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They Should Have Passed

The recent announcement that Edwin Jackson was DFAed finally ends the long saga of undoubtedly Theo Epstein and Jed Hoyer’s worst acquisition for the Cubs. Jackson, signed to a 4-year/$52 million contract prior to the 2013 season, struggled mightily in 2013 and 2014 before being demoted to the bullpen. Overall, he finished with a 5.37 ERA in 347 innings with the Cubs. Yet Jackson isn’t the only player the front office should have passed on. Below I review the top “misses” since Epstein/Hoyer took over in late October 2011. I've listed them in chronological order rather than ranking them: feel free to weigh in on which you think is the worst or if there are any clunkers that I missed (I've tried to purge some recent players from memory, so omissions are possible).