In October 2005, Bob Iger was just a few months into his new gig as CEO of the Walt Disney Company when he announced a deal that would stun the entertainment industry. Standing next to Steve Jobs on a stage in Cupertino, Iger said that Disney would begin selling digital downloads of a handful of ABC and Disney Channel shows via Apple’s fledgling iTunes Store, including episodes that had premiered on TV just hours before. It was the first time a major Hollywood studio had agreed to (legally) let consumers bypass the broadcast and cable ecosystem to watch current seasons of shows as they ran on TV.

Exactly 20 years later, and likely just weeks away from announcing his (second) successor, Iger is once again trying to play trailblazer. As my colleague Eric Vilas-Boas outlined today , Iger

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