Ben Cherington: Predicting the 5 Busiest GMs at the MLB Trade Deadline

The waning hours until the July 31 trade deadline are arguably the most important of any during a general manager’s time in office.

Making and fielding calls from other general managers can take up a lot of time, but it is vital to either make your team a contender or to rebuild for the future.

With the second wild card added to this year’s postseason, several teams may consider themselves buyers instead of sellers. Whether or not that is true, every GM has a lot of pressure to go into August with a better ball club either for the present or for the future.

Each franchise’s GM will be busy come July 31, but which will be the busiest? Let’s take a look.

Ruben Amaro Jr., Philadelphia Phillies

The Philadelphia Phillies have several interesting debacles on their hands, mainly including the contract status and future of Cole Hamels.

Hamels’ contract expires at the end of the season and there’s some hesitation about whether he and the Phillies can come to an agreement on an extension. Philadelphia is planning to offer Hamels around $120 million to stay past this season, according to CBS Sports’ Jon Heyman.

Several teams have scouted Hamels lately, according to CSNPhilly.com’s Jim Salisbury, and even more have shown interest in him. Even if the Phillies sign a new deal with Hamels, Ruben Amaro Jr. could still be busy.

Cliff Lee would draw interest if he were available, according to Joel Sherman of the New York Post, but it’s unclear whether the Phillies would decide to deal the left-hander or not.

The Los Angeles Dodgers are interested in shortstop Jimmy Rollins, according to CBS Sports’ Danny Knobler, since Dee Gordon is out for a few weeks with a thumb injury.

Lastly, Heyman writes that Shane Victorino might not be in Philly for long as he’s sure to walk after this season if he’s not traded.

Amaro might not decide to trade any of these players, but he’ll definitely be busy fielding calls for them.

Jed Hoyer, Chicago Cubs

Theo Epstein, Jed Hoyer and the Chicago Cubs will attempt to refresh their Minor League system by trading some of their expensive veterans towards the trade deadline.

The biggest asset that Hoyer holds is pitcher Matt Garza, who is nearly guaranteed to be dealt. As ESPN Chicago’s Bruce Levine writes, Garza’s stock is increasing and several teams have scouted him recently.

Chicago could be looking to cash in big time for Garza, as they had a huge asking price during last offseason, according to FOX Sports’ Ken Rosenthal.

Another Cubs pitcher, Ryan Dempster, has drawn interest from at least ten teams, writes Levine. Dempster is having a great year and currently has a 33-inning scoreless streak.

Hoyer’s toughest task will be getting rid of Alfonso Soriano. Soriano has been good this season, but not many teams—if any—are asking about him, writes CBS Sports’ Jon Heyman. Part of the reason is because he’s under contract through the 2014 season and is owed $18 million each year.

The goal is to acquire as many decent prospects as possible for any of these three players. They’ll come out with at least two top-tier prospects for Garza and probably one for Dempster, but will likely just cut their losses on a deal involving Soriano.

Brian Cashman, New York Yankees

Brian Cashman and the New York Yankees will look for two pieces to add to their AL East-leading roster.

New York will explore deals involving a starting pitcher and have been linked to Francisco Liriano, according to CBS Sports’ Jon Heyman.

The Yankees will also keep an eye on the asking price for Cole Hamels, but will not pursue Zack Greinke, according to Ken Davidoff of the New York Post. The Yankees have a couple of injured starters at the moment and would benefit from adding a middle-of-the-rotation arm at the deadline.

New York is also in a small jam concerning their outfield. Brett Gardner has been out for a long period of time and have been getting by using Raul Ibanez and Andruw Jones regularly alongside of Curtis Granderson and Nick Swisher.

FOX Sports’ Jon Morosi tweeted that the Yankees have scouted outfielder Justin Upton, but later wrote that New York is one of the teams that Upton can block a deal to.

It will also be interesting to see what Cashman decides to do with Swisher. Even though their outfield is thin, it’s unlikely that the Yankees will give him a new deal after he hits free agency after this season, according to Joel Sherman of the New York Post. That could mean that they would be willing to deal him.

Cashman usually finds a way to come up big at the trade deadline and this year should be no different.

Ned Colletti, Los Angeles Dodgers

Under new ownership, the Los Angeles Dodgers are looking to put a World Series contender together—falling under the job description of Ned Colletti.

Matt Kemp and the Dodgers got off to a fantastic start to the 2012 season, but after Kemp suffered a hamstring injury, they got off track and now sit in second place in the NL West. In order to regain the top spot in the division, Colletti should make a push for some high-caliber players.

The Dodgers are one of the teams pursuing Cole Hamels and even though Los Angeles and Philadelphia have had discussions about a trade, the Dodgers might not have enough to acquire him, according to CBS Sports’ Danny Knobler.

Knobler also mentions a few other players that could interest the Dodgers including the aforementioned Matt Garza and Ryan Dempster as well as Michael Cuddyer and Josh Willingham.

With Dee Gordon sidelined with a thumb injury for several weeks, Los Angeles has started to pursue Jimmy Rollins to possibly replace him. That would not be a smart move for the Dodgers, since Rollins is locked in for three years and there isn’t a clear spot to put him once Gordon returns.

There’s a decent shot at the Dodgers picking up one of the two wild card spots in the playoffs which could be even more reason to make a deadline deal. 

Ben Cherington, Boston Red Sox

The Boston Red Sox are in an interesting spot—well out of the AL East, but very much still in the wild card race—and should be buyers over the next two weeks before the trade deadline.

Boston desperately needs a starting pitcher and could acquire either of the two aforementioned Chicago Cubs—Matt Garza or Ryan Dempster. Dempster is a much cheaper acquisition and the Red Sox are aggressively pursuing him, according to ESPN’s Buster Olney.

The Red Sox have also been linked to starter Francisco Liriano, according to CBS Sports’ Jon Heyman, as well as reliever Rafael Betancourt, according to Nick Cafardo of the Boston Globe, among others.

I wouldn’t expect a huge deal involving a big-name starting pitcher involving the Red Sox. Instead of going after guys like Cole Hamels, Zack Greinke or even Garza, I think they’re better off going after a guy like Dempster or Jason Vargas.

With Jacoby Ellsbury and Carl Crawford both back in the Boston lineup, the Red Sox have a lot of outfielders that they could end up dealing including Ryan Sweeney and Daniel Nava, according to Mike Silverman of the Boston Herald.

Boston backup catcher Kelly Shoppach has drawn interest from the New York Mets, according to MLB.com’s Peter Gammons, but I would highly suggest not dealing him in order to preserve Ryan Lavarnway until next season.

There is a ton of pressure on Ben Cherington to come out of this trade deadline with a team that can compete for a World Series. Can he live up to it?