‘Rory could be haunted for life, like I am – but caddie cost him’

A winner of eight European Order of Merit titles, including seven on the trot, and unbeatable in Ryder Cup singles, he was also a runner-up at the majors on five occasions. The one that cut the deepest wound was also at the US Open, back in 2006, when he had split the fairway on the last while needing a par for a win. The subsequent seven-iron elicited a comment that spoke for everyone from pained club hackers to the Pinehurst McIlroy: “What kind of shot is that?” He missed the green and took three putts for a double bogey. Even a bogey would have got him into the play-off. Phil Mickelson also took a six. Geoff Ogilvy won.

“I don’t think I ever recovered from 2006,” Montgomerie says on a bright day on the balcony at Wentworth Golf Club. “I never contended at the majors again. I was getting towards the end of my span and had a feeling that was it, that was the best chance I was going to have.

“Knowing the standard of golf being played, knowing Tiger was taking two a year, there wasn’t much left.”

He left Winged Foot in the same way that McIlroy left Pinehurst, namely in a hurry. And he also knows what it is like to play while others rake over your private life. “I understand him not talking to the press,” Montgomerie says of McIlroy. “There is nothing to say apart from negativity. What could he say other than, ‘I threw it away?’ Ten years of hurt and ten years of hell in trying to win another came out at the end.

“I thought he was actually very dignified. He didn’t slam doors and rev away. I left Winged Foot and felt I’d let myself down. People wanted me to win a major and I’d let them down, too. I think Rory feels that way, too.”

Montgomerie’s near miss in 2006 involved a long delay on that final fairway as Vijay Singh negotiated a drop. He says he began to think too much and changed clubs from a six to a seven-iron. The last swing was hesitant. “Damn, damn and damn again,” he wrote in his autobiography. It was not the one that got away. It was the one he had let go.

McIlroy fell short at Pinehurst last month after dropping three shots in his final four holes

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McIlroy’s collapse also started when he chose a seven-iron, on the par-three 15th. “That was the wrong club because the adrenaline was beginning to pump,” Montgomerie says. “It was a good four [bogey] in the end, but the killer was 16 [a bogey five]. The stat came up — 496 in a row [putts made] from inside three feet that year. He did not just miss, though, he missed badly.

“I try to analyse it. Was he getting ahead of himself for the first time? He knew 16 was a difficult hole and he had done the hard work. Did he switch off? It would have been an incredible victory with what’s been going on off the course as well as on it, and how he’s been used as this anti-LIV spokesman for two years.”

This week McIlroy defended his caddie, Harry Diamond, but Montgomerie says taking a driver on the par-four 18th was a clear error. “He hadn’t done it all week and the caddie should have stopped him. Bryson was missing every fairway, the worst in the field on Sunday. At the end, he was just thrashing it and it was a long drive competition. What a bunker shot, of course, but he got the luck and Rory didn’t.”

Montgomerie feels that Diamond, right, should have stopped McIlroy using his driver on the 18th at Pinehurst. A bogey five cost him a play-off with DeChambeau

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Montgomerie was pushing 43 at Winged Foot. McIlroy is 35 and carded a 65 in his first competitive round back at the Scottish Open on Thursday, but the real test is next week. Troon may provide a tourniquet, but Montgomerie fears it has come too soon.

“[Nick] Faldo said something on the commentary and I agree — if he does not win another major this could haunt him for the rest of his life, not just career,” Montgomerie says. “I went to bed that night feeling very sad. I didn’t want to see the celebrations — I felt more for Rory than I felt for Bryson. If he gets into contention at Troon from where he was, it will be a herculean effort.”

Troon will be special for Montgomerie, whatever the outcome. He grew up on South Beach Road, some five doors from the course. His father, James, used to be the captain and, after a sojourn down south, the club secretary. James is sufficiently steeped in golfing lore to have seen Henry Cotton win at Muirfield in 1948 and once noted that King George VI circled the course accompanied by only two policemen.

Montgomerie Jr had planned to try to qualify this year, but scheduling on the PGA Tour Champions and realism did for that dream. “I qualified for Troon the last time in 2016 and wore compression socks for the last round,” he says. “Making the cut was a good way to finish and Troon is much longer than 2016.

