He knows the power of names and reputation.
With TFC, he knew he was the name... his reputation of bringing in Beckham and making the Galaxy the biggest name in MLS is that clout. He then gets Dafoe and Bradley and even brings back Derosario... instant credibility brought back to the franchise.
With the Raps, he hires the GM of the year, and he hires Drake as the embassador. (which also helped lure in Dafoe) We may think of Drake as just the degrassi kid, but he's got clout in the ipods of bball players.
The one thing he hasn't done is made that splash for the leafs. As he said in the interview, he thought with last years success that they didn't really need it, but with this swoon he is gonna get that name that he's looking for. With the cap, he can't really do it with roster players.. (although I could see him not giving a crap about the money in a buy out and dropping Clarkson.
I really think he is gonna go for Gretzky and Nicholson. As President and President of hockey operations or whatever. Lieweke knows the power of names and there are no bigger names in Canadian hockey than Gretz and Nicholson.