Nick Swisher was mostly a headache for the Chicago White Sox organization.
Unlike the other two names on this list, Nick Swisher was not a free agent signing. But the move turned out so bad that the contract they took on looks completely unreasonable given the end result.
Jim Thome gets along with almost everyone but even he knew that Nick Swisher was going to be a problem from the first day he entered the locker room. Swisher entered the clubhouse acting like he had just taken an IV shot of coffee and was screaming like a banshee.
The White Sox were two years removed from the World Series. They were still looking to contend in 2008 so Kenny Williams swung a trade for Nick Swisher. Swisher was brought in with the hopes he could be their leadoff man. He was coming off a season where he drew 100 walks and had a .381 OBP. Swisher had hit 35 home runs in 2006 and 22 in 2007 so he provided some power as well.
The White Sox parted ways with Gio Gonzalez (who later emerged as a solid pitcher) and Ryan Sweeny (who went on to be an everyday player for the Oakland A’s) to acquire him. The White Sox still decided to take on the four years remaining in his contract that had an average salary of $5,350,000.
The move turned out to be a total flop. He batted .219 and his.OBP dipped to .332. By the end of May, he was hitting in the seventh and eighth spots in the lineup. On defense, he was a train wreck. He committed seven errors and was worth a -11 defensive runs saved in just 70 games.
Swisher also got benched for having a poor attitude. The White Sox traded assets for him with the intention of keeping him for four seasons. They couldn’t get rid of his contract fast enough, trading him to the Yankees weeks after the season was over. It was still $3,500,000 they will never get back.
What made the move even more frustrating was the fact that Swisher went on to become an All-Star the following season and won the World Series with the Yankees. Hopefully, the team is just a bit smarter going forward.