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

Chicago Cubs: Team opted to go with what they knew

Last offseason was more about what they didn’t do than what they did when it came to position players. The Cubs did not re-sign Jon Jay. They did not trade for Manny Machado. Nor did they trade away Addison Russell or any of their other young bats. The Cubs did not sign any big name free agent hitters. However, they did closely follow Lorenzo Cain‘s free agency.

There was a lot of talk about the possibility of the Cubs trading for Machado. At the time a lot of the debate came down to is one year of Machado worth multiple years of inexpensive team control of players such as Russell. If the Cubs had traded for Machado that would have given them the inside track to either sign him to an extension or re-sign him as a free agent now.

What was the right thing to do about Machado is still not clear. However, I am now wondering if the Cubs had enough of a hint about Russell’s off-the-field issues last off season that they should have been working to trade him away. Now, Russell still has to serve 29 games of his 40-game suspension to open 2019.

If they had traded the young infielder away then, the Cubs wouldn’t be faced with the messy decisions they have to deal with now. If not for Machado, maybe they could have traded him for pitching or to restock their depleted farm system. The Pirates didn’t get much for Gerrit Cole.

As for Cain, I think there were two possibilities there. One, the front office was closely monitoring his situation in case his contract situation turned into Dexter Fowler‘s contract from 2016. Two, the front office was going to sign Cain if they traded away a young outfielder or two.

With Epstein’s comments about valuing production over talent perhaps Andrew McCutchen is the Cain of 2018. Of course there is another free agent outfielder you may have heard about.

Last year’s free agents did not help the Cubs in 2018. However, with the exception of Gimenez, all of those free agents signed multi-year contracts and will be back next season. Imagine how much better the Cubs could be in 2019 if those free agents play the way we thought they would when they signed their contracts.

With 2018 being one of the best free agent classes in recent history, the Cubs have a chance to significantly improve upon an already playoff-worthy roster. Hopefully, the front office has learned some lessons from the last off season.