Richard Sandomir of the New York Times breaks down Bill Simmons’ move to HBO. He notes that while he has been successful on multiple platforms, he has yet to conquer television as a personality.

Sandomir writes:

Simmons had a not-so-dandy stint as an analyst on ESPN’s N.B.A. pregame show, “NBA Countdown,” and was the host of “The Grantland Basketball Hour,” which was more “Wayne’s World” than big-time programming. His columnist’s voice did not translate well to the screen, with the medium’s time limits and craving for sound bites.

John A. Walsh, the former executive editor of ESPN who was associated closely with Simmons, said that Simmons was trying to fit his television work into a lot of other endeavors.

“What Bill was attracted to was launching Grantland,” Walsh said, “and if you’re launching Grantland and writing a column and doing podcasts, I don’t know how much more time is left in the day.”

Simmons, who was said to be earning $5 million annually from ESPN, has long been considered one of the most original voices in sports journalism and a magnet for younger fans. David Hill, a former chairman of Fox Sports, said in an email that Simmons stood out from “an ever-crowded field of nonentities (the perennial talking head).”

Hill added, “Mr. Simmons has a voice and is a personality,” and said: “Personalities work! Look at what John Oliver has done for HBO — getting headlines within minutes.”

I like the potential for Simmons at HBO. Obviously, the network needs to come up with the right format for him.