He already has suffered enough.
The sometimes burly, often surly Scot should be positively chuffed with the British Open only a week away. Having gone 18 months without a trophy that belonged only to him, Montgomerie ended one of the longest dry spells of his career when his 6-iron somehow stayed out of the water on the 18th hole and he won the European Open by one shot.
It was his 31st victory on the European Tour, one more than Nick Faldo, trailing only Seve Ballesteros and Bernhard Langer. It came three weeks after he shot 82 in the U.S. Open to miss the cut, and two weeks after he turned 44.
'It is just great at 44 to come back and win again, as sometimes that is the end of one's career,' Montgomerie said. 'And I feel this is a new beginning for me, and I can look forward now.'
Forward, in this case, starts with the Scottish Open this week at Loch Lomond. The grand prize is a silver claret jug at Carnoustie, where Montgomerie believes he still has time to end his 0-for-62 drought in the majors.
But he might be kidding himself.
Since the Masters began in 1934, only six players have won their first major championship after turning 40, and none has nearly as much scar tissue as Montgomerie.
No other player has been runner-up five times in a major without eventually winning one.
Montgomerie was in a three-man playoff in the U.S. Open at Oakmont in 1994 when he wore dark clothes in 100-degree heat and wilted. He ran off three straight birdies at Riviera in the '95 PGA Championship to get into another playoff, only for Steve Elkington to win with a birdie on the first extra hole. There was Congressional in 1997, when Monty took forever over a 5-foot par putt on the 71st hole and missed, losing again to Ernie Els in the U.S. Open.
And last year at Winged Foot felt like root canal without Novocain.
Standing in the 18th fairway with a 7-iron in hand, Montgomerie chunked his approach and three-putted for double bogey, finishing one shot behind Geoff Ogilvy. It was the worst collapse at Winged Foot, even though Phil Mickelson's double bogey was more spectacular.
There have been other not-so-memorable moments at the majors.
Montgomerie was riding enormous support at Royal Lytham & St. Annes in 2001 until splitting his pants trying to hit a bunker shot. No less an authority than Jack Nicklaus proclaimed him the U.S. Open champion at Pebble Beach in 1992 when he finished a wind-blown final round ahead of the leaders, only to see Tom Kite pull through.
Here he comes again.
The Scottish flag will wave proudly along the links of Carnoustie as Brave Monty rides again.
'It will be a battle whether he can use the emotional momentum from being in Scotland and the great support he gets,' Nick Faldo said Tuesday. 'He's been there enough times, I'm sure there's got to be a couple that scarred him. But you never know with Monty. He's on a bounce-back. Maybe he'll ride the wave all week.'
There is precedence for guys winning their first major after 40, but the list is short.
Kite was 42 when he won the U.S. Open. He had gone 67 starts as a professional before winning his first major. But he had only three runner-up finishes, and his heartache was rarely his own doing.
Jerry Barber was the oldest first-time major winner since 1934, winning the 1961 PGA Championship at age 45. Safe to say he didn't carry the same burden as Brave Monty.
Roberto de Vicenzo was 44 when he captured the 1967 British Open, and that was a year before he couldn't keep score at the Masters. Julius Boros was 43 when he won his first major at the 1963 U.S. Open, and he became golf's oldest major champion when he added the PGA Championship five years later.
Mark O'Meara won the Masters and British Open at age 41 in 1998. Although O'Meara had won 14 times in a solid career, his name was never the first mentioned in any conversation of best to never win a major.
Mickelson and Montgomerie were the favorite targets.
Lefty was only 0-for-42 in the majors, minus the train wrecks. He plays golf with flair, winning or losing, but Mickelson never really collapsed in the biggest events. His two close calls before winning the 2004 Masters were the 1999 U.S. Open and the 2001 PGA Championship, and both times he was beaten by a par putt on the final hole. That's no disgrace.
Even though Monty had more baggage, he did not get as much scrutiny as Mickelson because he had never won in the United States. But his record stands tall, with seven straight Order of Merit titles in Europe, eight overall, and enormous success in the Ryder Cup.
He's coming off a victory he called 'very, very important,' but one has to wonder if even Montgomerie truly believes a major championship is in his future.
The last time the British Open was held at Carnoustie, he won the week before at Loch Lomond.
'How could I possibly feel any better than I do right now?' he said at the time. 'I can only go into the British Open with confidence, and that's what many players can't say.'
He was asked Sunday if he had doubts he would ever win again.
'Of course,' he replied. 'There will be a time where I will have my last win somewhere, and I will always remember it. I hope it is not this one, but if it is, I will savor this for the rest of my life.'
Yes, he is looking forward.
But he has reached a stage in his career where the greater joy might be looking behind.
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