Theo Epstein, the architect and GM of two World Championships, has been a master at his craft.
He has built the Boston Red Sox through the farm system and some of the gutsiest trades in Sox history.
But, he has shown flaws under his reign and the most glaring has been his free agent signings.
Epstein has had gems like David Ortiz, Mike Timlin and Bill Mueller.
Yet, he's whiffed on most of his signings.
Here is a look at the Top 10 worst free agent signings under his helm.