Who Is Rory’s Caddie? All about Harry Diamond

Rory McIlroy’s caddie is more than just a professional partner—he’s a lifelong friend. Harry Diamond, McIlroy’s best friend from childhood in Holywood, Co Down, has been on his bag since 2017.

While some initially viewed the partnership as temporary, their bond has only strengthened over the years, leading to multiple PGA Tour victories and two FedEx Cup titles.

The Friendship Behind the Bag

McIlroy and Diamond grew up together, playing golf at Holywood Golf Club. Diamond was a talented player in his own right, representing Ireland in his youth and even winning the 2012 West of Ireland Championship, which secured him a spot at that year’s Irish Open.

When McIlroy split with his longtime caddie JP Fitzgerald in 2017—after eight years and four Major wins—many expected him to bring in a seasoned caddie with more experience. Instead, he turned to Diamond, trusting their long-standing friendship and deep understanding of his game. Despite doubts, the duo has stuck together, winning nine PGA Tour events and two FedEx Cup titles (2019 and 2022).

A Brief Switch: Niall O’Connor Steps In

In 2022, Diamond briefly stepped away as his wife was expecting their second child. During this time, another friend, Niall O’Connor, took over caddie duties and helped McIlroy secure a win at the RBC Canadian Open. O’Connor, a former Ulster rugby player and keen golfer, had previously caddied for McIlroy at the 2019 DP World Championship in Dubai. However, once Diamond was ready to return, he reclaimed his spot on the bag.

McIlroy and Diamond’s Dynamic on the Course

McIlroy has often praised Diamond’s influence during key moments in tournaments. One standout example came at Quail Hollow when Diamond convinced McIlroy to take a penalty drop on the 72nd hole, leading to a smart play that helped secure victory.

“Harry was awesome out there, especially that decision on the last,” McIlroy said after the win. “I was ready to get in there and try to play that with a lob wedge, but he calmed me down, slowed me down, and said, ‘Pal, let’s just think about this.’ Ultimately, we made the right decision, and it’s probably been our best win together.”

While McIlroy and Diamond have enjoyed significant success, they have yet to win a Major together—a point often highlighted since McIlroy has been stuck on four Majors since 2014. However, their trust and chemistry on the course remain strong.

Life Beyond the Fairways

Diamond is known for keeping a low profile, avoiding social media and staying out of the limelight. Aside from caddying, he is believed to own several businesses, including bars. Off the course, his bond with McIlroy extends beyond golf—he was also the best man at McIlroy’s wedding to Erica Stoll in 2017.

How Much Does Harry Diamond Make?

As McIlroy’s caddie, Diamond is undoubtedly well compensated. McIlroy has one of the most lucrative bags in golf, with annual PGA Tour earnings ranging from $4-7 million. Typically, caddies receive around 10% of a player’s winnings, meaning Diamond likely earns a significant amount.

For context, McIlroy reportedly paid his former caddie, JP Fitzgerald, 10% of his massive $9 million FedEx Cup bonus in 2016, along with 10% of his Tour Championship earnings. In 2019, McIlroy won The Players Championship, taking home $2.25 million—meaning Diamond likely received a substantial cut.

Beyond the financial rewards, the perks of working for McIlroy include flying on private jets, staying in luxury accommodations, and sharing in the victories of one of golf’s biggest stars.

A Lasting Partnership

Despite criticism and ongoing questions about whether McIlroy should hire a more experienced caddie, he remains steadfast in his decision to keep Diamond by his side.

“I was an only child, and Harry was like a big brother to me,” McIlroy has said. “I love having him on the bag. I’m never going to give him sh** even if something goes wrong. It wouldn’t be worth it.”

While the duo continues to chase that elusive Major victory together, their partnership is built on more than just trophies—it’s a friendship that has stood the test of time.