Edwin JacksonBen Cherington and his underlings will be spending the early part of this week getting ready to head to Palm Springs, CA to take part in this year’s annual General Manager’s meetings. While the GM Meetings aren’t normally a time of excessive wheeling and dealing, this is the time where the seeds of those deals generally get planted. How will this year’s meetings play out? Who knows. But one thing is for sure, the Red Sox need to add some starting pitching to their rotation and with a newfound sense of financial flexibility, it looks like the Red Sox brass will be looking to make a move. It could be a trade, but with some viable options available on the free agent market, Cherington might want to consider hanging on to his prospects and instead open up the check book if the price seems right.

Today, we’ll take a look at some of the pitchers who would fit best in Boston and pontificate as to where they might fall in the overall equation. Let’s jump right in:

Best Pitcher on the market: Anibal Sanchez: Yes, Zack Greinke is the best pitcher on the market, but I’m not so sure he’s on the Red Sox radar. I think for the sake of what’s interesting to Ben Cherington and company, Sanchez is probably the best bet. And hey – from the Red Sox perspective, there’s a lot to like.

Sanchez has quietly been one of the more steady pitchers in baseball, accumulating 11.6 fWAR over the past three years (an average of 3.8/year). His strikeout rate seems fairly strong even though last year’s spike was more of an outlier than the norm. His walk rate is improving and there doesn’t seem to be too much noise created from volatile luck statistics.

Sanchez couples his decent K/9 with a higher GB% and low FB%, both of which should play well Fenway. His velocity is headed in the right direction, especially considering there’s no two-seam noise to dilute it. He’s demonstrated durability over the past few years and is mostly even-steven when it comes to his home & road and L vs. R splits. Sanchez’s numbers imply he’s a strong number two but in Fenway and the AL east it wouldn’t be unfair to scale his expectations back to a solid #3. Still, that’s what the Red Sox would be looking for, although other suitors who play in more Anibal-friendly parks would be more aggressive in trying to sign him.

As with any pitcher, there does seem to be some reason for a little caution, particularly his higher LD%. His durability could also be interpreted on the flip side as being a guy who’s racked up a lot of miles and may be due for an injury soon. The shoulder injury in the past seems to be very much in the rearview mirror but should at least be duly noted, as anyone would do with a high-workload, young starting pitcher.

The second potential issue is – of course – Boston. While Sanchez has spent some time in the organization, a lot has changed since then and Fenway Park is a far cry from the quiet, cushy confines of Miami and the dutiful loyalty of the Detroit press. Sanchez has been able to blend into the background in both Detroit and Miami, taking a back seat to both Justin Verlander and Josh Johnson. In Boston however, he’ll be seen as a potential solution. Will he be able to handle the scrutiny and focus of being a player that everyone has their eyes on? Time will tell.

Dave Cameron pontificated that Sanchez should get a deal similar to Mark Buehrle’s 4 year, $52 million deal. That’s probably a low estimate. Considering Sanchez’s age and the fact that his skills are all trending in the right direction, I wouldn’t be at all surprised to see him command closer to $60 million, if not eclipse it altogether. Relative to the market, 5/$75 wouldn’t surprise me in the least for the right team. Sanchez is a good pitcher to be sure, but he might be too rich for Boston’s blood.

Best fit that isn’t: Dan Haren I read a really interesting piece over at Beyond the Box score a few days ago that made a pretty compelling case that the only issue with Dan Haren was his lower back issues and that he was a pretty strong candidate for a bounce back year in 2013.

Lots of good points were brought up, including:

• That his back injury could have caused the poor performance in his otherwise reliable sinker
• That his swinging strike % dip this year isn’t room for too much concern as that’s where it sat from 2008-2010
• His control still seems to be there
• His 2011 numbers didn’t seem to imply any luck, meaning that 2011 is probably closer to the real Haren than the 2012 version.

All of that I can buy on a certain level; but considering the way his trade fiasco went down over the weekend, there’s room for more than a little skepticism.

The question is obvious: If this is all driven by the back injury and his numbers point to him being a prime bounce back candidate in 2013, then why don’t the Angels want him? And that’s not just any other ‘we’ll pass’ scenario. They were literally willing to take Carlos Marmol – and the money owed to him – in return.

Sure, there’s a chance that the deal with the Cubs could have fallen apart over issues unbeknownst to us. It could be 28 other teams not wanting to cannonball into the pool because they see no reason to give anything up in order to get him – knowing full well Angels General Manager Jerry DiPito was going to decline his option, anyway. It could also just be because the Angels want Zack Greinke really, really, really bad.

