The offseason is full of acquisitions that end up making or breaking a team’s short- and long-term chances. This winter has proven no different, and Jim Bowden of ESPN has produced his list of five transactions that are likely to backfire, including Angel Pagan, Nick Swisher, Jeremy Guthrie, Joe Blanton and Marco Scutaro.

While San Francisco Giants general manager Brian Sabean is the owner of two World Series championships in the last three years, Bowden says he doesn’t have a perfect report card by any means; see Barry Zito and Aaron Rowand. Bowden is more worried about the length of Pagan’s contract, as he hasn’t proven a consistent player at the major league level. He also doesn’t like the length of the deal signed by the 37-year-old Scutaro.

Bowden believes Swisher’s deal with the Indians will work out for the first few seasons for Cleveland. However, he doesn’t like committing $56 million to a declining player that doesn’t’ "profile as a legitimate 3-4-5 hitter."

Guthrie turned his season around after the Kansas City Royals acquired him from the Colorado Rockies. However, Bowden thinks his three-year, $25 million agreement could be one of the worst signings by the club since Gil Meche.

Blanton was uninspiring in the National League of late, leading Bowden to say that his ERA will be "well over 5.00" in the junior circuit. He says the Los Angeles Angels’ two-year commitment will end up being a mistake.