Chicago Cubs: Five trades that could have created a dynasty

Chicago Cubs: Do you realize how little the Reds gave up for this guy?

On January 19, 2017, the Reds traded Dan Straily to the Marlins for Luis Castillo. Oh, and the Marlins also threw in Isaiah White and Austin Brice too! Funny thing is, Dan Straily actually pitched for the Cubs in 2014 before going to Houston and Cincinnati. To be fair, Straily wasn’t awful for the Marlins in 2017 and 2018, but he also wasn’t very good- certainly not as good as his exquisite 2016 season for the Reds.

He also wasn’t enough for the Marlins to get for Castillo, who has gone on to become a stud for the Reds. You’re telling me the Cubs didn’t have someone of Straily’s ilk to send to the Marlins in 2017 for Castillo?

Did I tell you Castillo only just turned 27 years of age and won’t be a free agent until 2024 as well? Yeah, that’s super depressing. Imagine Castillo as that cost-controlled young stud in the rotation for the Cubs for five more years. Makes guys like Alzolay, Brailyn Marquez, and Justin Steele look even more promising, right?

As with the Brewers acquisition of Yelich (again, from the Marlins), this trade especially hindered the Cubs because the real trade was made by a Central division rival. Take away Castillo from the Reds and place him on the Cubs and you kill two birds with one baseball.

In addition, as with the team friendly deal Yelich is on currently, a trade for Castillo also would have ameliorated the Cubs current financial woes and would have allowed them to spend money more efficiently in the bullpen or for a second baseman rather than for both Chatwood or Darvish. Heck, maybe if the Cubs had managed to swing a couple of these deals, they already would have extended Cole and set themselves up with a rotation of Cole, Castillo, Hendricks, Lester, and Quintana.

That’s with Yelich in the outfield too.

Hey, we can dream in the midst of a second straight boring Cubs offseason, right?

While this look into imaginary trades was inane and seemingly without any relevance, it does point to the importance of pulling off the right trades, at the right time, with the right players – and certainly does prove that one or two trades can change the course of otherwise successful or down-on-their-luck franchises. Or, you know, make a Cubs dynasty.