With the Red Sox and Yankees both set up to be 95 to 100 win teams for the next few years, does it make sense for the Jays to start selling? With nearly a quarter of their schedule against the beasts of the east, and only one wild card in play, the best move for the Jays might be to start a 3-5 year rebuild now. The Twins can help with that, with a deep system full of potential high upside guys. Even better, if the Jays are tearing down, they’ll probably be looking for more lower level guys, rather than immediate big league help, which lets the Twins keep their now open window, well, open. To the Trade: Twins get—Josh Donaldson and Marcus Stroman Jays get—Fernando Romero, Wander Javier, Akil Baddoo, Blayne Enlow, and Alex Kiriloff Why the Twins do it: adding Donaldson improves the infield defense, while allowing Miguel Sano to focus exclusively on hitting. A Dozier-Mauer-Donaldson-Sano-Rosario-Buxton-Polanco-Kepler-Castro lineup could potentially be one of the best in the league. Adding Stroman to the rotation gives you a solid top 3 with Santana and Berrios, and you still have Mejia and Gonsalves as back end options with upside. It allows Falvey and Levine to focus on bullpen arms, which at that point would be the weak spot on the team. And finally, it would send a clear message to the casual fan that this new administration is different, and serious about winning. Why the Jays do it: as mentioned above, Toronto seems to be looking at a closed window for contention right now. Acquiring young, cheap, controllable assets for 2021-2023 makes sense. Of the 5 guys above, at least one is a Top 100 guy now, and quite possibly all 5 will be by the end of the year. With all of them except Romero at least a couple of years away, the Jays have time to continue building out a wave that can overtake the spent-out Boston/New York teams of the early to mid ‘20’s. What are your thoughts, armchair GM’s?