Nine years ago, Major League Baseball owners and executives privately wrestled with a difficult question: Should they allow Jim Crane to buy the Houston Astros?

The Texas businessman had offered $680 million to purchase the team, a sum that would mark the second-highest price ever for a baseball franchise at the time. But behind closed doors, owners and executives, including then-commissioner Bud Selig, were concerned about Crane’s business history, people familiar with the matter said.

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