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The Contractual State of the Starting Rotation

Entering 2010, the Boston Red Sox’s starting rotation boasted six World Series rings, five All-Star game appearances, both an American League Championship and World Series Most Valuable Player award and two no-hitters. Better yet, two of those starting five came into the early parts of the season having just inked fresh, multiple year contracts.

An impressive mixture of youth and experience -- almost all contractually locked-up for what is considered in the world of professional sports as long-term -- led many to believe that Boston would feature one of the MLB’s best starting rotations not only in 2010, but for the next few years as well.

It’s hard to find anything negative to say on the topic of having Jon Lester guaranteed in a Red Sox uniform through at least 2013, that’s for certain. However, that’s where the acclaim stops, or at least that of the unanimous nature.

With such an accolade-laden group commanding rotation spots for multiple seasons beyond 2010, would it be blasphemous to consider that the organization is actually worse off now than before they signed last off-season’s most coveted free agent pitcher, John Lackey, and extended the contract of Josh Beckett who, like Lackey, had won the deciding game of a World Series before he had reached the age of 25?

First, let’s take a look at the contractual statuses of the team’s ideal starting rotation at this particular point in time.

The off-season signing of John Lackey conjured as much skepticism as it did excitement in Boston. With a void to fill in the lineup due to the departure of Jason Bay, a power-hitting outfielder was clearly, according to majority opinion, the best way for the Red Sox to allocate their off-season spending allotment. Instead, they awarded the 31-year-old pitcher a five-year contract worth $86 million (including the $3.5 million signing bonus). During the duration of the deal, Lackey stands to make $18.7 million in 2010, followed by $15.25 in each of the remaining four years, with the club holding a conditional option for 2015 at the league’s minimum salary in the event that he would miss a significant amount of time as a result of a pre-existing elbow injury.

General Manager Theo Epstein made good on his promise to do everything in his power to re-sign Josh Beckett following the acquisition of Lackey; in early April the team extended Beckett’s contract through 2014. The four-year deal is worth a total of $68 million; $15.75 each season on top of a $5 million signing bonus.

After posting a high-bid of $51,111,111 in 2006 merely for the rights to a thirty-day negotiation window with Seibu Lions’ pitcher Daisuke Matsuzaka, the Red Sox managed to sign the international free agent to a six-year deal through 2012 worth $52 million. Matsuzaka, after making $6 million in 2007 and $8 million both this season and last, is promised $10 million in each of his contract’s final two seasons [2011-12] before becoming a free agent.

The lone left-hander of the group, Jon Lester extended his contract with the Boston Red Sox in March of 2009. The five-year contract worth $30 million total awards Lester $3.75 million this season, followed by sums of $5.75, $7.625 and $11.625 each of the next three. The Red Sox also hold a $13 million club option for 2014 (the option is void in the event that Lester finishes either first or second in Cy Young voting anytime from 2009-13 and is subsequently traded).

Lastly, but perhaps most intriguing, is pitcher Clay Buchholz. Buchholz makes just $443,000 here in 2010, but is arbitration-eligible for the first time following the season. Despite being a model of inconsistency his initial few full seasons in Boston, Clay has been arguably the team’s most reliable pitcher this season en route to a team-best fourteen wins and an American League-best 2.36 ERA through his first twenty-one starts. Though he is currently the only member of the rotation who isn’t guaranteed at least two more seasons in Boston, contractually speaking, the organization’s reluctancy to part with Buchholz during trade negotiations, even before his recent on-field maturation, means that it’s just a matter of time before he, too, is signed to a long-term deal.

Clearly, the Red Sox value starting pitching, and with good reason. After all, as the old adage goes, ‘pitching wins championships,’ and in Boston’s case, it had better.

The Red Sox were owners of the second highest opening day payroll in Major League Baseball this season -- only behind the Yankees -- at $162,447,333. Of those who comprise the ten highest 2010 payrolls, Boston’s 33.34% increase from where it stood the season prior ($121,745,999; 4thin MLB) is only surpassed by that of the Minnesota Twins, who experienced a 49.4% increase from 2009.

That same value placed on starting pitching is the driving force behind such a substantial increase in payroll. For instance, the combined 2010 salaries of those five pitchers is $43,326,333, which equates to 26.67% of the team’s entire payroll.