But how eager the Angels were to let Haren go – and particularly what they were willing to take on in order to flip him, should raise some eyebrows.

Dave Cameron nailed it in a piece yesterday, citing the example of Ryan Madson last year, where the Phillies backed out last minute to sign former Red Sox closer Jonathan Papelbon. It seemed like everywhere you turned, other teams didn’t see Madsen as a priority and before we knew it, he was forced to take a small pillow deal with the Reds that resulted in his elbow exploding in Spring Training and was followed quickly by season-ending Tommy John surgery. Could it just be that teams saw something in his medicals that made them pass? Or was it just bad luck and a case of a team preferring one player to the other?

Either way, I wouldn’t want the Red Sox to pay to find out. If they get late into the offseason and there’s nothing else to look at, then maybe he’s worth a gamble. To me, he seems like an operation waiting to happen. If 28 other teams don’t think he’s worth a $10 million salary dump AND Carlos Marmol, then the Red Sox shouldn’t either. I’d stay away.

Best value: Hiroki KurodaIf the Red Sox are looking for a safe bet that won’t blow the bank without getting stuck in a long-term commitment, then Kuroda is their man. I wrote this about him last year and I’ll be darned if I wouldn’t change my analysis at all.

First a little background… Kuroda seems like a pitcher who’d fit well within the confines of Fenway – even at an advanced age. He rarely walks anyone (2.1 BB/9) and gives up even fewer home runs (1.07/9). He’s more ground ball oriented than he is a strikeout pitcher, but has really good stuff despite not having a ton of velocity (in fact, he had the 9th highest swing and miss % in baseball in 2010). He uses a splitter as his strikeout pitch and throws two versions of a slider. His swing and miss % out of the strike zone is impressive to say the least.

His age is a double-edged sword. On one hand, you almost wonder if the bottom is going to fall out – but so far there doesn’t appear to be any indication that it will. The upside is that other pitchers have entered the ‘sexier’ category and Kuroda might be the guy who slips under the radar as a better value. I think he could certainly be had on a 2-year deal around $11-$12 per. Throw in some old man incentives and that might get the job done.

Big issue for now seems that he’s pretty much settled on either pitching for the Yankees again next year or heading back to Japan to wrap up his professional career. I’d particularly bank on the later given that A.) His remaining skill is likely to last longer there than it would here; and B.) It makes business sense to reintroduce himself to the Japanese market in preparation for his pending retirement and all those deodorant commercials he’ll be doing once he gets there. Long story short, the money might not be as up front there as it is here, but it probably lasts longer. You’re also competing with the Yankees, which we really don’t want to do right now.

Stay away from: Kyle Lohse This guy is a sabermetric time bomb. Let’s sum this up in one, nice, neat – albeit smelly sandwich:

• He’s heading into his age 34 season
• LOB% was high
• BABIP was low
• HR/FB% has been mostly low. Thank Busch Stadium.
• 3 seasons of steadily climbing LD%
• 5 seasons of steadily declining GB%
• Even his FB% is down and it’s all heading to his LD%
• Uncharacteristic success with a FB that is characteristically crappy.

Put this guy in any hitter’s park – never mind Fenway Park, and grab a vomit bag. Everything is headed in the wrong direction. Thankfully, some idiot will pay him 3-4 years and $50-$60 million. I just hope it’s not the Boston brain trust. To be totally truthful, I don’t know if there’s a pitcher on the market I’d do more to stay away from.

Don’t sleep on: Scott Baker Before he got hurt, everything about Scott Baker was headed in the right direction. BB/9, K/9, FIP, xFIP – everything. While Target Field may have exacerbated the uptick a bit, he’s still probably a 3.70-3.80 FIP pitcher. While he went down with season ending elbow surgery last year, the UCL checks out fine. The surgery was to remove scar tissue, so with a mostly clean bill of health, there’s no reason to think he can’t bounce back.

His downside isn’t much, but should be considered. With April & May ERA’s of 4.86 and 5.01, respectively, Baker is a notoriously slow starter and might blow out a lot of good will in Boston if he can’t hit the ground running. Baker also posts high FB%’s, which could spell trouble too if his stuff is a little flat at first. Still, I think if people are patient with him, he could prove to be a very valuable asset as the year progresses.

I’d say that of the 1-year turn and burn pitchers on the market, Baker’s probably the best option. His injury is the most distinguishable and there aren’t any troubling trends on the track record. On a contending team with a bigger ballpark, he could be flat out deadly. Whether he wants to come to Boston or not remains to be seen. I can see him getting a one year deal at around $6-7 million, but I’m confident enough in his upside that if the Red Sox (or anyone, for that matter) went as high as $8.5 to $9 million, that I wouldn’t bat an eyelash.

