The Chicago Cubs (Diamond) Dynasty that could have been

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Kyle Schwarber

Position: Left-Handed DH

Team: Philadelphia Phillies

Series: World Baseball Classic

Overall: 90

There’s not much to say on this one that everyone doesn’t already know. Kyle Schwarber was one of the best draft picks the Cubs have ever made. They shocked the world by taking a catcher from the Big Ten and signing him to an under-slot deal before transitioning him to primarily play the outfield so that his big left-handed bat could play. 

They decided to non-tender him after a disappointing 2020 only to watch him put together an all-star year the following season in Washington and Boston with 32 home runs. Since he left the Cubs, Schwarber has 94 homers and while the WBC version of him still isn’t a great defender in the outfield he is more than good enough to carry the DH spot if you’re going up against a RHP.