And this quest will take him back to where his career began.
Jackson has agreed to run the New York Knicks' front office and will be formally introduced by the team at a news conference at Madison Square Garden on Tuesday morning, a person familiar with the negotiations between the 11-time champion coach and the franchise told The Associated Press on Friday.
The person spoke on condition of anonymity because the Knicks would only confirm that a "major announcement" involving team executives was scheduled. Jackson also did not make any immediate public comment, but the move had been expected for several days - and was practically confirmed earlier this week by Knicks star Carmelo Anthony, who said he had heard the Hall of Fame coach was "coming on board."
Jackson had been courted by clubs before, and fans in Los Angeles clamored for him to return to coaching not long after he left the Lakers after the 2010-11 season. He's largely shunned limelight during this three-year break from work, during which he did things such as working on his health - arthritis pain hampered him toward the end of his coaching career - and released a book chronicling his basketball life.
Denver coach Brian Shaw, who played for Jackson and has been an assistant under him as well, said Friday that he would not be surprised to see one of his mentors take on the challenge of rebuilding the Knicks.
"I think he's a basketball lifer, a basketball junkie," Shaw said in Miami, where the Nuggets were playing the Heat. "I think that with all the success that he's had, what he's learned and his passion for the game, I think it gets boring when you do something like he's done all his life and all of a sudden you're kind of out of the mix. If he does do it, he'd be excited about the challenge of attacking the game from a different position."
Jackson played his first 10 NBA seasons with the Knicks - he was there for 11 actually, missing the 1969-70 championship season because of injury. Jackson was a key part of the 1972-73 team that won the NBA title, topping the Lakers.
New York hasn't won a championship since. Jackson has won 11 since, six with the Chicago Bulls and five more with the Lakers.
Shaw has spoken with Jackson regularly during the season, saying that his former coach will sometimes call or text to ask if a play the Nuggets run was one that they used together during their triangle-offense days. But Shaw - who will likely be mentioned as a potential coaching candidate in New York if the Knicks decide to part ways with Mike Woodson - has kept his distance from Jackson during this will-he-or-won't-he process.
"I've kind of left him alone during this period of time because I know it's a lot going on and certainly people are hitting him from every different direction," Shaw said.
Odds are, that won't change anytime soon.
Jackson's arrival in New York will likely usher in a new era for the Knicks, who may miss the playoffs this season after winning 54 games a year ago. Even NBA Commissioner Adam Silver said earlier this week that he wanted to see Jackson back in the game, saying "the league needs him."
Apparently, the Knicks felt they needed him as well.
New York could lose Anthony this summer through free agency, will likely look to upgrade their roster in several other areas, and Jackson will have to tackle all those issues - and plenty of others - even though the Knicks have spent about as freely as any team in recent years. And a playoff trip this year is hardly a certainty, with the Knicks currently on the outside of the postseason picture.
With the Bulls, he had Michael Jordan and Scottie Pippen. With the Lakers, he had Shaquille O'Neal and Kobe Bryant.
With the Knicks, he'll have more questions than answers, at least in the beginning of his first foray into life as an executive. There's also the issue of how much power he'll actually have working for Madison Square Garden chairman James Dolan. Since the start of the 2004-05 season, the Knicks have gone through six head coaches and won a total of seven playoff games.
Starting Tuesday, it'll apparently be Jackson's job to change all that.