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4) Dave Roberts-5 years, $1.3 million
The Astros gave Dave Roberts five years in hopes he would fill a super utility role for them moving forward. Very rarely do teams find a player than can play both catcher and shortstop.
Sadly for Houston, they realized Roberts couldn't play any of the utility spots very well. In 27 games as an Astro, Roberts hit .241 with a .623 OPS. Though the season was shortened by a strike, Roberts was very poor in the time he was able to set foot on the field.
Houston traded Roberts the following spring training, though they still had to pay him. Talk about a worst case scenario.