It all started with him being front and center during the NBA lockout as the president of the players' union. It grew more complicated when the Los Angeles Lakers traded him away after he'd won five championships with the franchise.
Fisher signed on with Oklahoma City, and he's three wins away from achieving his ultimate goal of winning a sixth title. Only 13 players in NBA history have been a part of that many championship teams.
"What it would mean to win a championship means enough by itself without adding what has happened before now," Fisher said. "I think for this particular team and group of guys, this particular organization, there's a lot of meaning that would come from us finding a way to win three more games. So, that's primarily my focus right now. And then for me personally, there are a number of things I just won't choose to reflect on or look into until after this is long done and I can step away from things for a minute."
Fisher was heavily involved in the league's labor dispute, engaging in the conference room discussions that eventually were able to save a season that was in peril. His season took an unsettling turn when the Lakers unexpectedly traded him to Houston and he decided not to go.
Instead, he looked around to identify teams he thought gave him the best chance to win a title and he settled with the Thunder.
Even then, the turbulence wasn't over. The leadership of the NBA Players Association asked for Fisher to resign as president in April, and he refused while questioning the union's business practices under executive director Billy Hunter.
That dispute still looms as Fisher and the Thunder prepare to play Game 3 of the NBA Finals on Sunday night in Miami, with the series tied 1-1. Fisher doesn't expect any resolution until later this summer and he has done his best to keep his sights on the playoffs.
"All in all, for me, these are good problems to have. When you think about how tough it is for people every day, this is not hard at all to be able to try to figure out a way to be able to focus on playing basketball," Fisher said. "I'm healthy. My family's healthy. So at the end of the day, if these are the things that I have to deal with to be called tough days, I'll take it."
While Fisher wasn't pleased with how the Lakers handled shipping him out, he made the best of the situation by joining the Thunder -- who would eventually eliminate L.A. in the second round of the playoffs. Fisher spent all but three of his first 15 years in the league with the Lakers, winning a handful of championships.
Of the players to win at least six championships, nine -- including all-time leaders Bill Russell (11) and Sam Jones (10) -- played with the Celtics during their dynasty in the 1950s and '60s. The others are former Fisher teammate Robert Horry (7), Kareem Abdul-Jabbar (6), Michael Jordan (6) and Scottie Pippen (6).
"This is his eighth NBA Finals in 16 years. As a player you wish you can get there once," Thunder coach Scott Brooks said.
"A lot of players have never been there, and he has five championships."
Fisher said he considers Horry -- who won titles with the Lakers, Spurs and Rockets -- in a "stratosphere all alone." And he says he's not going to rub it in if he's able to win another title and surpass longtime teammate Kobe Bryant, who remains his friend.
"To me, it's kind of sacred ground," Fisher said. "I'm not going there. Some people will but not me."
Yet he still has something to prove.
Once he signed with Oklahoma City, he chose the jersey No. 37 -- the same as his age -- to highlight that his advancing years would not be a factor. Brooks says he's still making important contributions on and off the floor.
"I've never been around a player that communicates as well as he does with his teammates, never have. The guy has an incredible knack for saying the right things at the right times," he said. "He's helping this team win this year, and he's going to help this team win many years with all the things that they've took from him this past two or three months."
Whether Fisher will remain with Oklahoma City remains to be seen.
"I'm for sure enjoying my time here. I know for sure that I want to play beyond this year but from there, I haven't put a lot of pressure on myself about thinking about where that is and how that's going to happen," Fisher said. "Next year is so far away until we figure out a way to win that trophy. Once you win it, of course, the first question out of somebody here will be, 'Can you guys do it again? And what's going to happen?' That part comes after the job is done and right now we still have a big job ahead of us to try to figure out how to win three more games."