Before every tournament, John Daly would open his closet and contemplate what to wear. Among the 300 pairs of extravagant (read: eccentric) pants he owned, the veteran would choose just about anything because “you’re pretty much going to match any shirt.” The hidden metaphor would be he’d eventually even match his caddie Anna Cladakis, too. Don’t be mistaken. Anna’s personal style was far from her player’s “shagadelic” style complete with loud patterns and dazzling colors. Instead, she’d resort to such golfing fashion faux pas moments for just one purpose: To make it easier for Daly to find her. And, that’s all you need to know to guess the kind of person Anna is.

Ever since the pair met in 2007—thanks to the golfing veteran’s Hooters endorsement deal where Cladakis was a promotions director—Anna has taken up a lot of roles in Daly’s life. Sometimes, she was a caddie, sometimes she would turn into a business partner. But for the most part, she’d be the “soul mate” John Daly had been looking for after four failed marriages (they got engaged in 2014). But wait till you hear what she’s done now. Like they say: It truly takes the cake! 

Earlier this week, Daly and his fiancée reached the Old Hickory Country Club in Tennessee for the John Daly Golf Invitational. The tournament was reportedly ideated by the golfer’s mother, Mama Lou, in 1991 to help raise funds for the Boys & Girls Club of the Arkansas River Valley—a non-profit organization that provides programs and services for youth aged 6-18. No wonder it was a special day for Daly which Anna made even more special, evident by the veteran’s own confession.

In a candid Instagram Story, the 1991 PGA Championship victor posted a photo of the two smiling together, tagging Cladakis with a message that read: “To my amazing fiancé, thank you for your unwavering hard work & generous heart that made our charity event this week such a HUGE success! Your dedication and compassion are truly inspiring!” The words hit differently, not just because they came from the famously unfiltered figure, but because they shined a beautiful light on the duo’s relationship that is rooted in more than just love—it’s a true partnership. Cladakis isn’t just along for the ride; she’s in the driver’s seat with him when it comes to their charitable work.

Notably, for the John Daly Charity Classic, with 24 team slots going for $10,000 a pop, the event was not just about golf. It included exclusive parties, food and drinks, goody bags, signed Daly memorabilia, and optional add-ons like mulligans and “Sure Putts” that added a fun, laid-back vibe to the competition. The event had a green twist: Ditching plastic and ramping up recycling efforts to keep the day as eco-friendly as it is entertaining, all in line with Daly’s growing commitment to sustainability. The day also included wellness activities, like yoga sessions and healthy-eating workshops, reflecting Anna’s commitment to community well-being. And this is just one the instances where the couple has heart-warmingly helped people in need. Over the years, the duo has championed causes across the country, consistently using Daly’s star power to uplift others.

Through it all—on and off the course—Daly continues to show that behind the loud pants and long drives is a guy with a big heart and a lot of gratitude, especially for the woman who’s been by his side through it all. And while the Nashville spotlight fades and Daly swaps charity polos for golf spikes, the show rolls on, which makes us curious…

Where will Daly play next?

John Daly isn’t just sticking around—he’s doubling down. Set to turn 59 later this week, the two-time major champ is proving age is just a number as he gears up for a jam-packed 2025 season on the PGA Tour Champions. While he’s technically retired from the PGA Tour, Daly shows no signs of slowing down. He’s got 19 tournaments on the books this year, more than the entire LIV Golf schedule, and he announced them in full Daly style with an Instagram reel: “Y’all better buckle up—2025 is gonna be a ride! … Let’s #GripItAndRipIt all over again!”

From Augusta National to Jacksonville, Dallas to Calgary, the fan-favorite is bringing his trademark energy to cities across North America. Other confirmed stops include Houston, Birmingham, Des Moines, Madison, Milwaukee, Akron, and St. Louis. Golf fans from coast to coast will have a shot at seeing Big John tee it up. He’s already made a few starts this season, including the Hoag Classic, Galleri Classic, and the James Hardie Pro-Football Hall of Fame Invitational, shaking off rust after undergoing emergency hand surgery in January.

Daly may be a showman, but make no mistake—he’s still grinding.