Paul Payne: Brent and Kip Henley Have Experienced Memorable Journey In Golf (2024)

Separated in age by three years, Kip and Brent Henley both knew early in life that their career paths would revolve around the game of golf. Their now-distant dreams once envisioned donning multiple green jackets, hoisting iconic trophies aloft and becoming household names within the sport.

But their journey – full of detours, disappointments and periods of success - took a different twist, straying from their original script. Their odyssey has no doubt been memorable, and there has been plenty of laughter along the way.

Golf has been – and continues to be – the axis around which their professional and personal lives revolve. The path to personal stardom remained elusive, just beyond their grasp, all the while having a front-row seat to greatness. But it has been one that they experienced together, sharing both the exhilaration and heartbreak along the way.

There really wasn’t a backup plan in place since picking up golf as teenagers at Creeks Bend Golf Club. They firmly believed they were both destined to enjoy fulfilling lives as professional golfers.

While the brothers did indeed achieve their goals of obtaining PGA Professional status, their playing careers fell short of their initial expectations. Instead, their alternate path to the PGA Tour was hard-earned as long-tenured caddies.

The Henley boys have seen it all, having walked the hallowed grounds of the world’s greatest golf courses and all four majors. They have taken part in Presidents Cup celebrations, rubbed shoulders with this generation’s greatest golfers and have amassed a treasure trove of memories that would take another lifetime to recount.

Unfortunately, there have been times of disappointment as well. Whether it came through near misses while playing competitively or being fired as a caddie, their itinerary has been anything but smooth.

But through it all, they still had each other. As two of five siblings who still remain closely connected, Kip and Brent always knew they had a sympathetic ear to vent their frustrations and a trusted brother with whom to celebrate successes.

They both experienced the thrill of victory on the PGA Tour. In fact, Brent had a win carrying for Garrett Willis in their first tournament on the Tour at Tucson in 2001 thanks to Kip referring his brother for the job. He then accompanied Woody Austin to four wins plus a victory in the 2007 Presidents Cup matches over the course of ten years together. He had short flings carrying for other golfers over his 20-year career, but none of those others found the winner’s circle.

Kip was also on the bag for numerous wins, most notably four victories with Brian Gay during their decade together. Additionally, he was part of Austin Cook’s lone PGA Tour win and won once with Vijay Singh on the PGA Tour Champions during a memorable five-week stint.

Kip is currently working for Champions tour rookie Heath Slocum, a job he picked up earlier this year when Slocum turned 50. This followed an unforeseen return to the unemployment line when Grayson Murray fired Kip last December. Murray had regained full Tour status last season with the veteran looper by his side. Tragically, five months later, Murray committed suicide in May having publicly admitting he battled mental illness and substance abuse for several years.

It was another bitter dose of reality for Kip of how fragile his chosen career path can be at times.

“Our gig is a unique gig, man,” Kip said. “You can just get flicked away like a bug. But we also get to travel the world, caddying in China, Korea and Mexico. Walking along Pebble Beach when it's 75 degrees outside and the waves are crashing. I just love caddying with all my heart. I love it.”

Call it an obsession, or possibly a destined career path once the options for competing professionally dried up. No matter the reason, the Henley boys have made an impact within professional golf that few other families can proclaim.

The original plan for Kip was to play professionally. After competing at the University of Tennessee at Chattanooga following his prep career at Central High School, he won his first of two Tennessee State Opens in 1982 – this one as an amateur at Valleybrook – to jumpstart his pursuit of becoming a Tour player.

“I beat Bob Walcott in a playoff, who was Tennessee's golden child,” Henley said. “Mike Nelms and Gary Robinson finished T3, and they split $6,000. I was expecting a bunch of gifts and I ended up with a stainless-steel pickle tray. When I saw them get all that money, I turned pro immediately. Q-school was coming to Valleybrook so I knew the stars were lining up and I’d buzz through that and be on the Tour in about a year.”

After turning pro, Kip had a reality check, struggling on the mini-tours in Orlando before returning to Tennessee to become a club professional. He worked two years at Lake Tansi before spending the next two decades at Heatherhurst Golf Club at Fairfield Glade. But the itch to chase the elusive dream of making it to the PGA Tour once again reared its head, fueled by him winning The Golf Channel’s “Big Break II” in 2004.

“I was only 40, so I quit my job and tried again and failed again,” Kip said. “My wife (Sissi) talked me into trying out for the Big Break, and my door opened back up again. I had six starts on the Nationwide Tour and played the PGA Tour event in Memphis that year, but didn’t make any cuts.

“Looking back, my brain was my weakness. All my friends think my brain is my strength, but I never really felt like I belonged. I always felt like it was some unattainable goal that maybe I wanted so bad it created seeds of doubt. But now being 63, I've learned how to win golf tournaments.”

While not reaching his ultimate goal, Kip has accumulated quite the résumé on the state level. In addition to his two State Open titles, he won four Section PGA Professional championships, was five-time PGA Section player of the year and won the State Scramble three times, the last coming in 2005 paired with Brent. Proving he still has plenty of game, he captured the Senior State Open with a final-hole birdie last summer.

