Phil Jackson won't have much to prove if he returns to an NBA sideline next season, but if he gets his wish and rejoins the league as a front-office executive, he'll be faced with a slew of new challenges that could give him an opportunity to fill in the few remaining blanks on his historically great resume.
With 11 championships rings and a reputation as one of the single greatest coaches in the history of professional sports, it shouldn't be a surprise that Jackson is reportedly not interested in coming back to the league as a coach.
He's got almost nothing to gain from a return to the sidelines.
Sure, if you wanted to nitpick, you could point to the fact that Jackson has never shown the ability to take a mediocre team and turn it into a great one. But that knock on his legacy ignores the fact that what Jackson did so often—took a great, star-laden team and kept it on a championship level for years at a time—might actually be the more difficult and impressive accomplishment.
After all, the egos, expectations and pressure of the situations Jackson faced in Chicago and Los Angeles required an extremely delicate touch. Relatively speaking, it's easy to take a decent team and turn it into a playoff contender when expectations are low. But what Jackson did by consistently winning when everyone expected—even demanded—success, was far more difficult.
That's all a long way of saying that Jackson has been to the mountaintop as a coach. So even though he might be susceptible to some shortsighted criticism that he hasn't won with anything but superstars on his roster, he's satisfied with his legacy as the NBA coach who brought multiple championships to the two franchises that employed him.
But now Jackson's working for the Detroit Pistons in a limited capacity as an adviser in their coaching search, and teams like the Toronto Raptors are reaching out to him with offers of management positions.
So if Jackson does opt to rejoin an NBA team as an executive (which he appears ready to do), he'll have plenty to prove.
For starters, he'll have to show that he's got an eye for acquiring talent.
The teams Jackson coached were largely ready-made by the time he arrived. The Chicago Bulls already had Michael Jordan and Scottie Pippen when he took over the reins in 1989. And the Los Angeles Lakers were stocked with plenty of stars 10 years later when Jackson assumed head coaching duties in his second stop. In fact, he probably would never have even considered joining the Lakers if Kobe Bryant and Shaquille O'Neal weren't already in place.
If there's anything we do know about Jackson's skills as a personnel evaluator, it's that he's got a keen eye for the obvious. He knows stars when he sees them on the court—and in the executive suite.
GM Jerry Krause put together the talent in Chicago, and Jerry West did the same in L.A. Jackson clearly learned the value of a good talent accumulator like Krause in his first stop, so he made sure to join forces with another in his second one.
So if there's another judgment we can make about Jackson's evaluative skills, it's that he knows which general managers to work for.
The ability to recognize good situations and subsequently turn them into great ones has been at the heart of Jackson's success. But it's quite another thing to start from scratch and create those "good" situations himself.
To do that, Jackson will have to prove that he can evaluate young talent and spot stars before they've established themselves as such. His reliance on veterans with the Bulls and Lakers doesn't give us much of an idea of whether he's capable of doing that.
There are plenty of other questions the Zen Master will have to answer as well if he does rejoin the league in some executive capacity: Will his ability to establish cohesion among players on the court translate to other executives in the front office?
Does he have the restraint to stay off the sidelines if he feels he could be running the team more effectively than whichever coach he picks to do the job? That one proved difficult for Pat Riley in Miami (just ask Stan Van Gundy).
And perhaps most importantly, can he retain the kind of drive he'll need to be successful without immersing himself in the day-to-day battles on the court and the camaraderie in the locker room? Coaches feed off the energy of their players, and there's a sense of accountability that comes from fighting alongside the guys in uniform.
Will that same urgency and accountability be there if Jackson is observing games from the luxury box?
It's probably a fool's errand to bet against Jackson succeeding; if he's shown us anything throughout his career, it's that he never aligns himself with a team unless he's certain he'll be part of a winning situation.
Jackson's smart enough to know that his legacy is already set in stone. He doesn't need to bolster it by taking on the difficult challenge of turning a loser into a winner.
So wherever Jackson ends up—assuming he does return to the league—it'll be in a place where the seeds of success have already been sown. All he'll have to do is help them grow.