Chicago Cubs: Did last winter cost the team a chance at success?

Chicago Cubs: Trying to ‘buy low’ not going so well

The last couple of years, the Cubs have tried to find an undervalued pitcher to be their fifth starter. In 2017, Brett Anderson and Mike Montgomery competed for the job in spring training. This year, the Cubs had several options. Montgomery publicly stated his desire to be a starter. There were some rumors that the Cubs might be interested in Miles Mikolas. Jhoulys Chacin had some interesting upside. All three of them ended up pitching well.

But the Cubs went with Tyler Chatwood. There was a lot to like about his numbers away from Coors Field. Reports noted a lot of nasty movement on his pitches. So Chatwood could have turned out to be a free agent steal.

Instead, he wound up experiencing historic levels of wildness. Clearly he did not work out in 2018. The question now is how do the Cubs pick up the pieces and move on from here. They can’t count on Chatwood to hold a spot in the rotation.

Should they even allow him to hold a roster spot on Opening Day? Do they end up dumping him? If so, the Cubs will have to pay Chatwood $25.5 million over the next two years not to pitch for them. Could they find a team to take a chunk of his contract?

Clearly in 2018 Montgomery, Mikolas or Chacin would have been a better fifth starter. However, if Montgomery began the season in the rotation, who would have filled in when Darvish was injured?