Free agent signings of Josh Hamilton and Albert Pujols have put DiPoto under constant pressure to win now.
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.
It was evident that starting pitching was the Kansas City Royals' top priority this offseason. After general manager Dayton Moore was done adding pieces to his 25-man roster, it was clear that it was really their only priority. But he went all-out to upgrade what was a clear weakness.
Within six weeks, Moore had acquired Ervin Santana from the Angels for minor league reliever Brandon Sisk, re-signed veteran Jeremy Guthrie to a three-year, $25 million deal and traded away top prospect Wil Myers in a deal with the Tampa Bay Rays that brought back two more starting pitchers, James Shields and Wade Davis.
Not only were the Royals paying four-fifths of their rotation an estimated $31 million in 2013 alone, he also gave up one of the best power-hitting prospects in baseball, two pretty good pitching prospects (Jake Odorizzi and Mike Montgomery) and another lower-level minor leaguer to complete the deal with the Rays.
The results have been mixed thus far.
While the rotation has been much improved and an obvious strength, the team is 35-39 and six games back of a playoff spot. Moore looked like a genius when the team started 17-10. Then he looked like the worst general manager as his team lost 16 of its next 22.
And now he's brilliant again during the team's latest 13-7 run.
In all seriousness, Moore will need to add another bat to his very inconsistent lineup—either a second baseman or an outfielder—by the trade deadline, and he might have to be creative if he doesn't want to trade away any other top prospects, including shortstop Adalberto Mondesi and pitchers Yordano Ventura and Kyle Zimmer.
He does have some starting pitching depth with Danny Duffy recovered from Tommy John surgery and back in Triple-A, Felipe Paulino not far behind in his recovery from the same surgery and two starting pitchers—Bruce Chen and Luke Hochevar—the Royals currently have working out of their pen.
There are some things Moore can do, and there are some interesting players who could be available in the next few weeks, including Chase Utley and Nate Schierholtz. If they fail to break .500 this season, things could get ugly in Kansas City, and Moore could be the fall guy.
New Dodgers ownership, after taking over in 2012, gave general manager Ned Colletti the go-ahead to add a ridiculous amount of money to the team payroll. After acquiring big-name players with big-money contracts like Josh Beckett, Carl Crawford, Adrian Gonzalez, Zack Greinke and Hanley Ramirez, Colletti had ensured his team would have the highest payroll in baseball going into the 2013 season.
But it hasn't worked out up until now.
Of that group, only Gonzalez has been able to stay healthy and productive, although he's no longer the power threat he had been with the San Diego Padres a few years back. The re-signing of Brandon League has been disastrous and has also served as a reminder of some of Colletti's worst signings over the years.
Not only did they fall short of a playoff berth last season, they've been in the NL West cellar for most of this season. Pressure is on Colletti to turn this team around and get back into the playoff hunt.
At 34-42, they're surprisingly just seven games back in the division. They're far from out of it, and Colletti's fate as the Dodgers GM has yet to be determined. International acquisitions Yasiel Puig and Hyun-Jin Ryu are doing what they can to help save his job, but he'll need to do much more than hope that his team gets healthy and starts playing a lot better than it has.
Sure, that will probably need to be a big part of it.
But there are some gaping holes at third base—Aramis Ramirez and Michael Young could be targets—and in the rotation—Scott Feldman or Ricky Nolasco could be a fit— that will need to be filled if the Dodgers going to bounce back and get into the playoffs.
And if they do, Colletti will keep his job and be hailed as the greatest general manager in the game.
It's still too early to determine whether the Philadelphia Phillies will be "buyers" or "sellers" at the trade deadline.
Of course, general manager Ruben Amaro Jr. will have a tough time admitting his team is a "seller" after it came back from the dead and into playoff contention last season after he traded away starting outfielders Hunter Pence and Shane Victorino in late July.
And this is probably why Amaro won't be making that decision of "buyer" or "seller," at least not alone. Ownership will ultimately need to let Amaro know which direction to go.
If he gets the go-ahead to add to his 25-man roster, he better hope his team makes the playoffs or is at least a very strong contender that is clearly better after his trade deadline dealings.
The Phillies have a need in the rotation with Roy Halladay's status uncertain for the remainder of the season. The bullpen is also in need with setup man Mike Adams out for the year.
Adding a productive outfielder could also help down the stretch.
If Amaro's lucky, a productive outfield acquisition might erase the memory of this past offseason when he non-tendered Nate Schierholtz, who is having a career season with the Chicago Cubs (.926 OPS, 11 HR, 32 RBI), and signed Delmon Young (.667 OPS) to be his right fielder. Never mind. That will probably never be forgotten.
At 37-41 and 7.5 games back of a playoff spot, the Phillies are closer to "buyers" than "sellers" right now.
If they happen to fall back into a double-digit deficit, Amaro will likely try to trade free agents-to-be Carlos Ruiz, Chase Utley and Michael Young while considering the possibility of moving Cliff Lee, Jonathan Papelbon and/or Jimmy Rollins for young players who can help in 2014 and beyond.
If the Phillies keep Amaro around for the remainder of his contract, which runs through the 2015 season, his July 2013 trades will likely play a major factor in his staying beyond that.