Brian Gay was without a sports agent until a fiery, ambitious one stepped in: his wife, Kimberly

Brian and Kimberly Gay

The Gays in Hawaii for this year’s Sony Open, where Brian finished 72nd. Guaranteed he’ll get a talking-to from his agent.

P.S. Yushin/

Unless you were an obsessive golf fan, the arrival of Brian and Kimberly Gay onto the PGA Tour at the turn of the century was easy to miss. Yes, he’d been everybody’s All-American at Florida and she was, to borrow Brian’s favorite phrase, “a tornado with lipstick.” But for most of the 2000s, Brian struggled to find his place on Tour, just barely getting by with a magical short game. He was one of the anonymous journeymen that the camera rarely finds. Meanwhile, Kimberly threw herself into raising two daughters and, at times, a Tour pro.

“Brian is a very quiet, laid-back, introverted guy who’s happy to be on the couch watching football,” says Gay’s longtime swing coach, Joe Mayo. “Kimberly has a take-charge kind of attitude and so she’s been great for him, pushing and motivating him and dotting all the i’s in their life.”

In 2008, Brian finally broke through for his first win, at Mayakoba, and the following season he turned into a semi-star by winning twice, including a stunning 10-shot romp at Hilton Head.

The Gay family poses with the Heritage Classic trophy in 2009. getty images

It was a remarkable emergence for one of the shortest hitters on Tour. Brian had an agent, but Kimberly became increasingly involved as her hubby began fielding more requests for interviews, charity appearances and corporate outings. By late 2012 Brian was without representation altogether. At that year’s tournament in Disney, Kimberly was walking in the gallery — “I try to never, ever miss a hole” — when she spotted a familiar face from various golf gatherings: Mike Flaskey, a top executive at Diamond Resorts. She said the first thing that came to mind: “Mike, when are we going to sit down and do a deal?”

Flaskey was amenable, and by Tuesday of the following week Kimberly had emailed him a 13-page proposal, which led to the creation of an “ambassador” program starring Brian.

(Upon signing, the Gays didn’t have to part with the 20 percent that agents traditionally skim off the top of endorsement deals.) There wasn’t time to get logoed hats made for Brian’s first start under the deal in Hawaii, so Kimberly bought blank caps at the mall and drove around Honolulu to find an embroiderer.

It’s great to keep the money in the family when Brian signs a deal, but the reason I do this is to be a role model for our daughters.

The following week Brian won the Bob Hope and collected a $25,000 victory bonus that would not have been paid if he hadn’t been wearing the Diamond Resorts hat. “She can pull a rabbit out of a hat like nobody else,” says Brian with a chuckle.

Kimberly has served as Brian’s agent ever since, corralling deals with Sligo, G/Fore, EasyGo, PapaNicholas Coffee and Sentinel Spine, as well as the ongoing relationship with Diamond Resorts. Chris Stroud, winner of the 2017 Barracuda Championship, was so impressed by her work that in 2018 he asked Kimberly to represent him too. That forced her to formalize the business and thus GSD Sports Management was born. (It stands for Get, uh, Stuff Done.)

At the 2019 Players she was invited, for the first time, to the annual meeting between agents and Tour brass. Of the 80 or so aspiring Jerry Maguires in the room, Kimberly was one of only two women. “I’ll be honest, that was an emotional day for me,” Kimberly says. “Yes, it’s great to keep the money in the family when Brian signs a deal, but the real reason I do this is to be a role model for our daughters. For them to be proud of me is the most important thing.”

Brian Gay
Brian Gay rallies to win Bermuda Championship in playoff
By: James Colgan

Mission accomplished. Inspired by her mom, Makinley Gay is majoring in sports management at Florida and simultaneously pursuing a master’s in international business. The hope is that, among other things, she’ll bring a younger, fresher perspective to GSD’s digital-media offerings. Kimberly’s ambitious goal is to someday have 20 players in her stable. She’s already diversifying, having signed Maurice Allen, the 2018 Long Drive champion, and venturing into event management around their hometown of Windermere, Fla. Kimberly’s is not the only reinvention in the Gay household.

Injuries and the vagaries of aging had kept Brian winless since the ’13 Hope. Finally, at Colonial in 2019, he gave in to Mayo’s beseeching to chase more distance. Mayo, who earned a modicum of fame for his sardonic Twitter nom de plume Trackman Maestro, says that back then Gay generated 107 miles per hour of clubhead speed and 154 mph of ball speed with his driver, carrying his tee shots barely 260 yards. After learning to lift his left heel on the backswing and lengthen his turn, Gay’s speed quickly spiked to 117/173 and he began flying it up to 40 yards farther. The hard work began to pay off that fall in Bermuda, when Gay tied for third. (“I actually didn’t even want to go play there because that weekend was the Florida-Georgia game, but Kimberly talked me into it.”) But Brian struggled throughout the 2020 season.

“I might have been pressing a little bit,” he says. He was aware that, for the first time, colleagues were watching him on the range and whispering about how far he was hitting the ball.

Brian, Kimberly and their daughters celebrate Brian’s Bermuda Championship win. Courtesy of Kimberly Gay

He finally found some peace of mind returning to Bermuda in November, and a month shy of his 49th birthday Brian birdied the 72nd hole for an out-of-nowhere victory, capping what Mayo calls “one of the most remarkable careers in golf history. I mean, for 20 f—ing years he was the shortest hitter on Tour. If Brian can keep adding speed, Dustin Johnson and everybody else can pack up and go home, because nobody else has this guy’s heart or toughness or ability to get the ball in the hole.”

Kimberly memorialized the victory with an emotional video capturing the ups and downs of their two decades on Tour. “I’m just so, so proud of him,” she says. That’s a wife talking. And what does the victory mean to Brian Gay’s agent? “Let’s just say there are some exciting opportunities we’re pursuing,” says Kimberly, “but I’m not at liberty to discuss them yet.”

generic profile image

Alan Shipnuck

GOLF senior writer Alan Shipnuck writes longform features and a monthly column for GOLF Magazine and has his own vertical on entitled “The Knockdown,” which is home to podcasts, video vignettes, event coverage and his popular weekly mailbag AskAlan. He is the author of five books on golf, including na­tional best-sellers Bud, Sweat & Tees and The Swinger (with Michael Bamberger). Shipnuck is very active on Twitter, with a following of 50,000.