The once-sprawling criminal case against Dewey & LeBoeuf’s top executives shrank once again on Friday, dealing a fresh blow to New York prosecutors who had accused Dewey’s leaders of duping lenders about the firm’s precarious finances.

A Manhattan judge dismissed 15 grand larceny charges against former Dewey & LeBoeuf executive director Stephen DiCarmine and former firm CFO Joel Sanders, who remained in the case after Dewey chairman Steven Davis reached a deferred prosecution agreement in January. Manhattan DA Cyrus Vance had initially charged the trio with more than 100 criminal charges, raising the specter of decades in prison for the top executives of the largest law firm ever to file for bankruptcy.

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