That's actually not accurate. The only prospect of note the Cubs traded before winning the World Series was Gleyber Torres. Where the Cubs traded away their minor league depth was defending their World Series title and defending their division title last year. Since winning the world series they made the following trades: Dan Vogelbach and Paul Blackburn for Mike Montgomery Jorge Soler for Wade Davis. Dylan Cease and Eloy Jimenez for Jose Quintana Jeimar Candelario for Justin Wilson The players they picked up last year: Cole Hamels, Daniel Murphy and Brandon Kintzler they basically absorbed the salary commitments to those players and gave up fringe prospects from the low minor leagues. The Cubs are in the spot they are in because Epstein hasn't been able to replicate his draft success from Boston. He did pick Kris Bryant third overall (but I imagine 29 other baseball execs would have too). His other first round picks include one player who is solid: Kyle Schwarber, a platoon CFer in Albert Almora and several busts and of course some prospects where its too early to tell. None of Epstein's 2nd round picks have made an impact with the Cubs, and the only other Epstein Cubs draft pick to see significant time is 18th rounder David Bote. How this applies to the Brewers is they've already traded away more prospects than the Cubs (although some of those Cubs prospects were of higher quality) to acquire Swarzak, Yelich, Soria, Moustakas and Schoop. They traded Ryan Cordell, Lewis Brinson, Jordan Yamamoto, Isan Diaz, Monte Harrison, Kodi Medeiros, Jorge Lopez, Brett Phillips, Luis Ortiz and Jean Carmona. So the next wave of Milwaukee prospects is already gone. Further, as Epstein has proven its much harder to find blue chip prospects when drafting near the bottom of the round. I don't think the Brewers system is stocked with many blue chippers to begin with, and the window to compete is not going to get any more open. Therefore the GM has to balance where he feels the team is and where they can go, and if the deal makes sense I wouldn't hesitate pulling the trigger wondering about an inevitable rebuild that will likely occur after Stearns is already gone or on the way out.