Phil Jackson Could Be Perfect Mentor for Ailing Knicks, but It Won't Be Easy

NEW YORK—Three months before he ambled away from the Los Angeles Lakers for good, Phil Jackson was already pondering his next endeavor.

UPDATE: Friday, March 14 at 5:02 p.m. ET

The New York Knicks are expected to announce the hiring of Phil Jackson at a press conference on Tuesday, March 18 (via Knicks PR):

--End of update--

It would not be in politics, despite his acute interest in the subject.

It would not be a speaking tour, a surely lucrative but empty pursuit.

It would not be in coaching. Jackson seemed certain of that much, too. His mind was willing, but his body was uncooperative. Several surgeries lay ahead.

One idea, broad and undefined, held the most appeal.

“I think mentoring is something that I’d be very comfortable doing,” Jackson told me over lunch in February 2011.

Mentor who? Coaches, preferably, though coaches can be famously headstrong, Jackson noted.

The seeds of a broader vision were evident, even then. Jackson wanted to share the wisdom he had accumulated over four decades in basketball. What form that might take, he wasn’t yet sure.

Now we know. Jackson, 68, is close to joining the New York Knicks as their top basketball executive, according to an NBA source. 

This is the ultimate evolution of Jackson’s mentoring impulse: to teach an entire franchise—indeed, the league’s most dysfunctional franchise—how to win. To impart all that he knows about team building, trust, strategy, training, preparation, work habits and, yes, Eastern philosophy. If any team needs a lesson in Zen, it’s the Knicks.

And no building needs a karmic cleansing more badly than Madison Square Garden, the world’s most toxic arena.

Tony Gutierrez/Associated Press

In Jackson, the Knicks are buying themselves a sheen of credibility, a stabilizing figure after 15 years of wild instability. They are also buying a new symbol of hope, something the Garden does almost annually.

Some skepticism is understandable.

Though Jackson’s credibility is engraved in those 11 shiny rings, he has never run a front office. Yet isn’t this the same path Pat Riley traveled, from coaching icon to exalted executive? Didn’t Larry Bird make a similar (and much quicker) leap from coach to team president?

The sharpest basketball minds find a way to channel their genius in whatever role they find. And Jackson is not seeking a traditional daily general manager job.

The role Jackson covets is best described as “philosopher-in-chief.” He wants to set the agenda, to establish a culture and a values system, to identify the type of players and coaches a team should pursue, the offensive and defensive philosophies it should adopt.

That could even extend to shaping the team’s training regimen and its use of analytics—an area that fascinates Jackson, and one he would surely seek to bolster. (The Knicks lag far behind many teams in this area.)

Contrary to speculation, it’s unlikely that Jackson would attempt to do the job from his beach house in Playa Del Rey, Calif. Those who know Jackson best say he would not take a job like this without relocating. And there is no doubting Jackson’s affection for New York—“a magical place to live,” he told me in 2011.

This much is also true: Jackson has no interest in getting cozy with agents, or poring over salary-cap minutiae or scouting college games. He will need a strong and experienced front office working with him. That might spell the end for Steve Mills, who was just hired as president and general manager last September. Mills is a savvy business executive, but he had never worked in basketball operations, and he has done nothing significant to date.

Indeed, Jackson could conceivably overhaul the entire front office. It’s hard to seem him coming out of retirement to be a distant figurehead, overseeing the same feckless crew of Garden loyalists and Creative Artists Agency cronies.

And it’s a safe bet that Jackson would not risk his reputation without getting strict assurances that he can work without interference from those same forces—and freedom from Dolan’s infamous media policies.

Donnie Walsh sought similar assurances before becoming team president in 2008. He resigned three years later, fed up with the incessant meddling by owner James L. Dolan and his advisers, including CAA (Creative Artists Agency) and the ubiquitous power broker William Wesley.

Since then, CAA has only dug its tentacles deeper. The agency represents Carmelo Anthony, J.R. Smith, coach Mike Woodson, assistant general manager Allan Houston and director of player personnel Mark Warkentien. Wesley played a role in Mills’ hiring last fall.

And it was CAA, according to sources, that persuaded Dolan to make the ill-fated trade for its client Andrea Bargnani—over the concerns of the Knicks’ front office.

“If (Jackson’s hiring) breaks the stranglehold of CAA, I want it to happen,” said an agent who does business with the Knicks. “I can’t see him in a million years working with them.”

Jackson, a fiercely independent soul who has no ties to CAA, seems like the right man to break that stranglehold. He will certainly look to hire his own people—that is, assuming Dolan is finally ready to grant full authority to his top basketball executive, and get out of the way.

Kathy Willens/Associated Press

And really, this is the key calculation for everyone: Has a decade of meddling and misery convinced Dolan that he’s been doing this the wrong way? That it’s time to try a different approach? Has he noticed that he is the only NBA owner whose fans are staging a protest next week?

If Dolan provides Jackson with the autonomy he needs, if Jackson proves as adept fostering a healthy office culture as he is at promoting a harmonious locker room, then the Knicks may yet have a ray of hope, and Dolan may yet find redemption.

It will be a fascinating culture clash: Dolan’s paranoid, iron-fisted autocracy vs. Jackson’s free-spirited individualism. Dolan is intolerant of dissent and known for profanely upbraiding anyone who challenges him. Jackson is candid, unfailingly outspoken and headstrong. No one tells him how to run his team—or when he can speak to the media. Dolan isn’t likely to be the first.

If this ends badly, as so many are predicting, it will only serve as fodder for another Jackson tell-all book. That alone should motivate Dolan to release his suffocating grip.

Three years ago, as Jackson picked over his lunch at a Boston hotel, I asked whether he had any sentimental pangs about what would be his final trip to Madison Square Garden as an NBA coach. No, he said. He’s not the sentimental type. I asked about a possible reunion with the Knicks, the team that drafted him in 1967. Jackson demurred there, too. A front-office job? “I can’t see why,” he said, dismissively.

So, what then?

“I think there’s going to be opportunities that lead me in directions, and I hope I have the distinction to know how to move inside of those,” Jackson said.

It was a perfectly Jacksonian response, sounding confounding and reasonable all at once. Sort of like deciding to work for the Knicks.

Howard Beck covers the NBA for Bleacher Report. Follow him on Twitter at @HowardBeck.