Kip Henley: PGA Tour Caddie & Tennessee Golf Champion
Kip Henley is a veteran PGA Tour caddie and accomplished golfer who won multiple Tennessee State Open championships before transitioning to caddying for top professional golfers like Brian Gay and Grayson Murray.
The Journey of Kip Henley: From Professional Golfer to Elite PGA Tour Caddie
Kip Henley has built a remarkable career in golf that spans over five decades. His journey from aspiring professional golfer to becoming one of the most respected caddies on the PGA Tour showcases his deep connection to the game and his ability to adapt when his original dreams took unexpected turns. While his initial aspirations of becoming a household name in professional golf didn’t materialize as planned, Henley found success through a different path that kept him intimately connected to the sport he loves.
Early Life and Golfing Beginnings
Born in Chattanooga, Tennessee, Kip Henley discovered his passion for golf as a teenager at Creeks Bend Golf Club. He quickly showed promise, winning the Chattanooga City Prep Championship and earning the Ewing Watkins Award for being the most outstanding junior golfer in the city. These early accomplishments fueled his belief that he was destined for a successful career as a professional golfer.
Henley continued his development at the University of Tennessee at Chattanooga, where he became an All-Southern Conference player. His collegiate success further reinforced his conviction that professional golf was his calling, setting the stage for his entry into the competitive world of professional golf.
Professional Playing Career
After college, Kip Henley’s professional playing career began with promise when he won the Tennessee State Open in 1982 as an amateur at Valleybrook. This victory prompted him to turn professional immediately, especially after witnessing competitors splitting significant prize money while he received a stainless-steel pickle tray as his amateur prize.
However, Henley’s path to PGA Tour stardom proved more challenging than anticipated. He struggled on mini-tours in Orlando before returning to Tennessee to work as a club professional. His career included positions at:
- Lake Tansi (two years)
- Heatherhurst Golf Club at Fairfield Glade (nearly two decades)
Despite not achieving his ultimate goal of PGA Tour success as a player, Henley built an impressive resume of regional accomplishments:
- Two Tennessee State Open championships
- Four Tennessee PGA Section Championships
- Five-time Tennessee PGA Section Player of the Year
- Three Tennessee State Scramble victories (including one paired with his brother Brent)
- Winner of The Golf Channel’s “Big Break II” in 2004
The “Big Break” victory at age 40 reignited Henley’s playing aspirations, leading him to quit his club professional job and make another attempt at tour golf. This opportunity provided him with six starts on the Nationwide Tour (now Korn Ferry Tour) and a spot in the PGA Tour event in Memphis, though he didn’t make any cuts.
Transition to Caddying
When his playing career didn’t reach the heights he had hoped for, Kip Henley found a new way to remain connected to elite professional golf through caddying. This career pivot proved to be a perfect fit, allowing him to apply his deep knowledge of the game while experiencing the highest levels of professional golf from inside the ropes.
Over his two-decade caddying career, Henley has worked with numerous accomplished players, including:
- Brian Gay (10 years, four victories)
- Vijay Singh (one win on PGA Tour Champions)
- Austin Cook (one PGA Tour win)
- Stewart Cink
- Boo Weekley
- Grayson Murray
- Heath Slocum
His partnership with Brian Gay was particularly successful, spanning a decade and resulting in four PGA Tour victories. Henley has described his caddying experience as providing invaluable insights into what it takes to compete at the highest level—knowledge he believes would have benefited his own playing career had he gained it earlier.
The Caddying Brotherhood: Kip and Brent Henley
One of the most unique aspects of Kip Henley’s story is that he shares his caddying journey with his brother Brent, who is three years younger. The Henley brothers both became fixtures on the PGA Tour as caddies, creating a rare family dynamic in professional golf.
Brent Henley’s caddying career included working for Woody Austin for ten years, during which they secured four wins plus a victory in the 2007 Presidents Cup. His entry into caddying came through Kip’s recommendation, leading to an immediate win with Garrett Willis at the 2001 Tucson Open—their first tournament together on the PGA Tour.
The brothers were occasionally paired together during tournaments, creating memorable moments. One particularly notable instance occurred in Memphis in 2007 when they made a friendly wager on which of their players would win. This family connection has provided both brothers with support through the ups and downs of their caddying careers.
Recent Career Developments
In recent years, Kip Henley has continued his caddying career while experiencing both triumphs and challenges. In 2023, he worked with Grayson Murray on the Korn Ferry Tour, helping him secure two victories that earned Murray a return to the PGA Tour. Despite this success, Murray surprisingly decided to “go another direction” in December 2023, leaving Henley looking for a new opportunity.
Following this unexpected change, Henley joined Heath Slocum’s bag on the PGA Tour Champions when Slocum turned 50 in 2024. This transition to the Champions Tour represents a new chapter in Henley’s caddying career.
In a personal achievement, Henley won the Tennessee Senior State Open Championship in June 2023, shooting rounds of 70-71 for a 3-under-par total. The victory was particularly meaningful as he dedicated it to his mentor, the late Warren Huddleston, a respected figure in Tennessee golf. Henley secured the win with a dramatic 15-foot birdie putt on the final hole.
Life as a PGA Tour Caddie
Kip Henley has been open about both the rewards and challenges of life as a professional caddie. He describes the profession as “a unique gig” where job security can be tenuous—”You can just get flicked away like a bug”—but the opportunities are extraordinary, including traveling the world and experiencing the most beautiful golf courses in ideal conditions.
Throughout his caddying career, Henley has walked the hallowed grounds of the world’s greatest golf courses and participated in all four major championships. He considers Augusta National Golf Club and the Masters Tournament to be the pinnacle experience, describing it as incomparable even to other iconic venues like St. Andrews and Pebble Beach.