Ironically, it’s been Buchholz and Lester -- owners of the group’s two lowest salaries -- that have offered the most return this season. Lester’s 2.80 ERA and 13 wins are second on the team only to Buchholz’s 2.36 ERA and 14 victories. Both appeared in their first All-Star games in 2010 and are amongst the league’s top-five in ERA. With neither turning the age of twenty-seven until Lester does so in January, the future bodes well in Boston as long as these two are around.

Conversely, the rotation’s two most disappointing performers thus far have been the two oldest and highest-paid, Josh Beckett and John Lackey.

Beckett spent a significant amount of time on the disabled list this season, starting just thirteen games for the Red Sox and going 3-2 with a 6.51 ERA. Opponents are hitting .294 off of Beckett and he’s allowed 91 hits in 76 innings -- compare that to Buchholz, who has surrendered just eighteen more hits in 133.3 innings. Beckett has also amassed career-worst marks in ERA+ [67], WHIP [1.539] and H/9 [10.8].

Lackey, the Red Sox’s prized off-season acquisition, hasn’t quite delivered as Boston had hoped in the first of his five-year deal. While he’s proved durable, starting 24 games and alleviating concerns over any lingering effects of his previous elbow injury, it’s his effectiveness in those starts that has left something to be desired. The 10-7 record currently held by Lackey is hardly indicative of how he’s pitched. His 4.54 ERA is the highest it’s been since 2004 and his SO/9 [5.8] and ERA+ [96] are the lowest since that same year. He’s also set career-worst marks in WHIP [1.519], H/9 [10.2] and SO/BB [1.68]. Plus, in his twelve starts at Fenway Park this season, a place he figures to pitch at a lot in the next few years, opponents are hitting .299 off him. Not exactly what you’d expect from your highest paid starter, especially after just signing him to a five-year deal worth a large sum of money.

With both Lackey and Beckett contractually locked-up through 2014 at a collective $31 million per season, and judging by this season, the future may all of the sudden appear a bit more grim despite the presence of both Lester and Buchholz.

So, with Lackey’s signing initially leading many to believe that management wouldn’t opt to bring Beckett back to Boston following 2010, the question is, why did they?

Well for one, there doesn’t figure to be a surplus of available marquee starting pitchers in 2011. By securing both Lackey and Beckett in what was originally assumed to be a defense and pitching oriented ‘bridge year’ anyway, the organization seemingly had intentions of acquiring what they believed to be an imposing 1-2 punch at the front end of the rotation while the market offered it, rather than waiting and potentially having to deal the prospects that they were attempting to ‘bridge’ to in the first place in search of a quick fix down the road. Besides, if the organization was under the impression that starting pitching help internally was a few years from fruition, and rightfully so, then it was hard to argue against a veritable bridge consisting of Josh Beckett, Jon Lester and John Lackey to help get them there.

Not to mention, at the time that Beckett’s deal was extended, Buchholz had yet to truly establish himself as a reliable option that they could count on. Had they known that Clay would carry-over the success he had towards the end of last season and pitch as well as he has to this point in 2010, they may have thought twice about reconfiguring Beckett’s contract. Entering the season, the Red Sox assumedly believed they had three starters that they could rely on -- Beckett, Lackey and Lester -- had they known they could complete that list with Buchholz’s name rather than Beckett's, it appears less likely that they’d have felt it necessary to designate so much money towards extending Josh. A front of the rotation in 2011 consisting of Lester, Lackey and Buchholz now looks just as appealing as one that includes a 30-year-old Beckett when you consider the remarkably cheaper price tag accompanying it; that’s an additional $15.75 million dollars that the Red Sox could have used each of the next four seasons on other areas of need -- perhaps a some bullpen help or an extension of Clay Buchholz’s contract?

However, here Boston stands, owing over $30 million per season over the next four years to a pair of thirty-something pitchers who are becoming increasingly regarded as undependable even before they've had a chance to spend their signing bonuses.

All that without even a mention of Daisuke Matsuzaka’s return on investment, simply because it’s almost too frustrating to touch on and would require an entire article itself to address all the issues.

