Chicago Cubs: Theo Epstein’s made few mistakes in Chicago

 Cubs sign Jackson to four-year, $52 million deal

This one falls as one of the more difficult ones to swallow in the Epstein era. If you look at the Baseball-Reference page of Edwin Jackson, it’s a long list of teams and jersey numbers. Jackson had never shown enough to convince any other team to sign him to a long-term deal. But the Cubs turned out to be the ones to fall for it.

The thought was that Jackson could be an innings-eater, helping to anchor the staff. Jackson had been around or over 200 innings pitched each year since 2008, so that plan made sense. The team also thought that as they improved, Jackson would be there to assume his place near the top of the rotation as they “turned the corner”.  He turned out to be none of those things, except very, very costly.

In his first two seasons, Jackson went 14-33 with a 5.58 ERA. I see no reason to go into deeper metrics because none of those are any better. Jackson was horrible. But unlike Stewart, the Cubs didn’t seem to know what to do with him. And unfortunately, losing 33 games in two seasons doesn’t attract a lot of suitors for a trade.

In 2015, Jackson was moved to the bullpen and seemed to have gotten back on track. In 31 innings pitched he posted a 3.19 ERA with the Cubs. But that July Epstein finally pulled the plug on the E-Jax experiment, releasing him. The Braves picked him up–on the Cubs tab, mind you–and pitched well for them the rest of that season. He’s had a stint with the Marlins and the Padres but is currently a free agent this winter.