The physical demands of carrying a 40-pound golf bag for more than 10 miles per day haven’t diminished Henley’s enthusiasm for the job. At 64 years old (as of 2024), he continues to embrace the challenges and rewards of caddying, driven by his passion for the game and the ongoing connection it provides to competitive golf at the highest level.
Reflections on a Golf Life
Looking back on his career, Kip Henley has gained perspective on the mental aspects that influenced his playing days. He reflects that while many consider his brain to be his strength, he believes it may have been his weakness as a player: “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.”
This insight has informed his approach to caddying, where he’s been able to observe how elite players handle themselves mentally. Henley believes that if he could have learned what he discovered during his first year caddying for Brian Gay before his playing career, he “would have gotten those five green jackets,” suggesting he wasn’t as far from competing successfully as he once thought.
Despite not achieving his original dreams as a player, Henley has found fulfillment through caddying and maintained his competitive edge. He continues to compete in amateur events, having regained his amateur status. In April 2024, he teamed with his brother Brent to win the North Georgia Four-Ball in Dalton, demonstrating that his playing skills remain sharp.
The Evolution of Professional Caddying
Kip Henley has witnessed significant changes in the caddying profession throughout his career. What was once viewed as a job for “modern-day vagabonds” hanging around Monday qualifiers has transformed into a respected and well-compensated profession.
The Changing Landscape of Tour Caddying
According to Brent Henley, “It’s gotten to be such big money that they kind of weeded those old guys out. 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.”
This evolution reflects the increasing professionalization of all aspects of golf, including the support roles that surround elite players. Today’s caddies are often highly educated, technically savvy individuals who provide comprehensive support to their players, from detailed yardage calculations to mental coaching and strategic planning.
The Caddie-Player Relationship
The relationship between caddie and player is complex and often intense. Kip Henley has experienced both long-term partnerships, like his decade with Brian Gay, and brief stints that ended unexpectedly, as with Grayson Murray.
After being let go by Murray in December 2023 following a successful season with two wins, Henley demonstrated remarkable professionalism, stating: “I’m disappointed and sad it worked out this way but believe it or not I’m not really mad at Grayson. He’s not a bad person. It’s just a tough relationship out there at times.”
This perspective highlights the business nature of modern caddying, where results don’t always guarantee job security, and personalities and preferences play significant roles in these professional partnerships.
Favorite Courses and Memorable Experiences
Throughout his extensive career as both a player and caddie, Kip Henley has experienced many of the world’s finest golf courses. His travels have given him unique insights into these venues from both playing and caddying perspectives.
Preferred Venues
When asked about his favorite places to caddie, Henley mentioned Harbour Town Golf Links as his all-time favorite spot. This Pete Dye, Jack Nicklaus, and Davis Love III design, established in 1967, hosts the RBC Heritage Classic and clearly holds special significance for Henley.
He also noted that while Maui offers an incredible total experience, the physical demands of walking the course there are particularly challenging: “Maui will kill ya walking but the total experience is cool as can be.”
The Augusta Experience
Both Kip and Brent Henley consider their multiple appearances at Augusta National Golf Club for the Masters as their favorite tournament experiences, despite the physical and mental demands of the week.
Kip expresses particular reverence for Augusta: “I caddied at St. Andrews. I’ve been to Pebble Beach. But let me tell you, nothing touches Augusta.” This sentiment reflects the special place the Masters Tournament holds in golf, especially for someone who grew up in Chattanooga reading the local newspaper’s extensive Masters coverage.
The Henley Brothers’ Legacy in Golf
Together, Kip and Brent Henley have created a unique family legacy in professional golf. While they didn’t achieve their childhood dreams of becoming famous players, they found a different path to making their mark on the game.
A Shared Journey
The brothers’ parallel journeys through professional golf—first as aspiring players, then as club professionals, and finally as tour caddies—have given them a rare shared experience. As Kip notes, “There has been plenty of laughter along the way,” and they’ve been able to support each other through the highs and lows of their careers.
Their story illustrates how passion for a sport can find expression in unexpected ways. Though neither brother became the tour star they once envisioned, both have experienced the thrill of victory at the highest levels through their caddying careers and maintained their competitive spirits through continued participation in amateur and senior events.
Continuing Competitive Spirit
Even as they’ve aged, the Henley brothers have maintained their competitive edge. In April 2024, they teamed to win the North Georgia Four-Ball in Dalton, and Brent defended his title as senior champion at the Men’s Metro tournament at Lookout Mountain Club.
Kip’s victory at the 2023 Tennessee Senior State Open demonstrated that his playing skills remain formidable, and his dramatic winning putt showed that his competitive fire still burns brightly.
Beyond Professional Golf: Kip Henley’s Other Interests
While golf has been the central focus of Kip Henley’s professional life, he has also developed other interests and connections within the golf world that extend beyond his playing and caddying careers.
Connection with Club Pro Guy
Henley has formed a friendship with the popular golf content creator known as “Club Pro Guy” (CPG), a satirical character who has built a significant following on social media. When CPG shared a video in September 2024 announcing his retirement as a head golf professional, Henley commented on the post, indicating their personal connection.
When asked if CPG was truly retired or if it was just another gimmick, Henley replied: “I would never out him. CPG will always be the ultimate in golf content creator. He’s a sharp solid husband, father and a pillar in his community. He’s actually too smart to play this dumb for this long. I wish yall could know him like I know him!”
This interaction reveals Henley’s appreciation for the humorous side of golf culture and his connections beyond the professional tour world.
Samantha Yates is a creative writer and journalist with expertise in content creation and editing. She holds an MA in Creative Writing and brings professional experience from Lionbridge, where she developed engaging content for leading technology companies
