Rory McIlroy’s caddie Harry Diamond has raked in a small fortune alongside the Northern Irish superstar, but just how does his net worth compare to Tiger Woods’ legendary former bagman, Steve Williams? Spoiler alert: One’s busy counting his gold bars while the other is still digging through his piggy bank.
Rory McIlroy has finally conquered the demons of Augusta, snagging consecutive Masters titles. Only three others have enjoyed this elite status—so, naturally, they’re all rather jealous, and probably still holding a grudge.
While McIlroy basked in the limelight, also known as the “Rory Show,” his trusty sidekick and long-time pal, Harry Diamond, was enjoying a financial jubilee. Once merely a glorified bag carrier, a caddie’s responsibilities now include mental coaching and occasional on-course therapy sessions. Fee structure? Just a cool ten percent of the winnings, plus a tip if they don’t throw the clubs.
Diamond has flourished financially over the years, but let’s be honest—who could compete with Steve Williams, the caddie equivalent of a rock star? Billionaire mindset aside, Williams caddied for Woods during his prime and has a net worth that would make most people weep into their mortgage payments.
During his partnership with Tiger, Williams collected a wealth that would make Midas jealous, standing at an estimated $20 million (£15.7 million). While he was hauling in that cash, he was also the backstage pass holder for 13 of Woods’ 15 major victories. Just a casual day at the office, really.
In the golfing world of yore, Williams’ financial success ran parallel to Woods’ prowess—when Tiger brought home trophies like it was Black Friday, Williams found himself on an eternal shopping spree. Meanwhile, today’s caddies find themselves wondering what happened to their “early bird gets the worm” golden days.
Diamond, though he lacks Williams’ megastar status, has made a name for himself, quietly enjoying life in the spotlight. Since hitching his wagon to McIlroy in 2017, he’s gone from caddying for spare change to earning a cool $450,000 (£336,000) in just one Masters tournament alone. Not bad for channeling his inner sherpa while carrying around some fancy sticks!
The juxtaposition between Diamond and Williams illustrates the caddying universe is less about mere fortune but more about fame. Williams turned Tiger’s celebrity into his own brand—Diamond, however, is more like the reliable local handyman; always there, often underappreciated, yet incredibly indispensable. Though it’s clear that Williams is currently the financial heavyweight, with McIlroy’s resurgence in form, perhaps we’ll soon witness a Frodo and Gollum dynamic reshaping the riches of the caddy world.

