Chicago Cubs: Five players the team ‘should’ pursue this offseason

1. Edwin Jackson

I saved the best for last. The Cubs are currently without a “true ace.” Well, here he is. Edwin Jackson is without a doubt the greatest pitcher to ever be drafted by the Dodgers in the sixth round of the draft out of Shaw High School in Columbus, Georgia. That speaks for itself.

Edwin Jackson has basically played for every team in the league. The reason for this is because there is a constant and overwhelming demand for his talent. It’s time for the Cubs to be next on that list.

The obvious advantage here is that Jackson knows every team in the league, inside and out. He could relay all their strategies to the Cubs ahead of games. It would be just like when the St. Louis Cardinals hacked and stole information from the Houston Astros, only this wouldn’t be illegal.

The Cubs need Jackson’s pitching expertise if they wish to be legitimate contenders next season. Jackson’s 15-year career is filled to the brim with remarkable feats. An All-Star in 2009, a World Series champion in 2011, and one of the few pitchers in baseball history to throw a no-hitter, Jackson has done it all and then some.

Of all the players on this list, Jackson will be the most expensive. But the Cubs have assets. If Victor Caratini is ready to step into the starting catching role, Willson Contreras could make a good centerpiece in a package for Jackson.

Next: Cubs need Heyward to figure things out at the plate

There you have it, front office. Better get cracking. There is no wiggle room here. If there’s still space to make it happen, it might not be a bad idea to go after an outfielder as well. Jorge Soler is the first name that comes to mind. Here’s to seeing these new faces in 2018!