In Rebuilding Red Sox Rotation, Ben Cherington Faces Daunting Task

As new Red Sox GM Ben Cherington evaluates the available pool of free agent starters, he must be both underwhelmed and concerned. It will take significant dollars to sign the likes of CJ Wilson, Mark Buehrle, Roy Oswalt, or Edwin Jackson, the top free agent starters on the market this winter.

The Red Sox enter the offseason with just three proven starters: Josh Beckett, Jon Lester and Clay Buchholz. Consequently, Cherington is tasked with finding two additional starters, plus one or two reserves for the inevitable injuries that will occur over the long haul of a 162-game season.

Given how the Red Sox have fared in recent forays into the free agent pitching market with Daisuke Matsuzaka and John Lackey (both of whom have undergone Tommy John surgery and will miss most, or all, of the 2012 season), it is doubtful the Sox will be big spenders in the free agent pitching market this winter.

The talent pool just isn't particularly deep, or talented.

Adding CJ Wilson would represent a continuation of the high-priced free agent strategy that hasn't worked for the Red Sox to this point. Moreover, Wilson, who turns 31 this week, has been a starter for only two years.

The upside is that Wilson has thrown just 708 Major League innings through age 30. As a starter, the lefty has exceeded 200 innings in each of the last two seasons, while posting a 3.15 ERA in that span.

The downside is that this represents a very small sample size, and Wilson is going to command a huge salary based on this rather slim resume. Furthermore, scouts worry that Wilson's mechanics will lead to arm issues in the future.

Mark Buehrle is 32, has 12 seasons under his belt, and has already thrown an eye-popping 2,476 innings in his career. The lefty is undoubtedly an innings-eater, having exceeded 200 innings in each of the last 11 seasons.

But he is now past his prime and investing in a pitcher at that age, with that many innings, is an obvious risk.

Buehrle also pitches to contact and relies on an excellent defense behind him as a result.

Roy Oswalt is 34 and has two degenerative disks in his lower back. Red Flag.

For whatever reason, Edwin Jackson cannot stick with one club, having pitched for six teams since 2005.

No matter; the combination of Matsuzaka and Lackey has the Red Sox on the hook for nearly $27 million in salary next season, making it unlikely they will invest heavily for a fourth or fifth starter.

When you look at the available fourth and fifth-starter types out there — such as Chris Capuano, Bruce Chen, Aaron Cook, Jeff Francis, Freddy Garcia, Jon Garland, Aaron Harang, Rich Harden, Paul Maholm, Jason Marquis and former Red Sox Bartolo Colon, Brad Penny and Joel Piniero — it’s tough to get excited.

This is the reality that Cherington is faced with as he attempts to rebuild the rotation this winter. It is truly a daunting task.

As much as most Red Sox fans may not like it, it's fairly certain that Tim Wakefield (and his 5.23 ERA the last two seasons) will return in a limited role as an inexpensive insurance policy.

The Sox may also be forced to bring back Andrew Miller (5.79 ERA over six seasons) and the often-injured Erik Bedard as well.

Minor leaguers Junichi Tazawa and Felix Doubront could each be given the opportunity to start. However, Doubront is so undisciplined that he showed up out of shape at spring training this year and was soon injured, subsequently missing most of the season.

Unfortunately, as far as starting pitching is concerned, the pickings look slim right now.

There are differing reports on whether the Sox will get involved in the bidding for Yu Darvish, the latest Japanese pitching sensation. But we know how the last one worked out.

The Sox could always turn to a trade. The organization would gladly offer up any combination of Jed Lowrie, Josh Reddick and Lars Anderson for a starting pitcher. However, none of them has ever been an everyday player at the Major League level, meaning that they have limited trade value.

There has been much discussion about the possibility of trading Kevin Youkilis. However, his value is not high at the moment.

Youkilis will be 33 in March and batted just .258 this year. He has averaged 111 games played over the past two seasons. In fact, due to injuries, Youkilis, hasn’t played over 136 games in the last three seasons.

The third baseman also had just 111 hits each of the last two years. The troubling part is that Youkilis had 82 more at-bats in 2011 than in 2010. In addition, his homer totals over the last four seasons have spiraled downward: 29, 27, 19, 17.

The departure of Jonathan Papelbon virtually assures that Daniel Bard will remain in the bullpen. Perhaps that is best. Bard has never started in the majors, and the last time he did start was while playing Class-A ball in 2007. That season he posted a 7.08 ERA over 22 starts.

However, the Red Sox have told Alfredo Aceves to report to spring training prepared to be a starter, which is his preference. The club already controls him and he is a cheap alternative.

Such a move will necessitate yet another addition to the bullpen. Yet, as unreliable as bullpen pitchers may be, there are a lot more of them out there than useful starting pitchers.

While many people support the notion of making Aceves a starter, it should be noted that he posted a 2.03 ERA in 51 relief appearances and a 5.14 ERA in four starts.

Even if the Red Sox count on successfully converting Aceves, they will still need another starter to round out the rotation and two more for adequate depth.

That's a tall order. The Red Sox are not the only team looking for starting pitching and reserve depth this offseason.

Good luck, Ben Cherington. You've certainly got your work cut out for you.