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Fun speculation: Toronto may make run at Phil Jackson for front office

Apr 26, 2013, 5:22 PM EST

Former Los Angeles Lakers head coach Jackson speaks during a ceremony to retire jersey #34 in honor of former Los Angeles Lakers player O'Neal during their NBA basketball game against the Dallas Mavericks in Los Angeles Reuters

If you like some speculation and to connect the dots, we have a story for you: A move that got notice on the sports business pages could be the first step in a series of moves that lead to front page headlines:

Phil Jackson running the Toronto Raptors.

We’re a long, long way from that. But Marc Stein and Ramona Shelburne started to connect the dots in an ESPN.com story and we’ll follow along because it’s too fun not to.

It all starts with the fact Tim Leiweke was just hired as the new president and CEO of Maple Leaf Sports and Entertainment, the company that owns the Raptors (and Maple Leafs of the NHL, as well as other sports entities). Most of the nation just said “who?” but people in Los Angeles know Leiweke as the former CEO of AEG who was a force in Los Angeles sports — he got Staples Center built, he got AEG to buy a stake in the Lakers (estimated at 30 percent), he brought David Beckham to the Galaxy of the MLS, and he got plans for a downtown NFL arena in L.A. farther than any other man has. He’s a man who likes to make bold, big moves.

From there we let Stein and Shelburne connect the dots.

Sources told ESPN.com this week that the Raptors have interest in talking with Jackson about the Pat Riley-style role he craves in charge of a team’s basketball operations. ESPN.com reported last week that Jackson, after nearly two seasons in retirement, is itching to return to the NBA next season, preferably in a role similar to Riley’s in Miami that allows him to oversee both the basketball department and the coaching staff or perhaps as a high-level consultant such as Jerry West in Golden State.

Leiweke is a major player in the sports industry, and Jackson is all-too-familiar with his work in Los Angeles, where he helped get the Staples Center.

Leiweke can get Jackson to pick up the phone (and he’s taking meetings with everyone who calls anyway, he wants back in). While reports had been that current Raptors GM Bryan Colangelo will keep his job — and with him coach Dwane Casey stays in place — you’d have to explore the Jackson idea if you’re the Raptors, don’t you?

It’s easy to think of ways this falls apart. Jackson thinks it over and decides he doesn’t want to move to Toronto for the winter. The Raptors are not willing to meet Jackson’s financial demands, which you know will be steep. Jackson has options — he said he’s had exploratory talks with a few teams and the buzz is one of those is Seattle should they buy the Kings — and he may choose another location to jump back in the league.

But stranger things have happened. The biggest problem with the Raptors in recent years seems to be a lack of a plan — they have assembled some nice pieces but there is no overarching design. Jackson would be the big-picture kind of guy they need. Whether he has the skills to execute that in a front office role remains to be seen. Plus wherever Jackson lands there will be a clamor for him to return to the bench, something he is not eager to do.

But it’s out there. And it’s fun to talk about even if it is unlikely.

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