business. But because it was a very difficult time in the business, it also created great opportunities. The stars were aligned, as they say.”

Mr. Ruddy’s rise to prominence prompted many in the community, including his own father, to suggest he was just the man to revive CFL football in Ottawa after the Rough Riders folded in 1996.

“I always pointed out to him, ‘You know what, dad, as a business model, it doesn’t really work,’” he says. “(Teams in Ottawa) all lose money and they go broke.”

“He’s a pioneer and he’s a visionary.”

But by the mid-2000s, after the demise of the city’s second CFL franchise, the Renegades, Mr. Ruddy sensed another change coming in real estate. Urban planners were encouraging developers to build downtown condos so people could live closer to their work, opening the door for mixed-use projects that combined housing, retail and commercial development.

Where many others looked at dilapidated Lansdowne Park and saw a financial sinkhole, Mr. Ruddy saw opportunity. He convinced fellow developers Bill Shenkman and Roger Greenberg as well as 67’s owner Jeff Hunt to partner with him to rebuild the crumbling football stadium and revitalize the surrounding area with shops, restaurants, office space and condos. John Pugh later joined the partnership that became the Ottawa Sports and Entertainment Group, bringing soccer into the mix.

More than just football

“We had to come up with a plan that was more than just about a date for nine games a year,” Mr. Ruddy says. “We had to look at it beyond just football.”

Eight years and more than few roadblocks later, the Redblacks made their CFL debut in 2014 at a completely remodelled TD Place stadium, where they’ve played to packed houses ever since.

“I know I would not have gotten involved in Lansdowne but for John’s involvement,” says Mr. Greenberg. “In my mind, John was always the centrepiece. He just had a gravitas to him and a sense of accomplishment.”

Mr. Greenberg, the executive chairman of the Minto Group, says his business partner combines “the passion of football” with “the intelligence and breadth of vision” of an architect and the skills of an entrepreneur.

“You put those combinations together, and he was able to craft … an opportunity that seemed to make a lot of sense to the rest of us.”

Ottawa lawyer Mark Wallace, who’s known Mr. Ruddy since they were kids, says the Lansdowne project epitomizes his friend’s dogged determination as well as his passion for building a better community.

“He had the vision to turn it into a multipurpose venue and also had the perseverance to see it through. When he decides he wants to get something done, he gets it done.”

“He had the vision to turn it into a multipurpose venue and also had the perseverance to see it through,” he says. “When he decides he wants to get something done, he gets it done.”

Although the Lansdowne project isn’t a money-maker yet by any stretch, Mr. Ruddy says he and his partners have never looked at it purely through a financial lens.

“We had a long, proud history of football in Ottawa and it was something that myself and my partners wanted to bring back,” he says. “I think people are proud of what we’ve done.”

With the Confederation LRT line on track to open next year, Mr. Ruddy is now turning his attention to projects strategically located near light-rail hubs. He’s a major partner in the group negotiating with the National Capital Commission to redevelop LeBreton Flats and build an NHL arena on the site. Just down the road at Bayview Station, Trinity is the lead investor in a $400-million plan to build the city’s three tallest mixed-use towers at the intersection of the Trillium and Confederation lines.

Mr. Ruddy believes transit-oriented development will be the next big thing in Ottawa real estate, and once again he wants to be at the front of the pack. Mr. Waks isn’t surprised his business partner was among the first to grasp the scope of the opportunity light rail presents.

“He’s a pioneer and he’s a visionary,” Mr. Waks says.


2017 Lifetime Achievement Award recipient John Ruddy. (Photo by Mark Holleron)

Generally a man who shuns the spotlight, Mr. Ruddy says he’d “rather be noticed by the things I do as opposed to the things I say.” The examples of his good work span the entire community.

Mr. Ruddy contributed $2.5 million of his own funds to help resurrect Carleton’s football team, which returned to the field in 2013 after a 15-year absence. Through his Trinity Development Foundation, he’s quietly donated millions of dollars to organizations such as the Ottawa Heart Institute, the NAC and the YMCA-YWCA. In 2015, he chaired a campaign that raised $25 million for the Royal Ottawa Foundation for Mental Health, kickstarting the fundraising drive with a $1-million gift of his own.

“What’s amazing with John is he does it all with such humility,” says Gordon Cudney, a member of the foundation’s board of directors who worked closely with Mr. Ruddy on that campaign. “It’s not about, ‘I need to have my name on this or that.’ It’s very quiet, understated, but he’s always there to support you.”

For Mr. Ruddy, health-care research, particularly in the field of mental illness, is a deeply personal cause. Two of his sisters took their own lives, Julia in 1983 and Christina in 2007. Another sister, Gina, died of cancer in 2013.

“Having firsthand experience of how difficult that can be for families, it was just a natural thing for me to help when I was called on,” he says of his role in the Royal Ottawa campaign. “Back in the ’80s, it was something you just didn’t discuss. Fortunately, we’re much more attentive to issues of mental health and it’s being recognized as a disease that can be managed, but we need more resources applied to it to get to where we ultimately want to get to.”

Varied interests

A man of varied interests, Mr. Ruddy enjoys travelling as well as music and art. Renowned for his loyalty to friends, he loves hanging out with his old buddies at Redblacks games and going on ski trips to Colorado with the boys.

“He’s still very much the same guy he always was,” says Mr. Kiefl, who first met Mr. Ruddy more than 50 years ago. “He’s an Ottawa guy that never forgot his roots and gives back to the community.”

These days, he splits his time among homes in Rothwell Heights, downtown Toronto and Sarasota, Fla. He and wife Jennifer have two daughters – Nikola, 26, and Sonya, 24 – who have followed in their dad’s footsteps and now work in commercial real estate in Manhattan.

His reputation as an industry trailblazer firmly established, Mr. Ruddy could ease into a blissful retirement and no one would begrudge him. But that’s just not his style.

“Quite frankly, I really enjoy this,” he says with a smile. “If I didn’t enjoy it, I wouldn’t continue to do it.”

And his hometown is a far better place because of it.