At one of Playboy's first big bashes after going private in 2011, much seemed as usual for a brand that has embodied American hedonism for nearly 60 years. Bunnies and Playmates sashayed beneath black crystal chandeliers in The Palms Casino's Playboy Club in Las Vegas, while men in suits hit the dance floor.

One of them was Scott Flanders, 55 years old, Playboy Enterprises Inc.'s first CEO outside the family of founder Hugh Hefner. But the appearance of the uninterrupted good life was largely an illusion. Mr. Flanders was...