Why Red Sox GM Ben Cherington Is in Way over His Head in Boston

Two weeks ago, the best word to describe the Boston Red Sox was "disaster." Other words like "catastrophe" and "calamity" would have been fine too.

The Red Sox are no longer a disaster. They enter Thursday on a two-game losing streak, but their starting pitching could be a lot worse and there seems to be at least some semblance of order in the bullpen. Their offense has slumped in the last two games, but the Red Sox will not have any trouble scoring runs on a consistent basis this season.

But three days into the month of May, can anybody look at the Red Sox and honestly say that they look like a playoff team?

The answer is no. Collectively, they don't have enough firepower to compete with the Tampa Bay Rays and the New York Yankees, and the case can be made that even the Toronto Blue Jays and Baltimore Orioles are better teams.

The Red Sox will have to get stronger as the season moves along, and that task falls on general manager Ben Cherington.

That's a thought that should not inspire confidence. Cherington may have spent several months as Boston's co-GM in 2005-2006, but he's essentially a rookie general manager. He's obviously not an idiot, but his tenure has been underwhelming to this point.

The Red Sox were not exceedingly proactive in terms of bringing in players this offseason. Cherington took his time making moves, and the moves he did make didn't make huge splashes. Unfortunately, a couple of the moves he did make haven't panned out.

Case in point, the Mark Melancon trade. Melancon had a very good season pitching for the Houston Astros last season, but the American League greeted him by pounding him for 10 hits and 11 earned runs in just two innings of work. He was supposed to be a key piece of Boston's bullpen, and now he's in the minors trying to figure things out.

When Cherington traded for Andrew Bailey, he knew he was getting an injury-prone reliever. Sure enough, Bailey injured his thumb and is going to be out for most of the season. It's not Cherington's fault that Bailey injured his thumb, but he did know that he was rolling the dice with Bailey.

Cherington's biggest failure this offseason, however, was his failure to strengthen Boston's starting staff by bringing in a solid veteran. He instead went for bargain options like Aaron Cook and Vicente Padilla, and the lack of reliable back-end options took forced standout reliever Daniel Bard and inefficient lefty Felix Doubront into the rotation. Both of them have been good, but their inability to consistently go deep into games is going to put a lot of pressure on Boston's weak bullpen.

Fortunately, the bats Cherington added have panned out. Cody Ross has had the power stroke going, Ryan Sweeney has been better than advertised and Mike Aviles has been much, much better than advertised. Hats off to Cherington for those moves.

In retrospect, though, it should come as no shock that the Red Sox are as weak as they are at this point in the season. They started the season as a weak ballclub, and injuries have only made them weaker. 

Worse, you get the sense that Bobby Valentine is not only learning how to be a manager again, but is also learning how to manage in this day and age. When the Red Sox introduced Valentine in December, Cherington praised him (via ESPNBoston.com) for having an "enormous baseball intellect." He spoke too soon.

It won't be easy for Cherington to patch Boston's holes and make them into a playoff contender for the stretch run. What they need is pitching, both in the starting rotation and in the bullpen, and the simple fact of the matter is that the Red Sox are short on in-house options.

Cherington could trade for pitching (or sign Roy Oswalt off the scrapheap), but he's facing a dilemma. The Red Sox do not have a lot of talent in the upper levels of their farm system that they can deal, and their system as a whole is weaker than it's been in quite a while. A true "splash" trade would require Cherington to give up a significant package of prospects, and that's something he should be hesitant to do seeing as how the team in front of him is not one that will become a championship contender with one or two quick fixes.

To save this present team, it's just not worth it to compromise the club's future.

And that's a completely different headache. Cherington will soon have to make decisions on several key players. It will be his call whether to pick up Youkilis' $13 million club option for next year, and the time will soon come when he'll have to sign Jacoby Ellsbury to a long-term extension. That will not be an easy call given Ellsbury's injury woes in recent seasons, and it's certainly worth noting that he is represented by Scott Boras.

To boot, Cherington may find himself looking for teams to take Carl Crawford off the organization's hands. His $142 million contract has become an albatross, and it will be in both Crawford's and Boston's interests to cut ties if he struggles again upon returning from injury this season. If the Los Angeles Dodgers come calling, and Bill Shaikin of the Los Angeles Times thinks they could, Cherington may have no choice but to listen.

When you look at the Red Sox from a big-picture perspective, you can easily see that the future is just as uncertain as the present. The organization is in a bit of a no-man's land right now. There is no clear path to a brighter tomorrow.

This has to be a big reason why former GM Theo Epstein felt comfortable leaving. He said during his Chicago Cubs introduction (see ESPNChicago.com) that he wanted to make the Cubbies into World Series winners, the same challenged he embraced with the Red Sox.

Epstein did build a World Series winner in Boston. Two of them, in fact. He built a mini-dynasty that looms large on the landscape of baseball history.

That dynasty, such as it was, is crumbling. It's Cherington's job is to either keep it standing or to break it apart and build a completely new dynasty of his own. No matter which option he chooses, he will do so in front of a highly critical New England audience.

Even a master general manager would be in over his head, and Cherington simply hasn't earned the right to be called a master general manager.

Not yet, anyway.

If you follow me on Twitter, I'll give you my thoughts on your team's GM in just 140 characters.