The baseball offseason, the winter, is designed so that teams that did well can improve, teams that just missed the mark can finally reach the playoffs, and teams that sucked can try to not finish in last. But there is also a flaw. Baseball is still a business, and the way it is covered in TV, the team with the flashiest signings "wins" the winter, which has unfortunately become the goal of many teams. The last time a team the "won" the winter and won the World Series was in 2009, when the Yankees spent hundreds of millions of dollars on five people, only one of whom is still on the Yankees, and he is doing very poorly. In order to "win" the winter, you need to destroy your future, like those poor Padres (soon to be those poor DiamondBacks). They "won" the winter by trading away all of their prospects and giving tons of money to people that should have been going into prospects. Instead of having a future, the Padres have Matt Kemp.
Teams have to be able to resist the urge that the media provides to trade the future for approval. Look at the last five World Series winners. The Cardinals, Giants, and Red Sox all found roll players, who they didn't pay too much and won the winter by fitting into what their organization wanted. The Royals I have already made a post on, but they also didn't spend gobs of money and talent (once you trade talent, it's gone forever). They made smart decisions, and that is how you really win the winter.
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