Montgomerie is definately considered to be one of the best golfers never to have won a major championship, after finishing in second place on five separate occasions. During what most consider to be his best years in the 1990s Montgomerie had several close shaves. A third place at the  U.S. Open in 1992  at  was the first of these. He was prematurely congratulated by Jack Nicklaus who said “Congratulations on your first U.S. Open victory” to Monty after he finished the 18th hole on Sunday. Tom Kite who was still on the golf course when Montgomerie finished, ended up winning the championship.  I think Monty’s golfing career could have been a hell of a lot different if he had won at Pebble Beach

At the U.S.Open in 1994 , played at Oakmont Country Club, Montgomerie’s  bad luck continued as he lost in a three-man play-off to Ernie Els. Famously, Montgomerie was left with only one shirt to play in during the Monday playoff, a dark tartan design, which did not help his cause in the very hot playing conditions. He shot 78 to trail the 74s shot by Els and Roberts, with Els eventually winning at the 20th extra hole.

At the 1995 PGA Championship, Montgomerie amazingly birdied the final three holes of the Riviera Country Club course in the final round (which surprised everyone and made people think this was his time to shine) to tie Steve Elkington at 17 under par, which was a record low score in a major championship. On the first sudden-death playoff hole, after being in better position after two shots, Montgomerie missed his putt, while Elkington holed from 35 feet to claim the title.

Ernie Els once again got the better of Montgomerie at the  U.S. Open in 1997 played at Congressional Country Club. Montgomerie’s 65 in the opening round is considered to be one of the finest rounds in U.S. Open history, but a 76 in the second round brought him back to the field. A bogey on the 71st hole dropped Montgomerie one shot behind Els, who parred the last to win.

However, it was at the U.S. Open 2006, where Montgomerie had his best chance to win his elusive first major. He stood in the middle of the 18th fairway in the final round having sunk a 50-foot birdie putt on the previous hole, which put him in the outright  lead. While waiting in a perfect position on the 18th fairway for the group in front to clear the green.  Montgomerie switched his club from a 6-iron to a 7-iron, assuming adrenaline would kick in. Once the wait was over, he hit the approach shot poorly, ending up short and right of the green, in thick rough. He pitched onto the green, and then three-putted from 30 feet to lose the tournament by one stroke.  Montgomerie said, “At my age I’ve got to think positively. I’m 43 next week, and it’s nice I can come back to this tournament and do well again, and I look forward to coming back here again next year and trying another U.S. Open disaster.”

I’ve put Monty at number one because he has achieved about as much as it is possible to achieve in golf without winning a major, and in my opinion achieved more than a lot of other past major winners.