So, we’re all sitting here with a post-cinderella hangover after our 5 year run, since we’re the worst team in baseball and stuck in rebuilding at least through 2019. So I had a thought on that: are you really mortgaging your future by trading prospects to extend your playoff chances? The Orioles traded 3 years worth of decent major league pieces (Hader, Ariel Miranda, probably a few others) but no top tier prospects. Still, that price wasn’t nothing. However, now that we’re rebuilding, we’ve got the 5 for 1 in the Machado trade, and Britton is almost certainly getting moved, and there’s an outside chance that Gausman, Brach, and a few other players get moved as well. While some of this is predicated on having tradeable pieces, this assumption is somewhat covered by the fact that, if you are in a pennant race, you probably have some talented players on your roster that helped you get there. There’s also a timing component here, in terms of starting to suck when your window is about to shut and you can start entertaining deadline trades. By both criteria here, it seems to have worked out pretty well for the Orioles. And while we were never good from 1999-2008, we still managed to develop Bedard, who netted us 30 WAR worth of all-star level talent in Tillman and Jones. And obviously those players were pretty integral to our success in 2012-2016.
Conclusion: I no longer really think that you’re mortgaging your future by trading your minor league talent away in a playoff race, because if you’re trading for pieces to help you in a pennant race, that means you already have some good players. And if you have good players, you can always trade back for young controllable talent when things don’t roll your way.