What keeps Adam Silver up at night

THE CONVERSATION NBA COMMISSIONER Adam Silver had with Bill Simmons last week in Boston was perhaps the most candid and personal of his tenure. It was a refreshing departure from standard public sessions, which are often filled with rose-colored and obfuscation-filled comments.

One month from his five-year anniversary in the job, Silver admitted that the NBA has some real challenges. He said the league has made some mistakes that have caused him to lose sleep. He hinted that he's even re-evaluating what he wants his identity as commissioner to be.

There's no crisis, per se. Anyone who runs an $8 billion worldwide operation is always going to be managing a full plate of problems. He was…