Worst Deals Ever?

[Jayworld]

As a longtime Rangers fan, we've had more than our share of awful trades, including the following:

April 1, 1982: Texas trades right-handers Ron Darling and Walt Terrell to the New York Mets for outfielder Lee Mazzilli.

December 8, 1983: Jim Sundberg was traded by the Rangers to the Milwaukee Brewers for Ned Yost and Dan Scarpetta (this trade almost killed my grandfather...he hated Doug Rader for the rest of his tenure as manager)

July 29, 1989 – The Texas Rangers trade pitcher Wilson Alvarez, outfielder Sammy Sosa and infielder Scott Fletcher to the Chicago White Sox for outfielder Harold Baines and infielder Fred Manrique.

[paul]

As a Red Sox fan, I'll never get over the signing of Matt Young in 1991. Going into the '91 season, he had the worst won loss percentage of any pitcher in history with as many decisions as he had. Every team that had previously signed him paid him a few hundred thousand a year. The Red Sox decided to pay him $2.3 Million per year for I don't remember how many years. They may still be paying him. He rewarded them with a typical performance -- 3 wins and 11 losses and an era of about 5 over two years. The guy sucked before they signed him, they gave him a huge raise, and he sucked just as bad after they signed him. Just a horrible, horrible move.