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Even though the offseason has only just commenced for the San Francisco Giants and Detroit Tigers, general managers of 28 other teams already have been pondering their futures for some time.

For five GMs in particular, their jobs for the next three months are uniquely difficult, perhaps the most difficult in baseball. A variety of obstacles stand in their way of effectively making over their teams. They will have to hurdle those obstacles in order to improve their teams, and that’s easier said than done.

Here are the five general managers who have the toughest jobs this winter. For the Giants and Tigers, it’s finally time to rest. For these guys, their work has already started.


1. Brian Cashman, New York Yankees
Hands down, Cashman has the most difficult path facing him of any general manager of baseball. Perhaps it just comes with the territory of being the GM of baseball’s uber-team, but this offseason is especially difficult. With the Yankees’ mandate of “anything less than a World Series is failure” hovering over him, the fixes Cashman faces are not easy. Additionally, the Yankees are trying to get under the luxury tax threshold by 2014, and their best prospects are not close to contributing.

The Yankees have never had the luxury of going with a full-scale youth movement -- they are expected to contend every year, so Cashman must resolve the situation with Alex Rodriguez, whose declining skills, massive contract and no-trade clause make him nearly impossible to move. Picking up the contract options for Robinson Cano and Curtis Granderson was a good first step, but Mariano Rivera might retire and Rafael Soriano might opt out of his deal. And then you have Derek Jeter returning from injury, and who knows what to expect from Michael Pineda?

In other words, Cashman must retool a World Series contender with limited money, a fallow farm system and an aging roster rife with no-trade clauses. Toughest job, indeed.


2. Dayton Moore, Kansas City Royals
Moore can position the Royals as 2013’s version of the Baltimore Orioles or Oakland A’s. Position players Mike Moustakas, Eric Hosmer, Alex Gordon and Billy Butler are all ready to lead a playoff team. But Moore must completely rebuild his starting rotation, and to do that, he will have to make some uncomfortable decisions, including trading one of the aforementioned players.

Moore has talked about 2014 as the Royals' year to compete. But he has the talent to win now, and he should start by acknowledging the failure of Luke Hochevar. Dumping him would serve as a philosophical change for a club that has become enamored with “stuff” rather than results. While Danny Duffy and Jake Odorizzi are good pitching prospects, the majority of them have been way overhyped. Their only way to improve the rotation so quickly is to bring back Zack Greinke or sign Kyle Lohse or Anibal Sanchez and trade one of those young hitters. I know Moore has gone down this free-agent pitching path before, with the disastrous Gil Meche signing, but he can’t keep waiting for 2014. It’s time to win now.


3. Ben Cherington, Boston Red Sox
The fact is, nearly every move Cherington made last season did not work. From hiring Bobby Valentine, to trading Jed Lowrie to Houston and Kevin Youkilis to Chicago and Josh Reddick to Oakland, to the failed conversion of Daniel Bard to the starting rotation, it was a rough rookie year for Cherington.

However, what did work was the massive trade with the Los Angeles Dodgers that shed the Red Sox of Adrian Gonzalez, Josh Beckett, Carl Crawford and Nick Punto. That move shaved approximately $58 million in 2013 payroll alone. And with the acquisition of manager John Farrell, Cherington is effectively starting from scratch. And he’s on the clock now, too.

Cherington’s a bright guy and he will have ample opportunity to show what he can do with what almost amounts to a clean slate. He will have some cornerstones such as Dustin Pedroia and Will Middlebrooks, but he has to also hope Jon Lester and Bard return to form in their respective roles. His priority will be to figure out what to do with Jacoby Ellsbury, who is a free agent in 2013 and is represented by Scott Boras, so it won't be an easy negotiation. Cherington’s team has plenty of holes, and he will have some financial freedom, so there will be opportunities to show last season’s disaster was an aberration.


4. GM Mike Hill, president Larry Beinfest, Miami Marlins
It is a difficult situation when you’re the general manager of a ballclub, but not really the general manager, or when you're the president of a ballclub, but not really the president. Essentially, owner Jeffrey Loria calls the shots on all personnel decisions and managers, and Ozzie Guillen was the latest casualty. Don’t be surprised if outspoken outfielder Logan Morrison is next.

Of course, Guillen wasn’t without fault here, alienating the Cuban section of the Marlins’ fan base early last season. But after signing Heath Bell last winter and then trading him to Arizona, free agents will pause before going to Miami. So will managers who see no job security in South Beach -- in a span of six years, three managers (Joe Girardi, Fredi Gonzalez and Guillen) have held the job.

The Marlins will be competing with a resurgent Philadelphia Phillies team that still boasts the best rotation in the National League. The New York Mets will have lots of money coming off the books in time for the 2014 offseason and the Atlanta Braves and Washington Nationals are both built to compete for the next five years. But the Fish have some core pieces to work with, namely Mark Buehrle, Jose Reyes and Giancarlo Stanton, as well as some good youngsters in Rob Brantly, Jacob Turner and Nathan Eovaldi, as well as prospects Jose Fernandez and Christian Yelich. If Hill and Beinfest can do something this offseason with some autonomy, they could compete in the NL East.


5. Chris Antonetti, Cleveland Indians
When I say Cashman doesn’t have any money and is restricted by his payroll, remember the Yankees’ yearly payroll is near $200 million. Cleveland's 2012 Opening Day payroll was $65 million.

So Antonetti really doesn’t have any money, nor does he have much of anything else to work with. His hiring of Terry Francona as manager is a step in the right direction. But a manager will only win if he has winning players. The “best” pitching pieces he has to trade are Ubaldo Jimenez and Justin Masterson, who don't have a ton of value right now. His farm system is below average at best, with the exception of shortstop Francisco Lindor. Shin-Soo Choo, arguably Antonetti’s best player, is a free agent after 2013, and Boras is his agent. Antonetti simply can’t let Choo walk away for only draft-pick compensation.

Further, the AL Central is surprisingly deep with Detroit’s dominance, Chicago’s surprise and the Royals’ rise. Exacerbating things is his team and fan base seem to have lost faith in the front office, with closer Chris Perez openly criticizing him in the media. A rough road lies ahead for Antonetti and team president Mark Shapiro, whose own deal is up after 2013.