“I’ve had my day. I can compete on the Champions Tour and they’re all 7,000 yards, not pitch and putt, but I’m not playing guys who are 320 yards in the air.”

Montgomerie finished runner-up at five majors, but could never quite get over the line

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Montgomerie moved to West Yorkshire when he was eight because of his father’s job in biscuits, and was tutored by Bill Ferguson at Ilkley Golf Club. Both his parents were captains. Over a cup of coffee he offers me a wonderful family heirloom.

“My grandfather invented the Penguin biscuit,” he says. “And the Blue Riband.” More biscuit talk ensues and it turns out James’s job with Fox’s Biscuits came with four season tickets to Leeds United. Montgomerie remains a well-informed fan and devotee of Argentine eccentric Marcelo Bielsa, who took the club into the Premier League. He even bought one of the giant buckets that the club sold in honour of the manager’s favoured means of watching matches.

“It cost £82,” he says, eyes widening. “There was one left and I told the guy in the shop to save it. I gave my name. He had no idea who I was.

A big Leeds fan, Montgomerie paid £82 for one of Bielsa’s famous buckets — and took a four-hour drive to Elland Road to pick it up

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“I drove four hours up to Elland Road but couldn’t get it into the boot, so I strapped it in the passenger seat. It must have looked a bit odd.”

Montgomerie felt Bielsa was a kind of genius despite many pundits criticising him, and getting the most out of talent is a theme. Montgomerie is old and wise enough to take the “best-player-never-to-have-won-a-major” tag as a compliment now although he admits sometimes he thought “Christ!” but he does have his three senior major wins as solace, and plays in the Senior Open at Carnoustie the week after Troon.

Knowing when time is up is hard to gauge. Tiger Woods, now morphing into his own tribute act, is a case in point, and Montgomerie would rather remember the man who beat him into another second place by five strokes at the 2005 Open at St Andrews.

“I hope people remember Tiger as Tiger was, the passion and the charismatic aura around him. There is none of that now. At Pinehurst he did not seem to enjoy a single shot and you think, ‘What the hell is he doing?’ He’s coming to Troon and he won’t enjoy it there either.”

Woods, 48, has long said he will call it a day when he is no longer competitive, to which Montgomerie says: “Aren’t we there? I’d have thought we were past there. There is a time for all sportsmen to say goodbye, but it’s very difficult to tell Tiger it’s time to go. Obviously, he still feels he can win. We are more realistic.”

This is not said with any sort of glee, but a sorrow that a new generation may be seeing him tarnish his legacy. “These guys only know Tiger Woods missing the cut and he’s better than that, the best we’ve ever seen.”

Montgomerie isn’t hopeful of European success at next year’s Ryder Cup in New York — “I don’t think we will be allowed to win there. Someone will come on and steal a golf ball or something”

TIMES PHOTOGRAPHER MARC ASPLAND

Montgomerie’s passion remains undimmed by the taunts of time, or of others. He was an emotional player who could be tetchy-feely when it came to spectators, and he remembers fondly how Payne Stewart waded into the crowd at the rowdy Ryder Cup in Brookline in 1999 and pointed out some of the worst hecklers.

“It was to the detriment of his own game and I said, ‘Payne, you’ve got yourself to think about’. Stewart then told Montgomerie to pick up his putt on the last. “And seven weeks later he was gone [in a plane crash],” he says with a sigh of lingering disbelief.

So what about Bethpage Black next year? “God almighty!” he says. “We desperately need an away win in the Ryder Cup, but I don’t think it’s going to happen in New York. I don’t think we will be allowed to win there. Someone will come on and steal a golf ball or something. It’s a drinking culture in America.”

But first it is the Open, on Montgomerie’s old turf, where more stories will be unfurled; some good, some bad and, if we get lucky, some that may be retold for decades. Greats such as Arnold Palmer and Tom Watson have won there, along with rank outsiders like Todd Hamilton. “What Rory has just proved is how bloody difficult it is to win any major,” says the man heading home.

Colin Montgomerie has collaborated with Loch Lomond Whiskies to create the Open Special Edition