Throw in a roster he once described as "clumsy," a possibly departing superstar and a destructively meddlesome owner in need of a scapegoat, and you're left with the greatest challenge of Jackson's legendary career.
Leave it to the Knicks to dish out $60 million to clean the mess they created—and have it seem like a door-busting rate.
"The Knicks are low on draft picks and assets, long on bad contracts and bad knees," wrote Adrian Wojnarowski of Yahoo Sports. "For even the most elite of front-office executives, this is a challenging job – never mind a 68-year-old who'll find little of the adulation of championship-level coaching, and far more the criticism and second-guessing that comes with a rebuild."
Jackson's name is synonymous with championship bliss. He picked up a pair of rings during his playing career and added 11 more to his collection during his 20 years as an NBA head coach.
Notably absent from his resume, though, is any time spent in the front office. He's never before held a position like the one he'll receive a $12 million annual salary for filling, the impossible gig tarnished by a troubling past and tumultuous present.
This franchise has been trapped in a decade-plus search for relevance. The Knicks have just four playoff appearances and a single series victory to show for the last 12 seasons.
The organization's desire for success sits surprisingly low on Jackson's concern meter, though. His first—and perhaps most important—hurdle is freeing himself from the suffocating clinch of Knicks owner James Dolan.
Cross that bridge, and Jackson will have already fared better than many of the failed executives before him.
"Lots of highly regarded basketball men have come aboard with the understanding that Dolan would let them do their job — hello Larry Brown, Donnie Walsh and the rest of you basketball lifers — only to find their authority undermined," The Record's Steve Popper noted.
"I don’t think it’s so much a question of whether Phil can do the job as much as it is Jim being willing to say ‘my way hasn’t worked, so I’m going to let Phil do it his way,’" an NBA executive told Frank Isola of the New York Daily News.
History paints this possibility as D.B.A.—dead before arrival. Dolan kept his paws off at the start of Donnie Walsh's tenure, but once he saw splash potential (in the form of a disgruntled Carmelo Anthony), he made his move.
That makes it difficult (if not outright impossible) to take Dolan at his word when the owner says he'll grant Jackson full rule of the roost, via CBS Sports' Ken Berger:
The Dolan dynamic could plague Jackson's tenure from the start, but it's far from being the only potential pitfall the new Knicks president will encounter.
The roster is a jumbled mix of square pegs, round holes and medical red flags. With nothing more than a participation grade required for a postseason spot, the Knicks are still sitting four games outside of the playoff picture—after winning six in a row.
It's bad now and won't get any better next season. Given New York's salary commitments for 2014-15, you'd think this team was preparing for a championship push, not building a small collection of draft lottery balls that actually belongs to someone else.
|New York's Frightening Finances for 2014-15|
|Tim Hardaway Jr.||$1,250,640|
It should be noted that both Amar'e Stoudemire and Andrea Bargnani can opt out of their contracts this summer. But they'd have to be crazy—or have Andrei Kirilenko's agent—to walk away from that kind of money and think they'd find anything remotely close elsewhere.
Assuming these eight players are all around for the start of next season, the Knicks will already have more than $64 million on the books. For reference, the salary cap was set at $58.679 million for 2013-14.
Perhaps you've noticed a notable name missing from the eight listed above. Anthony, far and away the best player on the roster, may not be a part of it come next season. He's admitted he wants to play the free-agent game and appears undecided about how much, if at all, Jackson's arrival will impact his decision.
"Jackson’s first job will be to convince Anthony that it’s worth sticking around, that he will be able to build a championship team in New York before Melo’s prime is up," USA Today's Sean Highkin wrote. "It won’t be easy."
Nothing about this will be easy. Not even for the man with more championship rings than fingers to wear them.
He's forced to build without any raw construction materials at his disposal.
Salary relief won't arrive until 2015. New York has already shipped out its first-round pick in the 2014 and 2016 drafts. His star player and employer both need to see a splash, conveniently ignoring the fact that this pool is empty.
Jackson gives this franchise a respected, recognizable face to help with its recruitment of top free agents, but he doesn't have the funds to actually pay those players for their elite-level services.
He has balanced superstar egos, bonded fractured locker rooms and always found a path to the podium in the end. Maybe he's past the point of second guessing, even if this is the first time a front-office question has been raised.
Then again, he's never dealt with a beast like Dolan's Knicks before.