The world of professional golf is filled with unsung heroes who quietly shape the careers of the sport’s biggest stars. While the spotlight typically falls on players who claim victory after victory, there’s a whole cadre of caddies whose strategic insights and emotional support prove just as crucial to success on tour. Among these skilled loopers is Brennan Little, the veteran caddie who has guided Gary Woodland through some of the most significant moments of his career.
The relationship between professional golfers and their caddies has evolved dramatically over recent years, with loopers becoming far more than just bag carriers. The PGA Tour’s recent Instagram post captured this perfectly, showing Garry Woodland making an extraordinary promise to his caddie, Brennan Little. “If you qualify for the Senior PGA Championship, I’ll carry your bag,” Woodland declared in the video, generating thousands of reactions from golf fans. This casual bet, now turned serious commitment, offers a rare glimpse into the dynamics of one of golf’s most successful player-caddie duos, whose partnership extends well beyond typical professional boundaries into a friendship built on mutual respect and shared triumphs.
Who is Brennan “Butchy” Little? Meet the veteran caddie behind Garry Woodland’s success
Brennan Little, affectionately nicknamed “Butchy” by Woodland, has been by Woodland’s side since 2016, forming a partnership that has weathered major championships, health challenges, and personal triumphs. The Dallas, Texas resident brings an impressive resume to the role, having previously guided Mike Weir to victory at the 2003 Masters—the first major championship win by a Canadian golfer. Before joining forces with Woodland, Little also helped Camilo Villegas capture the 2014 Wyndham Championship.
But their signature triumph came at the 2019 U.S. Open at Pebble Beach, where Little’s steady guidance helped Woodland claim his first major championship by three strokes over Brooks Koepka. “It’s right up there with winning the Masters,” Little said about the victory, highlighting its significance in his 26-year caddying career.
Pebble Beach remains a nostalgic venue for Woodland. During a TGR service, he shared the winning advice he received from Butchy that proved decisive. Leading the championship by one stroke on the fourteenth hole, Woodland faced a critical decision. “I was playing with Justin Rose, who I know well and Justin just lays up on the par five,” Woodland recalled. Standing 265 yards out in cold conditions, he told Butchy he wanted to lay up—the first time he’d ever suggested that in competition.
Butchy, however, challenged him, catching Woodland off guard. “I’ve watched the shots all morning. Nobody can get that wide shot close. It’s too tough. Hit this over the green and we’ll get it up and down,” the caddie insisted. The advice led to what Woodland calls “the best swing of his entire career,” a moment he credits entirely to his caddie’s conviction and insight.
Their first win together came at the 2018 Waste Management Phoenix Open, establishing a partnership that has since become one of golf’s most enduring duos.
Woodland has frequently credited Little’s influence during pressure situations. “Brennan’s work ethic helps in every tough situation…provides confidence,” the PGA Tour star has said, particularly noting his caddie’s calming presence during the final round of their U.S. Open victory. This support became even more crucial during Woodland’s 2023 health struggles when he underwent brain surgery and faced a difficult recovery process.
Their professional synergy extends beyond the ropes, revealing a relationship built on trust, mutual respect, and shared experiences that transcend typical player-caddie dynamics.
Beyond the course: Little’s lifestyle and unique bond with Woodland
Beyond calculating yardages or reading greens, Brennan Little balances professional dedication with personal passions. The Dallas-based caddie carries fishing gear on tour for weekly angling sessions between rounds. His competitive spirit extends to following the Dallas Stars, Washington Commanders, and Toronto Blue Jays passionately. Little approaches caddying methodically, using multi-colored Sharpies for detailed green mapping. “You can never have enough colors for mapping greens,” he explains about his favorite tool. When off-tour, Little volunteers with the Boys & Girls Club in Plano/Frisco, demonstrating a community commitment equal to his professional dedication.
Mutual respect defines the Woodland-Little partnership, transcending their professional relationship. This became evident when a casual joke evolved into a serious commitment after Little qualified for the 2025 Senior PGA Championship. “Gary said if I qualified, he’d carry the bag. It started as a joke, but we shook on it,” Little revealed recently. Woodland confirmed, “I owe him one after all these years. We’ll make it work schedule-wise.” This extraordinary promise might force Woodland to skip the Charles Schwab Challenge, which overlaps with the Senior PGA Championship at Congressional Country Club this May. Such a sacrifice demonstrates their deep connection and will place Woodland in the unusual position of providing advice rather than executing shots.
Their relationship proved particularly crucial during challenges. When Woodland underwent brain surgery in 2023, Little provided emotional stability alongside professional support. Their partnership during the 2024 comeback season—making 15 cuts in 26 starts, including a Top-10 finish—revealed a genuine friendship built on shared triumphant and trying experiences.
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