Jackson's first order of business in the Big Apple may well be his toughest: getting in good with team owner (and notorious meddler) James Dolan.
The heir to the Cablevision empire is certainly a fan of Phil's. According to Marc Berman of the New York Post, Dolan had tried twice before to lure Jackson back to New York—in 1999, when Jackson declined to unseat Jeff Van Gundy while the latter was still on the job, and in 2005, when Isiah Thomas was at the controls, just before Phil resumed his place on the sideline in L.A.
For Jackson to succeed with the Knicks, he'll need to keep Dolan at arm's length from making any important basketball decisions. That's (much, much) easier said than done, if the abbreviated tenures of Donnie Walsh and Glen Grunwald are any indication. Dolan reportedly went against Walsh's wishes in engineering the Carmelo Anthony trade in 2011 and deposed Grunwald of his duties mere days before the start of training camp, even though Grunwald had put together last year's 54-win team.
Jackson will have to wade through some rather murky political waters to make sure his own stint doesn't end the same way. If anything, it would behoove Jackson to follow Thomas' example—not in terms of basketball decisions, but rather in terms of ingratiation. As Yahoo Sports' Adrian Wojnarowski noted, Zeke seized near autonomy in the front office from Dolan by buddying up to the billionaire.
Jackson, though, has never been one to play nice with his superiors. He clashed with Jerry Krause in Chicago and Jerry West in L.A., even though both had proven themselves to be front-office gurus.
If anything, a Jackson-Dolan relationship could resemble the fractious one between Phil and Lakers executive Jim Buss. Like Buss, Dolan is the product of nepotism. His father, Charles Dolan, founded Cablevision, which acquired Madison Square Garden and its sports properties, including the Knicks, in the mid-1990s. The elder Dolan put James in charge of MSG in 1999.
Unlike Buss, Dolan doesn't have a championship pedigree on which to lean. Say what you will about Buss, but the Lakers won back-to-back titles with him playing a prominent part in the team's brain trust.
Dolan has no such successes on his resume, nor would he likely concede that he should hand over control of the team's operations to someone who does. Jackson's own enormous ego would probably make it difficult for him to stoop so low as to stroke Dolan's ego to any extent, even if only for the sake of appearances.
But if Jackson wants his first foray into NBA management to be worthwhile, he'll have to go against what appears to be his nature and "kiss up" to his boss as a demeaning means to a greater end.