Going dumpster diving: Roy Oswalt The negotiations around Roy Oswalt last year were at best juvenile and at worst- flat-out absurd. Right from the get-go, Oswalt established very tight boundaries on who, what, where and how he was going to pitch and everyone needed to fall in line or beat feet. Too bad for him, everyone did –at least at first. Lucky for Oswalt, the Rangers got a little desperate, signed him, created a bit of a glut in their rotation and Oswalt had what could be called – and this is putting it nicely – a lost season.

While 2012 was a self-inflicted wound of sorts for Oswalt, 2013 could prove to be productive provided he approaches things in a more flexible fashion – especially with regards with where he’s willing and able to go. In fact, with a full spring training to prepare and an early exist form the market to get settled, Oswalt could be a bounce back candidate.

There are also some statistical rays of hope from last year’s performance– albeit in a small sample size. His walk rate and strikeout rates were both strong. He was incredibly unlucky, posting sky-high HR/FB%’s, low LOB% and an over-inflated BABIP. Even with Oswalt’s slight decline during his back-injury-riddled 2011 season, no one could have predicted an explosion that was as bad as he was last year. It seems to me that it was a combination of poor luck and poor preparation provided the obvious.

I wouldn’t pay a lot to grab him, but with a more deliberate routine, a better offseason and some flexibility on Oswalt’s part about where he’s willing to go and whom he’s willing to talk to, he might be one of the biggest surprises of this offseason.

Who I’d want: Edwin Jackson In looking at the Red Sox rotation I see almost nothing but question marks. Will Jon Lester shake two so-so seasons and transform back into the ace we all thought he could be? Clay Buchholz has been as good as he’s been bad. Can he find consistency? Was Felix Doubront’s drop off due to him hitting an innings ceiling or is it an indication of his actual ability? Who knows what we’ll get out of John Lackey?

With a team with so many questions in general – especially regarding their rotation – I think it’d be advisable to land a player who can bring a little more consistency to the roster. Jackson seems to me to be that guy.

Jackson has been somewhat of a pitching gypsy over the years, finding himself playing all over the league including Los Angeles, Tampa Bay, Detroit, Arizona, Chicago, St. Louis and just this past season – Washington. The history is self-explanatory. Jackson is a useful albeit unexceptional arm. He chews innings, gets strikeouts and is as quintessential a #3 starter as they come. His high walk rate and prone-ness to HR’s has prevented him from getting the multi-year deal he probably deserves, but it’s not for nothing. Jackson has been an increasingly reliable starter as he’s matured.

How reliable? Reliable enough to place him 25th in fWAR among Starting Pitchers with at least 450 IP since 2010. That’s a good enough to best the likes of Madison Bumgarner, Tim Lincecum, Wandy Rodriguez, Gavin Floyd, Josh Beckett, Matt Garza, Chris Carpenter, Shaun Marcum, Jake Peavy, Ryan Dempster and Hiroki Kuroda. His xFIP of 3.74 is better than Jared Weaver, C.J. Wilson, Johnny Cueto, Matt Cain, Chad Billingsley and Ian Kennedy.

There’s been a lot made of the Red Sox pursuing 1-year pillow-contract types with the hopes that they find their past magic and turn into valuable assets. To be honest, that approach – given the current state of the rotation – would seem redundant to me. In fact, there are a lot of talented pitchers coming off of poor performances on this team. It’s not exactly something in short supply on this roster. Yes, there’s room to be optimistic about bounce backs. Yes, there’s plenty of promise on its way from the farm system. But right now, that’s all it is – hope & promise. There isn’t anything close to a sure bet. Edwin Jackson isn’t a sure bet – but he’s as close to one as there is outside of Greinke and Sanchez.

Jackson is a pitcher who’ll throw 175 innings. He’ll strike out 150ish batters. He won’t burn you with walks. He’ll give you a chance to win every five days and more often than not, will be better than the guy he’ll be up against.

Jackson isn’t a world-beater. He’s not an ace. He’s not the ‘answer’ to a rotation in need of many of them. But he is what this team doesn’t have right now – a guy who can provide solid production with a track record of success in a variety of environments, in the prime of his career and experience well beyond his years. To me, he’s exactly the kind of guy the Red Sox should be going after. If they can grab him for anything less than $50 million, they should do it in a heartbeat.