"People don't understand the pressures of the Ryder Cup," he said. "I didn't until I played. The major championships are easy by comparison."
Major championships? Easy? Had the words come from any other player you would be entitled to scoff, but they deserve a certain respect when they are said by a man who endured the torments Montgomerie went through in his frustrating and ultimately fruitless attempts to join the ranks of golfing greats.
But then he did experience the most remarkable introduction to the biennial Transatlantic competition. It was 1991, Kiawah Island, the year of the War on the Shore. In the wake of the first Gulf War, American jingoism had reached the height of crassness, with the US players sporting Desert Storm baseball hats, refusing to meet Bill Clinton on the basis he had been a draft dodger and claiming, as one of their number did, that they would "whup Europe's asses" just like they had "whupped Iraq".
Montgomerie was an innocent abroad that year, the newcomer in a side that boasted the names of such giants of European golf as Ian Woosnam, Nick Faldo, Bernhard Langer and Seve Ballesteros. Yet he was to play a critical part in the competition's concluding drama.
Four down through 14 holes in his singles tussle with Mark Calcavecchia, he won the last four holes to square the match. Had Langer not missed a five-foot putt in his decisive game with Hale Irwin to give the USA the narrowest win then Montgomerie would have been hailed the hero of the hour.
Fast forward to two years ago at Celtic Manor. Montgomerie is now Europe's captain, but the rules of the game haven't changed. Which is to say the margin between winning and losing is still absurdly narrow. On this occasion, the European team seemed to be coasting after the fourball and foursome matches, but a stunning fightback on the final day brings the USA surging back into contention. Europe's win is sealed only on the penultimate hole of the last singles pairing when Hunter Mahan's duffed chip gives Graeme McDowell a 3&1 win.
Any sensible fellow would pay good money to avoid such things, but the world's top golfers, the most conspicuously acquisitive individuals in sport, forgo all financial reward for the uniquely exquisite agonies of the Ryder Cup. Men who wouldn't cross the road for less than a six-figure cheque willingly endure an emotional roller-coaster for a 50/50 chance that their abiding memories of the experience will be pain and humiliation. Just ask Mahan, who was left blubbering like a baby after his error two years ago.
Mahan missed out on his shot at redemption when USA captain Davis Love III named his wild-card selections for this year's event, which gets under way on Friday. Never the most exciting player himself, he has favoured the Steady Eddies of American golf with his picks: Steve Stricker, Jim Furyk, Dustin Johnson and Brandt Snedeker.
Belgium's Nicolas Colsaerts is the only Ryder Cup rookie in Europe's team, while Love has four in his side, but it is always easier for the home side to carry inexperience.
The pairings will be fascinating. Should the captains cobble together partnerships based on established friendships or take the risk, as Hal Sutton famously did with Phil Mickelson and Tiger Woods in 2004, that a sense of common purpose might lead to the burying of old hatchets?
Europe captain Jose Maria Olazabal, would do well to unearth a partnership as productive as the one he formed with Seve Ballesteros. The two Spaniards combined to claim 11 victories – a Ryder Cup record – in 15 outings together.
Olazabal will presumably not hesitate to reunite Sergio Garcia, back on the team after missing the last two Ryder Cups, with Luke Donald. Nor will he lose sleep before pencilling in Graeme McDowell beside Rory McIlroy. Paul Lawrie and Lee Westwood have the kind of well-measured games and temperaments that allow them to work with just about any other player, and Olazabal will cherish such versatility.
With 17 of the world's top 20 players involved, the quality of the field is hardly open to question. Whether Medinah is worthy of them is a little more open to doubt. At 7600 yards, it is more obviously a bomber's course than one for the shotmakers. The respected course architect Tom Doak called it "a maximum security prison".
To its credit, Medinah at least has some worthy history attached, an accusation you would hesitate to level at some recent venues. It will, however, have a Chicago crowd, so at least it should have an atmosphere befitting the event.
And the winners? Almost too tight to call. Nick Faldo has suggested a 14-14 draw could be on the cards, and he may be nearer the mark on that than he was with any of his strategies as losing captain at Valhalla in 2008. If it does finish all square, then Europe will hang on to the trophy they won amidst such emotional scenes in Wales two years ago. Olazabal, however, will be looking for a rather more emphatic result.
Contextual targeting label: