On July 29, 1970, the Cubs traded their top prospect, shortstop Roger Metzger (who went on to play a decade in Houston) to the Astros for a player that had just walked out on his team because they tried to give him a roommate on the road—Joe Pepitone.

Pepitone was a great glove man with power, but he also had one of the worst attitudes in Cubs history. The fans loved him though, because he was flamboyant, and showy, and everything else the Cubs had always lacked. He hung out at the Playboy club, he wore his hair long (and wore wigs), he wore his shirt open to show his hairy chest and gold chains, and he was the first player in baseball to bring a hair dryer into a clubhouse.

On his first day as a Cub he arrived in a limo. He was so deep in debt he owed the team half his salary before the year began. He bought a club on Division Street and called it “Joe Pepitone’s Thing.” He opened a hair salon and started selling Joe Pepitone wigs. He parked his Harley inside Durocher’s office so that kids wouldn’t bother him after the game. And while things were going well for the Cubs, Joe Pepitone was not a problem.

On the other hand, manager Leo Durocher—who recognized a young version of himself in Pepitone—knew it was just a matter of time. In his autobiography “Nice Guys Finish Last,” this is how he referred to him.

“If you’re thinking that Pepitone was sent to me in just retribution...I have to admit there were times that the thought crossed my mind.”

When things starting going bad, Pepitone was always in the middle of it. He had a real problem with authority figures and he incited some of his teammates to feel likewise. The relationship with Durocher soured, and became toxic.

It all blew up in 1972. He walked out on the team on May 2, 1972 and asked to be put on the voluntary retirement list. He was sick of baseball and wanted to concentrate on his nightclub, but as usual, the money sent him crawling back. Unfortunately for Pepitone, being placed on the list made him ineligible for sixty days. He returned the very first day he legally could, but he was rusty and just couldn’t hit anymore.

A year later the Cubs sent him packing, trading him to the Atlanta Braves.