After gaining his PGA Tour card in 2023, Harry Hall has enjoyed multiple successes since, with the stand-out moment coming at the ISCO Championship in 2024.
Midway through 2025, Hall switched caddies, calling on experienced practitioner Henry Diana. In the first four events the pair worked together they finished no worse than T24, showcasing Diana’s immediate impact.
His form is trending in exactly the right direction and, with the caddie switch seemingly a good one, Hall could just throw his name in the hat for a surprise selection at the Ryder Cup in September.
From Warren, Ohio, the caddie previously worked with Stephen Jaeger, where he helped the German to a maiden PGA Tour win. That came at the Texas Children’s Houston Open in 2024.
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Currently based in St Simons Island, Georgia, Diana first started caddying back in 2002 and has enjoyed a long career.
As well as his previous gig with Jaeger, the American has carried the bag for other PGA Tour professionals such as Tom Hoge, Bill Haas, Colt Knost, Ben Crane, Cameron Beckman and Charles Howell III. It appears his longest partnership was with Howell III.
Although a caddie, Diana seems to have been quite the player before making the career change. He previously played for several years on the Nike Tour, now the Korn Ferry Tour.
He competed from 1993-1996, and then played in some events in 1998 and 2002, which is when he stopped playing. His best event when competing was T66 and his best finish was 53rd.
Before competing on the Nike Tour, the American attended the University of Alabama, where he played collegiate golf. It is an institution with a long and storied history when it comes to sports, producing the likes of Major winner Justin Thomas and former amateur PGA Tour victor, Nick Dunlap.
In a brief interview with The Caddie Network, Diana said the best thing about doing his job is “watching the best players in the world on a daily basis.”
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