3) Woody Williams-2 years, $12.5 million
The Astros committed $12.5 million to Woody Williams in 2007 hoping he would replace names like Roger Clemens and Andy Pettite in the rotation. Simply put, he didn't. Williams last only one of the two years on the deal, with the 40-year-old posting a 5.27 ERA and a 1.43 WHIP.
After Williams posted an 11.32 ERA in spring training in his second year in Houston, the Astros gave him his release, still on the hook for $6.25 million.
The Astros had absolutely no business committing that money to a 40-year-old with a 4-plus ERA for his career. The signing was one of the biggest misses in franchise history.