I'll tell you a bad career move: Rod Evans, Deep Purple's original lead singer.
He recorded 3 albums with them, then faded from sight.
In the late 70s, he resurfaced in LA with a band that called itself 'Deep Purple'. The original bassist, who was ejected the same time as him, had more sense than to join this enterprise. There were sellout concerts, but the band was fairly crap, apparently, vast refunds happened, and eventually DP's management put notices in the local and trade papers saying the better known members of the band would not perform. With all the legal pressure, the band folded.
And if that wasn't bad enough, he had to sign an agreement forgoing his royalties to the DP albums he sang on. This would have brought him in a tidy earner over the years since they were recorded, and I noticed that DP's version of 'Hush' that he sang on, is being used in ads for one of the Woodstock films, which will also be an earner. But not for him.
So with one bad decision, he neutered any kind of comeback and cut off a money stream.
