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.

According to regulators, disciplinary action should not be unexpected. “If federal laws have been violated, that could very well lead to disciplinary action based upon Nevada gaming laws,” A.G. Burnett, chairman of the Nevada Gaming Control Board, said in an e-mail to Bloomberg. Caesars said in a regulatory filing that it is cooperating with both the Treasury Department and federal and state investigators.

This investigation into the largest owner of U.S. casinos comes on the heels of a $47 million penalty for fellow Vegas mainstay the Las Vegas Sands after the Treasury Department raised similar money laundering charges. The government ordered the Sands to review its anti-money laundering policies and file consistent reports with the government that it is abiding by federal law.

Because of the large amounts of money flowing through casinos, the largest are regulated similarly to financial institutions and are subject to Financial Crimes Enforcement Network regulation. That organization was expected to draft new anti-money laundering rules after the Sands probe, and this Caesars investigation makes that even more likely.