BELLEAIR, FLORIDA – NOVEMBER 15: Jennifer Kupcho of the United States plays a shot from the 18th tee during the third round of The ANNIKA driven by Gainbridge at Pelican 2025 at Pelican Golf Club on November 15, 2025 in Belleair, Florida. (Photo by Julio Aguilar/Getty Images)
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Daring swings certainly have paid off in a large way for Jennifer Kupcho. The four-time LPGA Tour winner arrived at this past weekend’s Annika driven by Gainbridge at Pelican sitting 4th in the AON Risk Reward Challenge—the top circuit’s season-long tournament-within-a-tournament that hinges on how players fare on a designated hole each event and culminates with a million-dollar prize.
Kupcho came up big on the brawny par-5 14th, chosen because fairway bunkers in the landing zone put a premium on accuracy off the tee, and a trap guarding the front of the green also factors into whether to lay up or take a run at the dance floor in two.
The clutch performing Wake Forest product, who has been in the spotlight since topping the leaderboard at the inaugural Augusta National Women’s Amateur six years ago and later starred on three Solheim Cup squads, birdied the hole in the first round and then eagled it in the second to clinch the Challenge’s seven-figure payout. Jen’s prowess wasn’t confined to the professional services giant’s curated pressure cooker—she finished the tournament as the runner-up, adding an additional $303,188 to her coffers.
Vibes Matter
Kupcho gave a lot of kudos to her playing partner Auston Kim, whose rocksteady tempo and mellow demeanor helped her stay in a positive frame of mind between swings.
“Watching her—with a tempo so good, it’s the same for literally every swing…that really helped to kind of settle me down and really just relax,” Kupcho explained. She contrasted those game-enhancing vibes with being paired with players who might get sped up when they get frustrated, emphasizing the mental rigor required to stay in your own bubble on the course in those situations. Whereas with Auston, “it was really easy to just talk with her and just stay ready-to-go and it felt like having fun the whole day.”
Considering the intense game face Kupcho typically sports, it is interesting that she credits Kim’s easygoing nature with helping her play her best. Even when Kupcho plays for fun with no television cameras in tow, that competitive fire still burns hot. Her in-the-zone game face was even on full display when she was dating her now-husband.
She recounted a story her husband likes to tell about the first time she played golf with him and his parents. He forewarned them coming into the round that she was fiercely competitive and wouldn’t so much as speak a word if she wasn’t winning.
“I was in fact losing through fifteen holes and so I didn’t talk to them. I did come back and won,” she added. “Afterward, they were like, ‘Wow, you weren’t kidding—she’s very competitive.’ Obviously, we’re still married, and they love me, so it was great.”
GALLOWAY, NEW JERSEY – JUNE 08: Jennifer Kupcho of the United States celebrates on the 18th green with David Taylor after winning the ShopRite LPGA Classic presented by Acer 2025 at Seaview Bay Course on June 08, 2025 in Galloway, New Jersey. (Photo by Isaiah Vazquez/Getty Images)
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Go Big or Go Smart
Overall, on challenge holes this season Kupcho favored a gutsy approach, going for 68% of greens (fifth on tour) and making her attempts 33% of the time (second on tour).
Asked if her tendency toward bolder plays on challenge holes, as the stats imply, had been a conscious strategy all season, Kupcho downplayed that notion. She noted the “go big or go home” mentality only really came into play at the Annika when all the chips were on the line. Earlier in the season her focus was dialed in on making smart decisions and maximizing scoring opportunities. The million-dollar prize, she added, wasn’t a driving factor, “the holes they pick are specifically risk/reward holes,” Kupcho explained. “You can go for it and be rewarded, or you could go for it and not be rewarded,” she said stoically.
The tourney that resulted in the biggest payday of her career wasn’t all about tactical decision making and pulling off the hero shot when it was called for. Kupcho also found some time to let loose and snap a selfie with a hero of hers, WNBA superstar Caitlin Clark who played in the event’s Pro-Am with teammates Sophie Cunningham and Lexie Hull serving as her caddies.
“I’m a very big fan of those three,” she said. “I missed watching only two of their games this year. I’m a very devoted Fever fan.”
That blend of composure and enthusiasm has defined her competitive mindset on the course all season. Last year Kupcho admits to having “struggled a little bit mentally.”
“This year, I’ve been able to just take every shot and take every tournament how it’s going to be, being more accepting of the results…instead of deciding what is going to happen before it actually does. I think that is something that has really helped me succeed this year,” she added.
Meanwhile, challenge sponsor Aon is still elated in the afterglow of Kupcho’s bravura eleventh-hour surge—leapfrogging three players to take the big prize and in the process delivering a decidedly Hollywood ending to the seventh edition of the contest.
“We’ve had some pretty exciting ones the last several years but I can’t remember one that really came down to the absolute wire like this one did. It felt like anybody’s challenge coming into the week and it was thrilling for it to end the way it did,” Taylor Strick, AON’s head of partnerships, said.
“She did exactly what she needed to do when she needed to do it. I couldn’t be more proud of the challenge as it played out and of Jennifer for finishing so strong, coming from behind and taking it home,” she added.
When the Aon prize debuted, its seven-figure purse was the largest single-event payout available to women in professional golf. The landscape has shifted quickly: today, winners at marquee events like the U.S. Women’s Open ($2.4 million) and the KPMG Women’s PGA Championship ($1.8 million) have eclipsed that mark. Even so, the Challenge remains one of the LPGA’s most impactful season-long financial bonuses, especially given how tightly prize money is distributed across the tour. Kupcho hasn’t made any grand plans for her winnings yet, focusing instead on prepping for the CME Group Tour Championship and hoping her game’s uptrend has further legs.
“I definitely feel like my game is trending in the right direction. I’ve been hitting the ball really well and putting really well so I’m just excited to see how my game shows up this week.”