Two years ago Red Sox general manager Theo Epstein foresaw a hole in the franchise's plans for starting pitching. The Brad Penny and John Smoltz experiments of the previous season had failed. Beloved prospect Justin Masterson had been dealt at the trading deadline for catcher Victor Martinez. Clay Buchholz was at last emerging as a solid contributor to the rotation, but after him there wasn't much coming up through the farm system. Felix Doubront maybe. Future top prospect Casey Kelly, only one year removed from high school, was still far away from the majors and though drafted as a pitcher was still trying to be a shortstop.
Meanwhile the forecast for free agent pitchers looked grim in the coming years. Angels ace John Lackey was the only good pitcher hitting the market that offseason. The next year Cliff Lee would be the only arm available of any foreseeable quality. The year after that, this year--well, C.J. Wilson is now the only decent option but was still a reliever two years ago. So after the 2009 season, Epstein was looking at three consecutive years of lean pickings on the free agent market for starters, precisely at a time when the farm wasn't going to be offering much help in that regard.
As the rotation stood two offseasons ago, emerging ace Jon Lester was signed for four to five more years. Rotation leader Josh Beckett was signed for one more year and was a candidate for an extension. Daisuke Matsuzaka was signed for three more years. Young Clay Buchholz was under team control for several years to come. First-time All-Star Tim Wakefield was hanging out in the clubhouse in his boxers reading magazines.
So what did Theo do? Well, smartly he tried to acquire Matt Holliday to play left field in place of free agent Jason Bay. Reportedly he offered the 30-year-old a five-year contract worth $82.5 million. The Red Sox would find themselves out of the running, however, for that offseason's biggest prize. Holliday would eventually get seven years, $120 million from his most recent team, the Cardinals. Turning from those sweepstakes Theo devoted the team's money to setting in place the pitching rotation through the coming lean years. There was one ace on the market and Theo successfully offered him that same five-year, $82.5 million deal. John Lackey's contract then proved a template for Beckett's four-year extension, as the two Texan righties would then be given equal pay for equal time to play for Boston. Providing the franchise a rotation of Beckett, Lester, Lackey, Matsuzaka, and Buchholz/Wakefield for multiple seasons while the farm worked on new arms seemed to be a good job done by the general manager. This seemed especially so after the failed Penny and Smoltz experiments.
The Lackey years, however, have been disastrous. Even when his peripherals weren't atrocious for a couple months at the end of last season, key injuries and other game factors did their best to prevent wins. And John Lackey's 2011 season as a starting pitcher represents a new nadir in Red Sox history. Meanwhile Beckett, Matsuzaka, and Buchholz have had lost seasons due to injury, and the farm has predictably not picked up the slack--even worse so than expected as Doubront has been worthless. Unthinkably the Red Sox have missed the postseason two years in a row. Only the offense has kept the team above .500.
I would say hopefully now that we are somewhere near half-way through the lean years that Theo Epstein foresaw two years ago. For one thing, the three-year free agent drought comes to an end next year as Cole Hamels, Zack Greinke, Matt Cain, Brandon McCarthy, Shaun Marcum, Anibal Sanchez (a former Red Sox prospect included with Hanley Ramirez in the deal for Beckett and Lowell), Colby Lewis, John Danks, Jeremy Guthrie, Francisco Liriano, and others are all scheduled to hit free agency at the same time that Daisuke Matsuzaka comes off the books for Boston.
But more importantly the farm system holds lots of promise for starting pitchers beginning to emerge sometime hopefully around 2013-14. The best hopes had once lain with top prospects Casey Kelly, first of all, and after him Stolmy Pimentel and Drake Britton. But Kelly was traded for Adrian Gonzalez last December and the latter two took major steps backwards this year. They wouldn't, however, be the first major-league pitchers who had lapses while developing, and there remains hope for Pimentel and Britton. Likewise Junichi Tazawa, who returned from Tommy John surgery this year, could still see his once-promising career pan out. Brandon Workman and Raul Alcantara are esteemed highly enough by the organization that they were deal-breakers in the Rich Harden trade with the A's this July. A year ago failed reliever Manny Delcarmen was through the magic of alchemy (a trade with the Rockies) turned into prospect Chris Balcom-Miller, about whom you will hear mixed reports but some people are supremely impressed by what they see. Best yet, though, the last two drafts have brought in two high-ceiling college pitchers Anthony Ranaudo and Matt Barnes*. It is upon these two now that most hopes are riding for the franchise's future.
*Matt Barnes in a way fills the void of Justin Masterson in the system. Masterson with two others was traded for Victor Martinez, who upon signing with the Tigers last winter netted for the Sox the draft pick that was used for Matt Barnes.
But none of these prospects will be ready next year. As the Rays continue to debut a new stud each year in Jeff Niemann (2008), David Price (2008), Wade Davis (2009), Jeremy Hellickson (2010), and Matt Moore (2011), the Red Sox farm has nothing. Boston's rotation is in turn either atrocious, overpaid, underperforming, disabled by injury or some combination thereof. These are the Lackey years. Theo Epstein was quoted by Tom Verducci recently as saying in regard to the latest moneyball market inefficiencies, "I've been giving the same answer for years. It's keeping pitchers healthy and it's better drafting." Ironically, this is precisely how the Rays beat the Red Sox this year, and likely how they will beat them next year.