50 Cent

Qualifications: Consummate brand builder, not afraid to step out of his comfort zone, and also the "React" video with Onyx.

If he can sell healthy (sort of) drinks to the city, he can certainly help devise new ways to sell hockey. He's not got any explicit art related enterprise, but given his competitive spirit there is little question he'd rise to the occasion and attempt to best Jay-Z's efforts with the Nets. We like the idea of cross-sport battle.