When you buy through links on our articles, Future and its syndication partners may earn a commission.
Harry Diamond had some important words for Rory McIlroy before his Masters playoff against Justin Rose. | Credit: Getty Images
Rory McIlroy’s glittering career is going from strength to strength, with the Northern Irishman accumulating a near-endless list of accolades and achievements.
The huge success he has enjoyed in the latest phase of his career is partly down to the man who has been on his bag since 2017, his best friend, Harry Diamond.
Diamond was alongside McIlroy at the scene of his greatest triumph, when he overcame Justin Rose in the first playoff hole to win the 2025 Masters and complete the Career Grand Slam.
McIlroy won the playoff after a draining afternoon | Credit: Getty Images
That came at the end of a draining afternoon that saw McIlroy squander a two-stroke lead early on, before regaining it and stretching the advantage to four, then, agonizingly, bogeying the 18th to miss out on the Green Jacket in regulation.
Despite their huge success, one thing McIlroy and Diamond had never achieved together was a Major title, with numerous heartbreaking near misses over the years.
As McIlroy faced the prospect of a playoff, surely he’d have had a fleeting thought that, once again, he might be denied, and this time in the most devastating manner of all.
That’s when Diamond stepped in with eight words that proved crucial at the most consequential moment of McIlroy’s career: “We would have taken this on Monday morning.”
Afterwards, McIlroy said: “I’m like, ‘Yeah, absolutely we would have.’ That was an easy reset. He basically said to me, ‘Look, you would have given your right arm to be in a playoff at the start of the week.’ So that reframed it a little bit for me.”
We all know what happened next, as McIlroy steadied his nerves with a birdie to finally give him the Masters title – the last of the four Majors he needed to complete the set.
Harry Diamond caddie for Rory McIlroy since 2017 | Credit: Getty Images
For any player, having the steadying influence of a man like Diamond would surely be invaluable, particularly at such a pivotal moment, but for McIlroy, their relationship goes even deeper than that.
McIlroy is well-known as a man who wears his heart on his sleeve, and that is no exception when it comes to his bond with Diamond.
When he returned to Augusta National to defend his title, he explained exactly what Diamond means to him.
“As an only child, he was like the big brother I never had, and I think that’s what makes it so special,” he said.
“Harry’s got a little brother and a big sister, so he had that, but I always felt like Harry was my big brother. I think that’s why, when I talk about it or – it’s why it makes me emotional.”
Credit: Getty Images
After two rounds of the 2026 Masters, the pair were creating magic again, with McIlroy six clear – the largest 36-hole lead in the tournament’s history.
With that huge advantage, it seemed almost certain that, over the closing 36 holes, McIlroy was set for a more comfortable time of it than a year ago.
There’s one thing for sure, though: if McIlroy does need some steadying words over the closing two rounds, in Diamond, he has the right man alongside him to deliver them.