Dolan is defined by his love of nostalgia and star power. Phil fills both thirsts.
Phil very much fits the old Dolan logic of making splashy moves to satisfy the public (or what that seems to be in Dolan's mind). If Dolan were really interested in strategically overhauling management to compete with other modernized, statisically savvy, cap-savvy GMs, you'd try to put together your own money ball team and give them five years to prove their plan.
But the reason Dolan never did that is he trusts no one really. He's an incompetent basketball mind himself, but he's the boss and the only thing Dolan respects are personalities that can impress, awe or subjugate him. Dolan doesn't give a chit about expertise, lineage, background or competency. He is a starphucker. Always has been and always will be.
Phil satisfies Dolan's lust for showbiz moves and Dolan met his match psychologically in Jackson. In order to land the biggest hoops celebrity of the past 20 years outside of Jordan, Dolan had to make concessions and Phil knows how to play the psyche of a guy like Dolan. So Dolan landed his Big Kahuna, the kind he will step aside for psychologically.
None of this means Phil won't do good things. But it does mean Dolan's motivation for hiring Phil is pretty the same as it has always been. And Dolan probably does not want to deal with daily operations like Phil said, but Dolan's inability to assemble a management team and not meddle is well known.
All Dolan has ever shown is a thirst for the grand gesture. Open your pocketbook, unload your assets, whatever it takes to sign whomever you're coveting at the moment. Melo was the first real star he ever landed. The rest were expired former stars like Steve Francis or Larry Hughes.
Phil is just another grand gesture. This was the only way Dolan knows how to step aside. Whether he stays hand-off we don't know. But if he messes with Phil, I'd never be surprised if Jackson flips him off and walks. Stranger things have happened and Dolan is strange.