Brent’s journey was different after playing collegiately at Middle Tennessee State University. While a talented golfer in his own right, he lacked the self-confidence of his brother and became a club professional at Harbor Town Golf Links on Hilton Head Island. He ventured thru Q-school and mini-tours after snagging a big paycheck from the win by Willis, but decided to pursue the path of a caddie after his giving up on becoming a tour pro.

“I had enough talent to win without working hard in high school. But in college I knew I had to play better than I did in high school,” Brent said. “Then when I turned pro, I wasn’t sure my best was even good enough to win. Once I started caddying, I realized my game wasn’t as far off as I thought. So much of winning comes from confidence, and I didn’t have it at the time.”

Brent teamed with Austin in 2002, and they became a dynamic duo for the next decade. Austin had lost his Tour card and was relegated to Q-school to regain his status. It was there that Brent gained a new appreciation for the fine line between success and failure on the PGA Tour.

“I kept thinking, ‘Man, I don't get it. I watched him hit, and it was amazing how good he was. How is he not winning?’ He then birdied 16,17 and 18 on the final day of Q-school to get his card back. I'll never forget I sat down on the curb before he even signed his card and cried like a baby. It was the coolest thing I'd ever seen, a guy stack it up when he needed it the most. It was his life on the line, and mine was, too, because I wasn’t going to get another caddie gig.”

The most infamous incident during Brent’s time with Austin occurred in the Presidents Cup at Royal Montreal Golf Club, the site of this year’s event. Brent encouraged Austin to attempt a shot with his ball submerged under water, which resulted in the golfer losing his balance on his swing and tumbling face-first into the pond.

“It was my fault,” Brent said. “But that's because we grew up at Creeks Bend and I was used to playing balls in water when it flooded. I had figured out you could hit a golf ball out of water. But Woody went in there and tried to hit it like a bunker shot, and his club just skipped off. He came out of the water cussing me.”

Meanwhile, Kip had secured Brian Gay’s bag, and that relationship was flourishing as well as the Henley brothers became regular fixtures caddying on the Tour. They wound up being paired together five times during this stretch, the most memorable of those occurring in Memphis in 2007.

Adam Scott held a one-stroke lead over David Toms, and Austin and Gay were in the next to last group trailing by four and five shots, respectively, entering Sunday’s final round. The night before, the brothers decided on a friendly family wager.

“We made a pact in our house that if either of us won, we’d have to pay to other one $10,000 from our winnings,” Kip said. “We reduced it to $5,000 because we figured nobody's beating Adam Scott because we played with him on Saturday and he didn’t miss a shot.”

The following morning, Kip totaled his car right outside the golf course gate to put him behind schedule. But when he finally arrived, he noticed how crisply Austin was striking the ball on the driving range, thus deciding to up the ante.

“It was the only time I was late in 20 years of caddying,” Kip said. “I'm watching Woody hitting seeds just dead straight, so walking up the cart path to one tee I told Brent, ‘Let's push it back to $7,000. Your guy’s striping it and you’ve already won a ton of money,’ so we agreed on $7,000.”

Austin put together a stellar back nine to make a charge when it dawned on the brothers the roars for the final group had become curiously silent.

“We’re on 16 tee and I said to Brent, ‘I haven't heard a peep behind us in a bunch of holes. Y'all might be in this’ as there were no scoreboards back in the day,” Kip said.

Austin wound up shooting a 62 to win by five shots, with Gay placing fourth. The outcome culminated in a brotherly celebration on the 18^th green.

“I lifted Brent boy up from behind on the green after Woody had putted,” Kip said. “I was so happy for him, but he had to write me a $7,000 check in the parking lot. That was a special moment.”

Despite their successful partnerships, at some point golfers need to hear a different voice and opt to make a change in caddies. Both brothers understand this is one of the pitfalls of their profession.

“It’s a lot about chemistry, and over time things can become stale,” Brent said. “You spend more time with him than his family and so you’ve got to have something to talk about. It can’t just be about golf. You’ve got to have something in common away from the game.”

The isolation from family while on the road creates a deep bond between golfers and their caddie, fostering a sense of safety and comfort for both parties.

“You become a team,” Kip said. “That’s why Brent went and cried on the curb when Woody got his card back. You're so involved with your guy. And if he brings you in, you know, and you're on that team, it does so much for him and you. You get an up-close view to something you always dreamed about and you feel like you’re a part of their success.”

Which is why Murray’s decision to part ways with Kip last December was particularly painful.

“I thought I was on his team, and then he fired me right out of left field,” Kip said. “That was the nastiest thing to happen in my years of caddying. I believed in him. It just shows the fragility of what we do. When he won the next event at Sony with me sitting on the couch, it was painful to watch.”

Kip had been a part of Murray’s march in regaining his Tour card during their time together, winning twice on the Korn Ferry Tour and posting a pair of Top 10s on the PGA Tour. Finally, after years of struggling, Kip believed he was back on top with another rising star.

