He once walked off the course after an 81 at the Scottish Open with his curly hair twisted in a half-dozen directions, lamenting how he had to hit driver, driver and 1-iron simply to reach the par-5 sixth hole. And his mood did not lighten when a clueless reporter asked him, 'Monty, was the wind a factor?'
This was one year after Montgomerie shot 64, still the lowest score ever at Carnoustie.
That's the nature of most links courses. But Carnoustie is a mystery in other ways.
For most, the only memories of these mean ol' links are from 1999, when the rough was so high and the fairways so narrow that more than 100 scores were 80 or higher during the week. Sergio Garcia cried in his mother's arms after he shot 89-83 in his first major as a professional. The winning score of 290 was the highest at a British Open in more than 50 years.
The tabloids referred to it as Car-Nasty.
Eight years later, there might be reason to call the course Car-Nicely.
'This year, it's a different course,' Garcia said Wednesday. 'The rain is not helping, that's for sure. If we don't get some wind coming, the scores are going to be very low. It's going to be easy to get to the fairway. We're going to be able to stop it quite easily on the greens.'
No one is sure what to expect when the 136th British Open begins Thursday, with Tiger Woods trying to become the first player in 51 years to win the silver claret jug three straight times.
The fairways are wider. The rough is minimal, not enough to cover shoes in some spots.
The weather is the biggest wild card.
Monday began with heavy rain that fell sideways because of 30 mph gusts, and ended with brilliant blue skies. Tuesday began with glorious sunshine, only to have the course pelted with showers in the evening.
Constant rain in the United Kingdom over the last two months has made the crusty turf feel more like carpet in a five-star hotel. It's a complete turnaround from Royal Liverpool last year, which was so brown and baked that Woods only bothered to hit driver once in 72 holes.
The only consensus is that Carnoustie itself should be a fair test. Maybe the Royal & Ancient learned its lesson from last time.
Padraig Harrington believes the 24-year gap between Opens, from 1975 to 1999, left the R&A uncertain how much the game had changed. That might explain fairways that were only 12 yards wide and framed by knee-high grass.
'They obviously erred on the side of, 'Let's make it as tough as Carnoustie is meant to be.' This time around, they have the experience of '99 to know the golf course,' Harrington said.
But before anyone thinks this is a cupcake, Harrington issued a warning.
'You can come out here and play this course with no rough and it would still be a very difficult test,' he said.
Woods tied for seventh in 1999, four shots behind a playoff that included winner Paul Lawrie, Justin Leonard and Jean Van de Velde, the infamous Frenchman who threw away a three-shot lead with a triple bogey on the final hole.
Woods only hit balls on the practice range and putting green on Wednesday, a recent trend for him in the majors. He, too, has seen the many faces of Carnoustie, having playing the Scottish Open as a 19-year-old amateur in 1995.
So when it was suggested that Carnoustie might be a cupcake this time around, it was all he could do to contain a smirk.
'I've never heard anyone say Carnoustie is easy,' Woods said. 'Even the times I played the Scottish Open here, it was more benign than this, and the scores really weren't that low. There are so many holes where you're forced to hit long irons into the green. If you miss the ball in any of pot bunkers off the tee, you have to go sideways -- if you can.'
Part of the mystery will start to unravel Thursday.
There is not much wind in the forecast, but that means nothing. Ernie Els is staying across the Firth of Tay in St. Andrews this week, and he woke up the other day to see the flags limp on the Old Course. By the time in got to Carnoustie, the flags were whipping in the wind.
The Big Easy considers this the toughest links, a place where every shot gets tested. But as he spoke fondly of the length (7,421 yards) and the limitless bunkers, someone asked him where Carnoustie ranked for enjoyment.
'Enjoyment in a major? You enjoy a major afterward,' Els said. 'From Thursday to Sunday, it's hard work. And it's going to be the same here this week. It's going to be a very tough test. Whether you enjoy that or not depends on where you finish.'
Either way, it should be a chance to show the real Carnoustie.
Montgomerie has been playing this links course since he was a lad, and he believes this week will allow people to see Carnoustie as it was meant to be played, even though it can be drastically different from day to day, if not hour to hour.
'Carnoustie now will lose its tag of whatever it was quoted as by you guys,' he told reporters Wednesday. 'I think that it will be seen as what it is -- one of the toughest and best links courses that we have in the world. Anyone that scores 70 around here has to be commended any day, any conditions.'
What about a 64? Montgomerie paused and smiled.
'Sixty-four was bloody good,' he said.