Chicago Cubs: Could have been the Cubs instead of the Astros
This imaginary trade might be the most difficult to sell into reality, even given hindsight, because of the fact that the Cubs would have had to convince (and maybe overpay) for a guy who pitched for a division rival. It’s hard to believe that the Cubs price wouldn’t have been substantially higher because they were also in the NL Central, but maybe the Pirates wouldn’t have cared at that point, instead looking to rebuild as much as possible while getting rid of a guy they didn’t think they’d be able to resign once he became a free agent. (They wouldn’t have)
Gerrit Cole is probably the best pitcher on the planet right now, but in Cubs lore, he will forever be remembered as the guy who got smoked in the 2015 Wild Card game (You do remember that Schwarbomb into the Allegheny, right?). And, granted, that’s a wonderful memory for Cubs fans, as it was essentially the beginning of the Cubs run to the 2016 World Series. However, it’s not really fair to Cole, as he’s become even better than he was then, and he had to go up against the greatest pitcher on the planet in 2015 in that game.
While Jake Arrieta and Schwarber may have gotten the best of Cole that day, Cole has gotten the last laugh as he was able to parlay his time with the Astros into a sparkly new $324 million contract with the Yankees this offseason.
If the Cubs could have figured out a way to make the Pirates an offer (two or three high-level or top prospects) in the offseason before the 2018 season, they would have enjoyed two seasons of ace-level Cole rather than signing Yu Darvish or Tyler Chatwood. And while Cole, like Verlander before him, may have gained something in going to the Astros, even a reasonable facsimile of his work the past two seasons would have propelled the Cubs to the playoffs in both of the last two seasons. We didn’t even talk about any financial ramifications due to the fact that Cole made less than Chatwood the last two seasons. Yikes.