10 Worst Contracts in Boston Red Sox History

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10 Worst Contracts in Boston Red Sox History
Jared Wickerham/Getty Images
Carl Crawford is just one in a long line of terrible contracts the Sox have handed out.

The Boston Red Sox have begun to fill out their roster for the 2013 season and beyond. This has taken place amid pledges by GM Ben Cherington that the team will be spending freely this offseason, contrary to the commonly held belief that the Sox would be acting conservatively in the wake of last August’s payroll purge.

The team has quite a number of needs going into the offseason, with pitching chief among them. The Sox have a bad history with free agent signings in the pitching department, with many of the biggest busts in franchise history coming from acquiring these would-be aces.

This is not to sell them short on other areas where they have come up woefully short. Theo Epstein, in particular, made a habit of bringing in players who simply did not produce in a Sox uniform.

He certainly is not the only one guilty of handing out terrible contracts, though. Here’s a look at the 10 worst contracts the Sox have committed to:

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