Speaking in an in-depth interview with Golf.com, Montgomerie spoke at length about Woods and his impact on the game and, despite being majorless, said he had no regrets about his career.
“I never won a major,” he said. “Tiger won 14. But would I trade my career for Tiger’s? No. I started out this game a pretty good golfer and finished in the Hall of Fame. I feel I have overachieved.
“So how could I say I wish it were better? People will say,`Well, he didn’t win a major.’ And, yes, I would have liked to shut them up by winning one. But that’s my only regret, really.
“Great that I have won senior majors, which has quieted the odd person.”
The 53-year-old Scot, who has five runner-up finishes in majors, also revealed that he enjoys what tour life brings, whereas he isn’t so sure that Woods feels the same.
“I’ve made mistakes,” he said. “We all make mistakes. But I’ve had a long career. I don’t think Tiger will be out here at 53. He might say, `I don’t need the money.’ But it’s not just money.
“It’s self-esteem. Self-esteem is huge in life. You walk a wee bit taller, having done something well. I like this life. I like meeting new people. I like the travel. I love the life. Whether it’s for everybody, I can’t say. If Tiger loved the life, I can’t say.”
And, speaking from his own experiences, Colin Montgomerie, who finished runner-up to Woods at the 2005 Open at St Andrews, believes Woods would have eclipsed Jack Nicklaus’ record of 18 majors had he had a settled private life.
“Nineteen has been such a focus for him,” he added. “If Tiger had his children with him full-time, a wife, a settled home, he could have got to 18, to 19.
“I know from my own life how hard it is to play golf when your life at home is not settled.
“After that Thanksgiving night changed everything, he no longer had a private life. A private life by the term itself is a private life. You have a public life and a private life. “And when the private life becomes public, it’s dangerous. It hurt. It hurt him. It hurt the game of golf.”