And yet, as mentioned earlier, the rotation isn’t without its bright spots. Jon Lester has emerged as one of the most dominating left-handers in the league, and thanks to Buchholz’s expedited development, Theo Epstein now appears to have been correct in sticking with the once struggling young pitcher, even through temptations like Roy Halladay and Adrian Gonzalez.

That being said, what can the Red Sox ultimately expect from their core of starting pitchers for the next few seasons, or the duration of their current deals?

The success and production of both Beckett and Matsuzaka remain heavily contingent on health.

Daisuke has flashed the ability to be a dominant starter but has yet to put it together consistently. This season, however, was the first in which Matsuzaka really showed a determination to get back to the level of play that made him a legend in Japan. He came into the spring with a visably altered attitude and if he can stave off the injury bug for the entirety of 2011, we may finally see him morph into the player we paid so handsomely merely to speak with -- the operative word there being, if.

There’s no questioning Josh Beckett’s drive and desire to compete at the highest level. Unfortunately, durability and health aren’t exactly things you can have complete control over. Whether it be blisters or back spasms, Beckett had seen his fair share of time on the disabled list due to injuries more typical of your average 30-year-old beer league softball player than those of a professional athlete. When he’s healthy, however, his prowess is well-documented. The only other time he failed to start at least thirty games for Boston in a single season, he came back the following year and won nineteen games. The poor results from both an individual and team standpoint this season should give Beckett some extra motivation in 2011. However, beyond that, one has to question how each additional year with effect his terrible luck with nagging, minor injuries. In his first five seasons with Boston, including 2010, Beckett has turned in just two quality seasons from an overall standpoint. As his age increases, so does the feeling that we may be lucky to get even another two good seasons out of his new four-year deal; at almost $16 million a season, will it end up being worth it?

With Lackey, it’s difficult to imagine him regaining his 2007 form that saw him go 19-9 with a league-best ERA [3.01] and ERA+ [150]. However, while he has never won more than fourteen games (aside from 2007) and only averaged 25.5 starts in the two seasons prior to joining Boston, the durability questions that ultimately led to the conditional club option in his deal with the Red Sox seem to have dissipated, and he’s back on track to being the pitcher that started thirty-three games in each season from 2003-07. Before coming to the Red Sox, Lackey had a string of five consecutive seasons with a sub-four ERA. What has saved him to some extent this season has been his ability to induce the ground ball with men on base, if he can continue to do that while getting back to his typical SO/BB ratios, Lackey could still potentially have some of his best seasons in a Red Sox uniform. The problem being, even his best seasons may not be able to justify the type of money that Boston invested in him.

As far as Lester and Buchholz go, it wouldn’t at all be a stretch to expect things to only get better from these two production-wise.

Lester has already cemented himself as a certified ace at the age of just twenty-six. Because he has been elected an All-Star, thrown a no-hitter and clinched a World Series title in such a short period of time, people forget that he is still developing and learning how to pitch at the major league level. His mechanics and frame make it hard to imagine injury concerns creeping up on him at any point and his immunity to prolonged struggles makes him one of the most reliable pitchers in baseball. And again, he’s just twenty-six years of age.

Buchholz is an interesting case. Having hardly pitched one full season at a consistently high level, he’s still already being regarded as one of the league’s better pitchers. With an arsenal of pitches as devastating as the one he was blessed with, it was simply a matter of time before the talents outweighed whatever had plagued him to this point. Despite taking the scenic route, it appears Buchholz is finally at the stage Lester was just a couple seasons ago -- enjoying a breakout year and beginning to establish himself within the context of the league’s other great pitchers. It won’t be long before Boston locks Buchholz up long-term and fans can begin an annual "Lester or Buchholz for staff ace" debate.

Overall, the Red Sox seem to have effectively solidified their rotation for a good deal of years to come. However, that may not necessarily be entirely positive. With so much importance on starting pitching -- and such a large percentage of the team’s overall payroll invested in it -- it’s hard to feel good about something so heavily dependent on virtually uncontrollable factors; those of course mainly pertaining to health.

When healthy and productive, the Red Sox have arguably the best starting rotation in all of baseball. However, it’s a different story when not -- which, unfortunately seems to so often be the case.