Heading into the winter of 2012, the Cubs’ biggest free agency target was right handed starting pitcher Anibal Sanchez, offering him a 5 year, $75 million deal. Unfortunately for the Cubs and their fans, Sanchez made it clear that he wanted to stay with the Detroit Tigers, the team he was traded to the previous summer, and gave the Tigers the opportunity to match or beat any offer he received from other teams. When the Tigers offered Sanchez a 5 year, $80 million deal, the Cubs moved on to plan B: Edwin Jackson, on a 4 year, $52 million contract.

While no one ever thought Jackson was as good as Sanchez, evidenced by the nearly $30 million difference between their contracts, Jackson had been a solid mid-rotation starter who could eat innings from 2009 to 2012. Yet while Sanchez found the next gear in his career since the start of the 2013 season,  progressing from a solid 2/3 to an ace caliber pitcher in 2013, Jackson took several steps back. While he’s eaten up innings, he’s done it at well below replacement value according the Baseball-Reference’s WAR.

There was an argument last season that it was just bad luck or random variation. His FIP and xFIP have been better than his ERA as a Cub (4.98 ERA, 3.79 FIP, 3.86 xFIP in 2013; 5.64 ERA, 4.26 FIP, 4.04 xFIP in 2014) and his strikeout and walk rates were close to his more successful stretch from 2009-2012, particularly last season. But we’re nearly 300 innings in, he has not been able to get consistent results (except when they’re consistently bad), and nearly 27% of batted balls against him in 2014 have been line drives (league average is 20%), leading credence to the argument that he’s being squared up by opposing hitters this season.

The real question, with nearly two and a half years and approximately $27 million left on Jackson’s deal and the Cubs likely looking to be more competitive next season, what can the Cubs do with Jackson?

The all the stars aligning answer is some fringe contender thinking they can fix what ails Jackson and offering to take a fair amount of the money off the Cubs hands for some lottery ticket prospect.  But is there a team that desperate, or a general manager that dumb with the Phillies being terrible? Probably not. The best target may actually be the Yankees, who just need arms to throw innings with all the injuries they’ve dealt with, and are always capable of adding payroll, but I’d be surprised if Cashman would take on a struggling 30 year old starter with a contract that long this month.

Should Jackson not be tradeable, as presumed, the Cubs really have no choice but to keep pitching Edwin Jackson for the remainder of 2014 to see if Jackson can turn it around. If he can’t? Can the Cubs really go into 2015 planning on Edwin Jackson throwing 180 innings or more? I don’t think so. It would mean admitting an expensive mistake, but not as expensive as continuing to throw Jackson as is out there every fifth game, particularly considering the Cubs’ ability to find solid mid-rotation arms on short term deals. The next two and a half months, though, are going to be very important for the future of Edwin Jackson’s career, and the construction of the 2015 starting rotation.

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Noah Eisner is a Chicago attorney living in the western suburbs with his wife and son (and impending daughter). When he isn’t practicing law or entertaining a toddler, Noah follows Cubs baseball with a focus on the farm system and sabermetric analysis. His Cubs-related ramblings can be followed on Twitter @Noah_Eisner.