Chicago Cubs fans are still cringing at Edwin Jackson’s contract

The Chicago Cubs have made some big transactions during the Theo Epstein era but one will haunt them despite winning a World Series title several years later.

It is normal for general managers to drop the ball when it comes to investing in talent. Nobody is perfect. Two years after signing with the Chicago Cubs, Theo Epstein made a bold decision by signing right-hander Edwin Jackson to a four-year, $52 million contract.

Keep in mind, he had already gone out and acquired first baseman Anthony Rizzo from the San Diego Padres in 2012. Of course, that amounted to a trade that cemented a blueprint designed for success following his remarkable and historic tenure with the Boston Red Sox.

When the deal was finalized, Jackson was inserted into a starting rotation that included Jeff Samardzija, Travis Wood, Carlos Villaneuva and Matt Garza.

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Garza was acquired by the Cubs from Tampa Bay on January 7, 2011, in a package that involved Sam Fuld, Brandon Guyer, Robinson Chirinos, Hak-Ju Lee, and Chris Archer. A month prior, former Rays first baseman Carlos Pena inked a one-year, $10 million contract.

Tampa won both transactions as Archer emerged as a star in Joe Maddon‘s rotation and Pena returning to the Rays organization following the 2011 campaign. At least Carlos provided the Cubs with a little something before he was allowed to walk.

As for Jackson? Not so much. In his brief stay with the Cubs, Edwin earned at least $600k of his deal in July 2013. Throughout 34 1/3 innings (five starts), Jackson yielded seven earned runs on 24 hits (one home run) while striking out 22 batters along the way.

His record of 3-1 was backed with an earned run average of 1.83 before starting August with a seven-run, 10 hit outing. Eventually, he’d lose a rotation showdown with Wood, finding himself working from the bullpen yet again. Probably where he should have started in the first place as 32 of his 47 relief appearances were scoreless outings before being designated for assignment.

The decision to cut him loose forced the Cubs to eat a healthy chunk of his contract. Around $13 million worth, to be exact. To this day, fans are wondering what Epstein was thinking when he approached Jackson’s camp with an offer that large.

Sure, Theo has made a ton of excellent moves over the years but this one still leaves a bad taste in your mouth. Jackson, at best, posted a 3.62 ERA as a starter with 33 games under his belt in a Tigers uniform.

That year, he struck out a then career-high 161 batters before eclipsing that total with 181 between Arizona and the White Sox in 2011. With that said, Jackson’s strikeout total within four years could have been what Epstein was drooling over.

You could say the same for Jason Heyward and his Gold Glove in right field. Epstein signed Heyward to a massive eight-year, $184 million contract — similar to Boston’s deal with Carl Crawford in December 2010.

Like Jackson, Crawford failed to live up to expectations. Only he played out six of seven years before he was traded to the Dodgers. Luckily for Theo, he is known for ending curses.