It can take years before a trade can be judged. At the trade deadline, however, the priority for a contending team is to "win now," and its side of the trade will be rated heavily on the end-of-season result. Unless the team goes deep into the playoffs, the deal will be scrutinized heavily for years as the players involved either live up to, fall short of or exceed expectations while with their new organization.
While you can't blame Los Angeles Angels general manager Jerry DiPoto for trading three of his best prospects—shortstop Jean Segura and pitchers Johnny Hellweg and Ariel Pena—from a very thin farm system to acquire Zack Greinke from the Milwaukee Brewers in July 2012, the Angels have clearly lost that trade.
Greinke, who signed a free-agent contract with the Los Angeles Dodgers after the season, pitched well but the team fell short of the playoffs.
The Angels were aggressive, which isn't a bad thing, and they put themselves in a position where they might've been the favorite to win the World Series had they made the playoffs. But they didn't make the playoffs.
Segura has become a star in Milwaukee (.334 BA, 11 HR, 9 2B, 8 3B, 23 SB), and Hellweg will make his MLB debut on Friday after allowing just three earned runs and 22 hits in 33 innings over his past five Triple-A starts.
As bad as things have gone for the Brewers in 2013, they came out on the good side of that deal.
A lot had been invested in the 2012 Angels team with Albert Pujols and C.J. Wilson signing massive free-agent contracts prior to the season, so expectations were high. Signing Josh Hamilton before this season didn't ease the pressure on DiPoto, and Hamilton's struggles have only made things worse.
Without the resources down on the farm, he'll have a tough time adding to his 25-man roster by the trade deadline. This could be his chance, however, to make a couple of "under the radar" deals that, if they work out, could put him back in good standing as the team's general manager. If not, his tenure could be a short one in Anaheim.
Here are four other general managers under pressure to win big in the 2013 trade market.