The Louisville native walked away from a career in medical sales after graduating from the University of Kentucky, choosing instead to pursue a new opportunity teaching pickleball in South Carolina. At the time, there was no guaranteed roadmap—just a chance to explore where the sport could take him.
Key highlights
- Casey Diamond left a medical sales career after graduating from the University of Kentucky to pursue professional pickleball.
- After years of battling through qualifiers and financial struggles, Diamond's career took off with improved results and international competition.
- A behind-the-back winner in his Major League Pickleball debut went viral and earned him two appearances on SportsCenter's Top 10 Plays.
- Diamond believes pickleball's rapid growth is creating greater opportunities for professional players through sponsorships and worldwide exposure.
“I would say it would be hard to tell you right now that I thought that I’d be where I am today,” Diamond said during a recent interview with WLKY News Louisville. What started as a career change soon evolved into something much bigger after he began connecting with established players in the sport. “Then I started meeting some local pros, and that’s kind of how it all started.”
Early struggles made the breakthrough even sweeter
Diamond's path to professional pickleball success was far from easy. In the beginning, he travelled from tournament to tournament, battling through qualifying rounds while struggling to earn enough money to support himself. “I was going through qualifiers at every event, not making any money, barely paying rent, all this stuff.”
His persistence eventually began to pay off as his performances improved and new opportunities emerged. “Then it kind of transitioned to winning more matches, winning goals, traveling all over the world. That’s it right there.”
One viral shot changed everything
Diamond believes a single defining moment transformed his career. “We’ve always talked about like one shot, one video, one match could change a lot, but it really, really did.”
That moment came during his Major League Pickleball debut, when he produced a spectacular behind-the-back winner into the corner. The incredible shot quickly went viral and earned him not one, but two appearances on SportsCenter's Top 10 Plays.
Initially shown during the early hours, the highlight continued to gain momentum. “The next day I turn on my TV when I got home, and it was number six.” The reaction from fans across Kentucky made the experience even more memorable. “It was just cool to see people text me like, 'I was watching at a bar, I was watching at a pickleball complex in Lexington'… all over Kentucky and just texting me and saying they saw this. It was awesome.”
The viral moment significantly expanded Diamond's profile, bringing him a larger fanbase and a growing social media following. “Most of my last name, that’s kind of what everyone comments on my social media. The diamond emoji and stuff, which is cool.”
Diamond's rise reflects pickleball's rapid growth
Diamond's journey has unfolded alongside pickleball's remarkable rise in popularity, with the sport creating more opportunities than ever before for professional players.
He pointed to the increasing involvement of major global brands as evidence of the sport's continued growth. “It’s crazy. Now you have athletes getting sponsored by Nike and these big, huge companies. No matter if I’m getting sponsored by them or someone else is, it’s just good for all the pro players.”
From struggling to pay rent while chasing tournament opportunities to becoming one of pickleball's emerging stars, Diamond's story highlights how quickly fortunes can change—and how one unforgettable moment can reshape an entire career. For Diamond, however, the journey is only just beginning.
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