On the course, since being crowned the European No1 for the fifth time, Montgomerie has earned $300,000 in winning the Hassan Trophy and the individual event at the World Cup, where Scotland were runners-up. He is not finished.
The house in Surrey he bought in the summer could receive further investment if he scoops the $2m on offer in his last two events before a two-month break. This week he defends his Million Dollar title at Sun City, while in the the New Year are the Andersen Consulting World Championship finals.
Montgomerie faces his nemesis, Ernie Els, in his Arizona semi-final. Els has twice beaten the Scot at the US Open and in the World Match Play. So Montgomerie's play-off win over the South African at Sun City last year was highly significant. "It was huge," he said.
"I have earned his respect and that is important to me. Although he is younger, he, Tiger Woods and Greg Norman are at the top of the tree. He will be looking for me now as I look for him. It was nice to win the World Cup individual with him in the field."
Montgomerie had finished 11th out of 12 at Sun City in his two previous outings. "I went out just to enjoy it but I play my best golf when I am relaxed," he said. Trying to be relaxed at a major championship, the one ingredient missing from his CV, is still his biggest challenge.
"It's a Catch-22, isn't it? I have put importance on majors by arranging my schedule for next year around them, but I think in the past someone like [Nick] Faldo has put too much pressure on the majors. I need to go into them as if they were a Slaley Hall or an Irish Open.
"Now I know I don't need to play at 100 per cent. I can win a major with 85 per cent of my game. Knowing that should help me to relax."
- Andy Farrell