Brad Mills-Imagn Images
When we last spoke with Ted Leonsis in 2008, he was a relatively young fella – barely 50 and eager to check as many things as he could off his 101-item bucket list. He was up to No. 74 back then, and he’s since taken care of winning a pro-sports championship and having a net worth exceeding $1 billion. Space travel seemed a bit far-fetched at the time – not so much today.
But now that the Washington Capitals’ owner is nearly 70 and is armed with increased perspective and life experience, he’s no longer maniacally chasing the goals he set after a brush with death in his mid-20s. The only one he’s really intent on knocking off still is a hole in one. Might get it; might not. You know, golf.
These days, it’s less about an elaborate to-do list and more about the little things. Things like, well, toilet paper. When a Capital One Arena restroom runs out of it, even if it’s late in the third period, Leonsis insists it be instantly replaced. Leonsis has owned the Capitals for a quarter of a century and is one of the most powerful men on the NHL’s board of governors. The team he bought for $85 million in 1999 is now worth around $2 billion. After Jeremy Jacobs of the Boston Bruins, he is the fastest owner in NHL history to achieve 1,000 wins.
This is no faceless corporation or hedge fund. This is a man who is deeply passionate. Again with the toilet paper. “Don’t think you’re just replacing the toilet paper,” said Leonsis from his vacation home in Palm Beach, Fla., where he was flanked by replicas of the Stanley Cup his Capitals won in 2018 and the WNBA championship trophy the Washington Mystics captured a year later. “It protects the integrity of the organization and the team, but it also signals that we care. And the rest of the city is going to have to act this way.”
Yes, the Brooklyn native has become quite civic-minded when it comes to all things Washington, D.C., over the years. To him, the Caps aren’t simply a revenue-generator. They’re unifiers. They bring the city together. He always marvels at how Washington has more PhDs than any other city in the country and how there are more languages spoken there than anywhere. But once the puck drops, those denizens become a pack of glass-banging hockey zealots clad in red sweaters, the vast majority sporting the No. 8 and the name ‘Ovechkin’ emblazoned across the back.
When Leonsis bought the Caps in 1999, they were barely a blip on the sporting radar. Ovechkin has had a lot to do with the club’s rocket to relevance, but other owners have had superstar players and failed to capitalize on their appeal.
But Leonsis is no stranger to building. His first venture was a computing magazine called LIST, which he started with $1 million in seed money in 1981, then sold two years later to Reuters for $40 million. Leonsis was also one of the earliest leaders at AOL, a company that helped people log into this phenomenon known as the “internet,” and he was a key player in AOL becoming a multi-billion-dollar company. When the dotcom bust happened in the early part of this century, Leonsis was at the forefront of modernizing AOL and led its recovery, essentially building and rebuilding the company. It was spun out to Yahoo and a number of other entities and is now owned by Apollo Global Management. “They actually reached out to me,” Leonsis said. “And (AOL co-founder) Steve Case asked, ‘Do you want to buy it back?’ ”
“I want to win Cups. The most important thing is winning the championship because there’s no arguing, no calculating. It’s zero-sum.” – Ted Leonsis
That’s not happening as Leonsis has focused his efforts on his duties as the chairman of Monumental Sports & Entertainment, which owns the Capitals, Mystics and the NBA’s Wizards. Monumental Sports – the only sports entity in North America that owns multiple teams in the same market along with the building out of which it operates and the TV network that carries its games – is built to last, says its owner. “We’re not chasing shiny objects in soccer leagues in London,” Leonsis said. “We’re not trying to buy multiple teams in multiple markets. That, to me, is a financial play, not a fan-oriented, civic-oriented maneuver.”
After exploring building a new arena complex in Virginia, Leonsis opted to keep the teams at home in D.C. With about $500 million in government funds and $500 million of his own money ($200 million of which has already been invested), Leonsis has planned a three-year rebuild of Capital One Arena. Year 1 will focus on player amenities, Year 2 on the inner bowl and Year 3 on the exterior. A child of the 1960s, Leonsis has been inspired by the late poet and critic Ezra Pound. “His philosophy was ‘Make it New,’ ” Leonsis said. “Those were T-shirts that I gave everyone. You’ve got to make it so if someone goes there for the first time, they go, ‘This is a new arena.’ ”
What will never grow old for Leonsis is the pursuit of championships. Even he admits he’s come up a bit short on that bucket-list item. After a summer in which the Caps majorly revamped their roster, they once again look like contenders, with ‘Ovi’ defying all laws of time in his chase for Wayne Gretzky’s goal-scoring record.
Leonsis is thrilled he’s lasted 25 years and has built the team to be well-positioned for 25 more, but what he really wants is to see his name etched on the Stanley Cup a few more times. “We made all these announcements (when he won his 1,000th game), and I was flattered and humbled, but it didn’t mean a lot to me,” Leonsis said. “I was expecting it to mean more. Because I want to win more Cups. The most important thing is winning the championship because there’s no arguing, no calculating. It’s zero-sum.”
This article appeared in the Jan. 5, 2025, Money and Power issue of The Hockey News. In this edition, we feature a comprehensive dive into the business side of the hockey world, including a list of the top 100 people of power and influence from the world of hockey for 2025. Additionally, the issue contains features on the Tavares tax case, Q&As with hockey’s biggest powerbrokers and more.
It’s available on newsstands now, or you can get it in print for free when you subscribe to The Hockey News at THN.com/Free today. All subscriptions include complete access to more than 76 years of articles at The Hockey News Archive.
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