“We're starting a brand-new season with full status, and I know he's gonna win in no time,” Kip said. “It was hard not to be somewhat bitter, thinking that I had helped him rebuild his career. Let’s be honest - Grayson won because he can hit a five-iron 225-yards dead straight every single time. But part of me felt like I helped him screw the wheels back on, to deal with his demons while reaching his golf potential. I had been telling him we were going to win and be in the next Masters.”

Securing a new gig with Slocum has been cathartic for Kip in moving past his disappointment. But hearing the news of Murray’s death while working a Champions Tour event in Michigan came as a shock, filling him with sorrow and compassion.

“We were riding to scoring after our round and one of the caddies on the driving range screamed, ‘Kip, did you hear that Grayson’s dead?’ It hit me like a ton of bricks. I was riding with Greg Chalmers, and he put his hand on my shoulder to comfort me. It was just devastating. A million emotions went through me in two seconds.”

The Henleys have witnessed a dynamic shift within their profession since they first began looping. No longer are caddies viewed as modern-day vagabonds, hanging out at Monday qualifiers hoping to pick up a bag in order to cover their rent.

“It's gotten to be such big money that they kind of weeded those old guys out,” Brent said. “It’s definitely changed. It truly wasn’t a job for the 20 years I did it. But when it became a job, I decided to walk away.”

Brent’s exodus from the profession was chronicled on the ‘X’ social media site two years ago when he stated “I got hired and fired in less than 24 hours!! Never caddied 1 hole for the guy. That is a first. In Kip’s words ‘caddying ain’t easy’.”

The younger Henley had finally decided he’d had enough, although he wouldn’t mind snagging a bag for 8 to 10 events each year. But his phone hasn’t rung.

As for Kip, the stress and physical demands of the job toting a 40-pound golf bag more than 10 miles per day still gets him out of bed every morning. It provides an ongoing connection to a game he has loved for more than 50 years, enabling him to better understand his own mission within the sport.

“I've always said that when I turned pro in ’82, if God could have made me caddie on the PGA Tour for one year first, I would have gotten those five green jackets,” Kip said. “If I could have learned what I learned in that first year of being with Brian Gay and watching how a real champion handles himself, I wasn’t as far away as I thought I was in being able to compete out there.”

Both Henleys list their multiple appearances at Augusta National Golf Club for the Masters as their favorite tournament, even though the week is physically and mentally draining.

“I caddied at St. Andrews. I’ve been to Pebble Beach. But let me tell you, nothing touches Augusta,” Kip said. “If you're a Chattanooga kid who grew up in the era of Sam Woolwine writing for the Free Press about the Masters with that two-page color spread on Sunday, I couldn’t wait to get my hands on that paper. Then getting to be a part of it, playing the golf course and going through the gate? You just can’t describe it.”

With Kip still active on the Champions Tour with Slocum, the brothers still find time to compete. They teamed to win the North Georgia Four-Ball in Dalton back in April, and Brent will be defending his title as senior champion of the Men’s Metro this week at Lookout Mountain Club.

Both have aspirations to qualify at Lookout Mountain next week for the U.S. Senior Amateur to be held at The Honors Course in August, but Kip’s duties on the Champions tour have left him precious little time to hone his game.

They laughingly dream of advancing to a final match showdown with the U.S. Senior Amateur title hanging in the balance. Unsure of how to handle the predicament, they would prefer the USGA deem them co-champions as neither would feel right denying his brother of the prestigious prize.

They hope to find a platform to chronicle their countless stories over the years, and Kip has an active presence on social media where he is known as “The People’s Caddie”, expressing his unfiltered views on an assortment of topics to his large base of followers.

Ultimately, they would like to find a way to bring their unique homespun delivery and knowledge from inside the ropes into golf’s version of the “Peyton and Eli”, commentary on the PGA Tour akin to what the Manning brothers have done for NFL broadcasts.

“Six years ago, I said to Brent we needed to get a camera and call the golf,” Kip said. “Get a YouTube channel with the camera on us while we watch the golf telecast. Tell the people turn the golf on, turn the sound off and let us describe all the action. I promise you - we’d have five million viewers in two weeks.”

Given their resilience and perseverance, I wouldn’t put it past the Henley brothers. They have somehow managed to reconfigure their childhood dreams into a new paradigm, while still remaining connected to the game they love. Maybe it’s simply the next step on their quest.

“In everything I've ever done in my life, I had a clear path,” Kip said. “When I walked away from a 40-hour work week club pro job where I could play in every section event because I wanted to still be a tour player at age 40, I had a clear path.

“And then when I started caddying, I was so broke and didn't have a club pro job, so I had a clear direction then. I was going to go caddy because I had no other option. It was a clear path. I just don’t want to give up what I love, and I’m just looking for that next path.”

Regardless of the outcome, the Henley brothers have made an impact on the game they embraced as teenagers. Their competitive juices have not dried up, and they still have plenty left in the tank to win trophies. But the best part of it all is that they have had each other riding shotgun on their incredible journey.

* * *

Paul Payne can be emailed at paulpayne6249@gmail.com