“He’s been like a big brother to me the whole way through my life,” Rory McIlroy confessed through tears about the man who has been in as much pain as he has for the past 11 years. For the Northern Irish star, his caddie Harry Diamond isn’t just the person who’s carried his bags. He witnessed it all. He was there as the best man when McIlroy got married in 2017. He was there every time McIlroy would find himself desolate and wondering what went wrong. Through the countless “treatments”—hypnosis, books, self-improvement podcasts, and exposure therapy among others—the recent Masters victor took up, the caddie would patiently wait in the shadows, motivating, helping, and protecting his best friend whenever needed. Unfortunately though, he’s never been able to get the same kind of protection back…

Despite McIlroy’s fiercest efforts to shield Diamond, cracks would surface often and deeper than the last time. Sometimes as a lone voice after a missed putt—“Blame your caddie!” to which the golfer would hit back with “Shut the f*** up”—or as harsh critiques dissecting Harry’s “poor” caddying over hour-long podcast episodes. One thing was clear: Harry Diamond had become public enemy No. 1. People would complain he didn’t know the sport enough, despite his 2012 West of Ireland Championship win and 2011 North of Ireland Championship runner-up finish. One would advise Steve Williams to replace Diamond, while another would bring up Matt Fitzpatrick’s old caddie Billy Foster’s name. McIlroy could only wait and watch, bidding his time.

Last Sunday, that chance finally came with a career Grand Slam. And the golfing veteran made sure the world knew about the man who made it possible. “To be able to share this with him after all the close calls that we’ve had, all the cr-p that he’s had to take from people that don’t know anything about the game, yeah, this one is just as much his as it is mine. I couldn’t think of anyone better to share it with than him.” Well, win and respect aside, Harry Diamond also took home something else that day, which we’ll now tell you about…

Talking about salaries, the standard arrangement for top caddies includes a weekly base salary plus performance bonuses. Diamond reportedly earns $3,000-$4,000 weekly regardless of tournament outcome. But the real money comes from their golfer’s success: 10% for wins, 7% for top-10 finishes, and 5% for making cuts.

So, when Rory McIlroy sank that dramatic playoff putt at Augusta National, his caddie Harry Diamond didn’t just celebrate a Masters victory; he also pocketed a staggering $420,000 bonus from McIlroy’s $4.2 million Masters victory. This adds to an already impressive 2025 for the caddie. Reports indicate he had earned between $870,000-$900,000 in bonuses from McIlroy’s earlier wins this year alone. Meaning? With a net worth of around $2.5 million, Diamond is already one of the wealthiest caddies in the PGA Tour.

But what does carrying the bag for a champion like McIlroy involve? Beyond the paychecks, Diamond’s role demands dedication and a unique skill set.

Life on tour demands meticulous preparation and mental strength

Rather than pursuing a playing career, Diamond worked in his family’s property business, managing hotels and restaurants in Belfast and Bangor.

In 2017, he replaced McIlroy’s previous caddie, J.P. Fitzgerald, who had been with him since turning professional. Many considered it a temporary arrangement, but they’ve remained together ever since. Diamond’s tournament routine reveals the demanding life of a top caddie. He typically arrives at venues a day before McIlroy to walk the course alone. This advanced preparation allows him to study layouts, analyze pin positions, and identify potential challenges.

He meticulously notes course conditions, green speeds, and strategic options. During competition rounds, Diamond maintains a calm demeanor that complements McIlroy’s more emotional approach. His communication style isn’t as vocal as other caddies, but his words carry weight at crucial moments.

After McIlroy missed a short putt that would have won the Masters outright, Diamond provided perfect perspective. “Well, Pal, we would have taken this on Monday morning,” he said simply. This straightforward encouragement helped McIlroy reset mentally before the playoff.

Diamond’s understanding of McIlroy’s personality comes from their decades-long friendship. He knows when to speak up and when to stay quiet. This emotional intelligence proves just as valuable as course knowledge in high-pressure situations.

Their Masters’ triumph represents more than just financial reward. It vindicates their partnership and friendship against years of doubt from outsiders. For Diamond, the $420,000 payday surely feels sweet, but helping his childhood friend complete the career Grand Slam? That’s truly priceless.

What experience or qualities do you think are most important in a successful caddie-player relationship? Let us know in the comments section below!