So far, he's kept coming back for more. Jackson wraps up his 10th year with the team on Thursday night, when the Lakers and Boston Celtics play a deciding Game 7 of the NBA finals.
A victory by the Lakers would help Jackson extend his record to 11 titles.
It will be Jackson's first Game 7 in the finals.
"I can't imagine myself going through this again," he said Wednesday. "It's not only a lot of fun, but it's a lot of stress and pain and anxiety, etc. But it's something you get acclimated to."
So is the drama that has unfolded in recent summers on whether Jackson will or won't return to the bench. He's a lame duck, working the final year of his contract, with no word on a possible extension.
Jackson turns 65 in September. He has undergone two hip replacement operations since October 2006 — using a cane at various times — and walks with a noticeable hitch in his step. Unlike last season, though, he didn't miss any games this year for health reasons.
Told by a reporter that his health appears to be at its best for the first time in a while, he replied, "I dispute that, but it's still nice of you to say that.
"I think we have a built-in memory system in our bodies to forget — it's like mothers giving birth. Somehow they do it again even though it's one of the most difficult things to ever do."
Jackson typically decides whether to return after an offseason physical.
His 10 NBA titles are a record for a coach, and he has a history of winning them in threes. He guided the Bulls to three straight from 1991-93, and another three from 1996-98.
He first joined the Lakers in June 1999, and they took to him immediately, winning three consecutive championships. They lost to Detroit in the 2004 finals and to Boston two years ago before winning it all last year.
"I never anticipated still being a coach and searching for this," he said.
His five grown children plopped a hat on his head after the Lakers' clinching victory against Orlando last year, signifying his 10th title.
"It kind of sunk in, the remarkable ability to have had this amount of opportunities, which I'm very grateful for," he said.
"I've been fortunate to have very talented players and talented teams. Along with that is a lot of responsibility that's had to be met, and I'm grateful I've been able to do that with the support of a great staff and the staffs that I've had."
Now Jackson is poised to claim a second straight title, something that could reward him financially. He acknowledged there's a bonus in his contract, although he wouldn't confirm that it's for winning back-to-back championships.
"I wouldn't ever disclose what's in my contract, but I know that the rumor has come up and it's been around," he said, adding that he would use the bonus to find charities that he described as "very necessary in my life. That's one of the things that I made a promise to myself about."
Jackson is already the first coach in NBA history to lead a team to three straight titles three different times. If the Lakers win Thursday night, and his health holds up, he might be tempted to go for a fourth three-peat next year.
He was talking about his players, but Jackson could have been describing himself when he said, "It's about health, it's about being able to make it through the season in a good condition physically because what happens when you win a championship is you draw your innermost self out physically, spiritually, emotionally, mentally and recover, and next year to win it back-to-back is one of the most difficult things you'll ever do."
Jackson notched his 224th career playoff victory in Game 6 on Tuesday, moving him past hockey Hall of Famer Scotty Bowman (223) for the most postseason wins by any coach in North America's four major pro team sports — the NBA, NHL, NFL and Major League Baseball.
"That's a lot of wins," he said. "It's great to have been standing and have been able to have these kind of teams, just a wonderful factor. But it's not going to be any significant thing that I'm going to remember."