15 worst Chicago Cubs free agent signings in franchise history

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3. Edwin Jackson - Four Years, $52 Million (2013)

When we look back at the Theo Epstein era of Chicago Cubs baseball, it will always end in fond memories of the 2016 World Series and the washing out of a 108-year championship drought. But we also know that not every move was a home run and few missed at the level of the Edwin Jackson signing.

Before we delve into a deep chasm of disappointment, your fun fact about Jackson: he's played for more MLB teams (14) than any other player in baseball history. Love him. Hate him. Still a fun fact.

The 2013 Cubs were pretty not great, finishing the year at 66-96. Jackson, for his part, managed to lose a league-worst 18 games - but as we all should be well aware by this point, wins and losses are hardly the best way to evaluate pitchers. His 4.98 ERA was certainly unsightly, but a a 3.79 painted a more optimistic picture of his work. Regardless, a WHIP north of 1.400 isn't going to get the job done.

Things got decidedly worse in 2014 for the right-hander. Jackson allowed more than 10 H/9, battled control issues all year long and saw his WHIP climb even higher (1.642). By season's end, he was demoted to the bullpen - and no one had much faith in him being any better in 2015.

After losing his spot in the rotation early in 2015, Jackson once again headed for relief duty and was markedly more effective (2.91 FIP in 23 appearances). Still, looking for a clean slate, the Cubs designated him for assignment in July and cut ties with him shortly thereafter, eating the rest of his deal in the move.