Rory McIlroy has officially exorcised his Augusta demons by clinching back-to-back Masters titles, becoming just the fourth man in history to do so. The Northern Irishman spent most of the weekend at the top of the leaderboards before ultimately holding off Scottie Scheffler to claim his second green jacket.
But while McIlroy took the headlines, the man standing over his shoulder, Harry Diamond, was also reaping the rewards of a historic afternoon. The role of the caddie has evolved from a humble bag-carrier to a high-stakes partnership, and nowhere is this more evident than in the bank accounts of the men who guide the world’s best. Diamond, a childhood friend of McIlroy, has seen his own net worth skyrocket after years alongside Rory. But even his impressive earnings face stiff competition from the gold standard of the profession: Tiger Woods’ legendary former bagman, Steve Williams.
The New Zealander, who served as Woods’ right-hand man between 1999 and 2011, reached a level of financial success previously unheard of in the profession. He was on the bag for 13 of Tiger’s 15 major championships.
During that period of unprecedented dominance, he amassed an absolute fortune. Reports estimate Williams’ net worth at roughly $20million (£15.7m). At the height of “Tiger-mania,” he was earning enough through prize money percentages and personal endorsements to be ranked among the highest-paid sportspeople in his home country.
His wealth was a direct reflection of Woods’ win rate, which often hovered around 30 per cent – a statistic that modern pros can only dream of. While Joe LaCava also earned millions during Tiger’s later career, including the emotional 2019 Masters win, it is the Williams era that remains the benchmark for caddie earnings.
Since taking the bag for McIlroy full-time in 2017, Harry Diamond has often faced scrutiny from critics – particularly during the latter years of McIlroy’s decade-long wait for a fifth major – but the 2025 Masters victory silenced the doubters and the 2026 triumph only reinforced his value.
With caddies typically receiving 10 per cent of a win and around seven per cent for a top-10 finish, Diamond’s consistent tenure with a top-ranked player has made him a very wealthy man. Estimates suggest his career earnings with McIlroy have now surpassed €10m (£8.5m).
The comparison between Diamond and Williams highlights how the role has changed. Williams operated in an era where he was almost as much of a celebrity as the players, leveraging Tiger’s fame into his own personal brand.
In contrast, Diamond represents the quiet professional – the trusted confidant who provides a level of comfort that McIlroy claims “probably no one else in the world could.”
While Williams holds the record for the highest net worth, Diamond is rapidly closing the gap, and if McIlroy’s major-winning form continues, we may soon have a new record holder on our hands.