The clock is ticking on the Masahiro Tanaka derby, meaning we’re likely near another wave of big free-agent signings just in time for pitchers and catchers to report for spring training. Hard to imagine, but in about a month, the familiar sounds of rawhide smacking the leather in the bullpen will return to Arizona and Florida.

It’s clear that baseball contracts are rising after a year when the league pulled in a record $8 billion in revenue in 2013, according to Maury Brown of Forbes. New national and local TV deals are also kicking in around the league, meaning players are reaping the benefits at the negotiating table.

With such big contracts come big risks, and there certainly have been some moves made this offseason that look poised for failure. Here’s a look at 15 signings and/or trades executed this winter that are most likely to backfire on their respective clubs.

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