You'd be hard-pressed to find a bigger Katie Ledecky cheerleader than Leonsis. His Twitter account is filled with links to stories about her, though it wasn't until right before the 2012 London Olympics that he realized how great she was going to be.
"In talking to Jon, talking to her mom, they all had this level of confidence that she hadn't reached any of her potential and that her upside was just so enormous and that the strides she was making were exponential, if you will, almost like month by month, year by year," Leonsis said. "And the one thing that they always said was that her fortitude and drive to be great was the best."
Around that time, Leonsis hosted another swimmer from Maryland, record-setting Olympian Michael Phelps, at a Wizards game and asked if he knew his family friend who had just qualified for the London Games.
"And Michael said, 'I'm sorry I don't, but I will look for her because that's terrific,'" Leonsis said. "Katie snuck up on everyone and exploded on the scene and won by a really, really big margin. And a year later Michael came to a Caps game and I said to him, 'Hey did you ever say hi to Katie and are you following her? Do you know who she is now?' And he had this big smile and said, 'She's awesome. She's a stud. I love watching her swim.'"
Katie was 15 at the London Olympics when she won the 800-meter freestyle by more than four seconds. Between then and 2016 she set world records in the 400-meter, 800-meter and 1,500-meter freestyle.
She also delivered a presentation about her experiences as an athlete during Leonsis' pitch to bring the 2024 Olympics to Washington two years ago.
"We flew [to San Francisco] together and flew back," Leonsis said. "And her ability to be a regular kid, student and a world-class athlete and the way she presented the authenticity, honesty, she did her own presentation and it was really special to see. I think Katie, as I've said, is one in a billion, not one in a million."
Heading into the 2016 Olympics, Leonsis was concerned about the level of expectation being placed on her.
"The announcers were saying, 'Katie Ledecky and everyone else,'" he said. "But these are the world's best at what they do. She won that race (the 400-meter freestyle) five seconds ahead of everyone, and then everybody was within half a second of one another. She's just reached this different plane right now and we forget how young she is."