MLB Contracts: The worst contract on every team

BALTIMORE, MD - MAY 29: Chris Davis #19 of the Baltimore Orioles reacts after striking out looking for the third out of the first inning against the Washington Nationals at Oriole Park at Camden Yards on May 29, 2018 in Baltimore, Maryland. (Photo by Rob Carr/Getty Images)
BALTIMORE, MD - MAY 29: Chris Davis #19 of the Baltimore Orioles reacts after striking out looking for the third out of the first inning against the Washington Nationals at Oriole Park at Camden Yards on May 29, 2018 in Baltimore, Maryland. (Photo by Rob Carr/Getty Images) /
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CHICAGO, IL – JULY 07: Tyler Chatwwood #21 of the Chicago Cubs scratches his head while he walks in the dugout after the first inning of their game against the Cincinnati Reds at Wrigley Field on July 7, 2018 in Chicago, Illinois. (Photo by Jon Durr/Getty Images) /

6. Chicago Cubs

Tyler Chatwood, 3 years, $38 million, 2018-20. RMG

When assessing bad Cub contracts, the default option is Jason Heyward’s eight-year, $184 million deal. But two things mitigate against condemning that deal. The first is the fact that Heyward actually helped the Cubs win the franchise’s World Series in 108 seasons. The second is that while he hasn’t justified the amount he’s being paid, he hasn’t been a true bust.

Chatwood’s deal, signed prior to the 2018 season, carries with it both of those problems. Signed as a rotation starter, he won just four games in just 20 starts before being benched for incompetence. In only 104 innings, Chatwood walked a league-leading 95 batters, eventually necessitating the trade that brought in Cole Hamels.

Once Hamels arrived at the trade deadline, Chatwood became Chicago’s invisible man. He made just five appearances, only one of them a start, and pitched just nine and two-thirds innings. In fact the case could easily be made that Chatwood’s season-long failure to perform cost Chicago the chance to compete for a World Series return in 2018. Remember, the Cubs only lost the NL Central in a playoff following a second-half collapse that coincided with Chatwood’s functional disappearance.

The question facing Chicago is what happens now? Chatwood is not injured, so he’ll return to spring training as a potential rotation candidate. But that status, obviously, will hinge on his ability to demonstrate that he has fixed his pitching radar.

If he doesn’t, then what? The combination of his contract and performance render him untradeable, leaving the Cubs with three options. They could ship him to Iowa, making him the most expensive minor leaguer in history and hoping he improves there. They could release him and write off the $25.5 million he is still owed. Or they can keep him and essentially operate with a roster of 24.