On the surface, this trade makes sense. The Cubs are trading away their top prospect plus a few others with good potential to shorten games when the postseason rolls around. Whichever inning Aroldis Chapman pitches in is the inning you can take to the bank. However, you could argue that they’re giving up way too much of the future for a rental relief pitcher.
Of course, it doesn’t matter if they win the World Series. You trade any prospect in any system if you are guaranteed to win your last game of the season. Chapman probably gives the Cubs a 5-10% better chance at being crowned for the first time in a billion years. I think even Theo would tell you that the Yankees are getting the better end of this deal. That doesn’t mean this wasn’t the right trade to make. The Cubs could be very confident that they’ll resign Chapman when he tests free agency anyways.
Just look to the West side to see a similar situation. The Blackhawks rented Andrew Ladd with the cost being a first round pick and a talented young player (who was supposed to be the prize of the Saad trade). No Cup means the trade was a failure. If they find a way to come back in Game 7, we wouldn’t be saying that. Same goes with the Cubs this year.
Fortunately for the Cubs that’s not exactly comparing apples to apples. They have the best young talent in the game right now and it’s all cost controlled for quite a while. The Hawks have the best core in the league but it’s aging quickly. The Cubs can afford to overpay in a trade to try and ensure a championship. Even if they’re overpaying for what seems to be a pretty bad guy.