Executives at Caesars Entertainment Corp. know a few things about when to hold 'em and when to fold 'em. But when those gambles lead to a federal investigation into possible money laundering, as well as state-led investigations in both Massachusetts and Nevada, it seems that Caesars went all-in at the wrong time.

Caesars disclosed on Oct. 21 that tis being investigated by U.S. government for potential money laundering. A letter from the Treasury Department's Financial Crimes Enforcement Network, dated Oct. 11, told Caesars Palace owner Desert Palace Inc. that the government was investigating possible Bank Secrecy Act violations and weighing whether to take civil action.

As a result, Massachusetts investigators suggested denying a permit for a Caesars project in Boston. The company also ended a hotel licensing deal in Las Vegas ahead of any potential enforcement action. These legal problems have sent Caesars' bottom line tumbling —Caesars Entertainment Corp. stock is down 33 percent from its record close on Sept. 17.