Red Sox Starting Rotation Outlook: Ryan Dempster’s Decision Offers Clarity

Ryan DempsterThe Boston Red Sox have no shortage of starting pitching depth, even in the wake of Ryan Dempster’s shocking announcement.

The Red Sox were expected to progress through spring training with six veteran starters — Jon Lester, Clay Buchholz, John Lackey, Felix Doubront, Jake Peavy and Dempster — vying for five rotation spots. Instead, Dempster announced over the weekend that he will not pitch in 2014, giving the Red Sox some clarity on what the rotation will look like to begin the regular season.

Dempster might have been the odd man out, anyway. But the 36-year-old’s decision not to pitch this year still came as a surprise, as he’s leaving $13.25 million in guaranteed salary on the table. He said he felt he was not prepared physically and personally to pitch.

The Red Sox now have some extra financial flexibility they can use to bolster their roster before Opening Day or facilitate in-season transactions.

The Red Sox’s five-man rotation appears set, but Dempster’s departure could give Boston’s younger crop of starting pitchers more opportunities. After all, rotations tend to get jumbled throughout the course of a 162-game grind.

Let’s take a look at the Red Sox’s starting rotation situation for 2014 and beyond.

Depth chart

1. Jon Lester
2. Clay Buchholz
3. John Lackey
4. Felix Doubront
5. Jake Peavy

Barring something unforeseen, the Red Sox’s starting rotation will be comprised of Lester, Buchholz, Lackey, Doubront and Peavy to begin the season. The only question is where everyone slots in.

Lester, Buchholz and Lackey almost certainly will man the top three spots, meaning manager John Farrell must decide where Doubront and Peavy will slide in at the back end. Given that Doubront is younger and has a higher ceiling at this point, he should grab the No. 4 spot with a steady spring. Plus, Doubront is a left-hander, so splitting up Lester and him with a right-hander in between makes sense.

It’s rare that every starter stays healthy for an entire season, so having depth beyond the top five is important. Dempster’s exit certainly lessens the Red Sox’s depth to some extent, but Boston has plenty of up-and-coming pitchers capable of filling the void, even though they don’t have the same level of experience.

Brandon Workman, who thrived as a starter and reliever last season, likely will begin the year in the Red Sox’s bullpen. The plan is for him to be stretched out during spring training, though, and he’ll likely be considered the Red Sox’s sixth starter and fill in when necessary.

Drake Britton, Rubby De La Rosa and Allen Webster all saw action at the major league level last season, and they, too, could factor into the Red Sox’s 2014 starting rotation plans when the situation calls for it.

Anthony Ranaudo, Matt Barnes and Henry Owens are other candidates to keep an eye on, although Ranaudo is the only one of the three currently on the Red Sox’s 40-man roster.

Points of optimism

-Lester showed last season that his tumultuous 2012 campaign was a fluke. The left-hander went 15-8 with a 3.75 ERA in 33 regular-season starts in 2013 after going 9-14 with a 4.82 ERA in 33 starts in 2012.

-Lester reinforced the notion that he’s a big-game pitcher last October. The 30-year-old went 4-1 with a 1.56 ERA in five playoff starts, including two fantastic World Series performances in which he outdueled St. Louis Cardinals ace Adam Wainwright.

-Buchholz said upon arriving in Fort Myers that he’s feeling good physically, and that it’s largely because he implemented a new offseason regimen.

Buchholz, who dealt with neck and shoulder issues last season, heeded the advice of Dr. James Andrews and got plenty of rest this offseason so he could report to camp without any lingering discomfort.

-Buchholz was terrific last season when healthy, so the potential certainly is there for him to be an ace-caliber pitcher.

Buchholz’s 1.74 ERA in 2013 matched Pedro Martinez’s 2000 ERA, which is the lowest mark for a Red Sox pitcher with at least 100 innings pitched since 1920. Buchholz, who posted a 2.33 ERA in 2010, is one of only three major league pitchers since 2010 to have two seasons of at least 100 innings with a sub-2.50 ERA — joining Clayton Kershaw (2.28 in 2011, 1.83 in 2013) and Roy Halladay (2.44 in 2010, 2.35 in 2011).

-Tommy John surgery seems to have done Lackey wonders.

Lackey, who showed up to spring training in great shape last year, finally looked like the pitcher the Red Sox thought they signed before the 2010 season. Lackey put together a very good regular season, then followed it up with a big-time postseason in which he even pitched the World Series-clinching game.

-Lackey, whose stuff was much better than in previous seasons with the Red Sox, set a career-high in 2013 with a 4.03 strikeout-to-walk ratio.

-Lackey went at least six innings in a career-high 15 straight games at one point last season. In other words, he consistently gave the Red Sox quality outings.

-Doubront was very solid for a three-month stretch last season. He allowed three runs or fewer in 16 straight starts, matching Babe Ruth for the longest such single-season streak by a left-hander in Red Sox history.

-Doubront had ups and downs last season, but he ended the year on a high note by coming up big in relief during the World Series. It looked like a fire was lit under Doubront, whose struggles down the stretch led to speculation about whether he’d be included in the Red Sox’s postseason plans.

-Doubront, who turned 26 in October, still is young, so it’s possible he hasn’t reached his full potential yet.

-Peavy is entering his first full season in Boston. There could be some added comfort for the veteran.

-Dempster’s exit gives the Red Sox a whole bunch of financial flexibility.

The Red Sox were very close to the $189 million luxury tax threshold with Dempster’s $13.25 million salary on the books. Now, the Sox are right around $176 million to begin the year, according to WEEI.com’s Alex Speier.

-The Red Sox have plenty of young, intriguing starting pitching options beyond their top five starters. That should give the Red Sox some peace of mind going into this season, while also allowing them to be flexible in the future.

-Workman became a key member of the Red Sox’s bullpen by the end of last year. The 25-year-old didn’t allow an earned run in 8 2/3 innings in the playoffs, and Farrell clearly trusted him in high-leverage situations despite his minimal big league experience.

Workman pitched well in three starts, too, though. He went 1-1 with a 2.45 ERA in a starting role, showing the same poise and mound presence that made him a force in the pen. Farrell absolutely would have no problem handing Workman the ball in a starting role this season if necessary.

-Webster has tremendous stuff, including a high-90s fastball, an excellent sinker and a solid changeup. The 24-year-old had control issues during his time in the majors last season, but the potential certainly is there.

-De La Rosa also has electric stuff that’s headlined by a high-90s fastball. The 24-year-old still was working his way back last season in his first full year following Tommy John surgery, but there shouldn’t be any restrictions this season.

-Britton’s future is hard to project, mainly because the Red Sox thrust the young left-hander into a relief role last season. He pitched well, though.

-Ranaudo enjoyed a great bounce-back season last year after his 2012 campaign was derailed by an injury. The 24-year-old went 8-4 with a 2.95 ERA in 19 starts with Double-A Portland, then went 3-1 with a 2.97 ERA in six appearances (five starts) with Triple-A Pawtucket. He’s once again a prospect to watch.

-Barnes showed progress following a late-season promotion to Triple-A last year, so the 23-year-old is entering 2014 with something to build on.

-Owens is widely considered the Red Sox’s most untouchable prospect not named Xander Bogaerts. The 21-year-old is a tall lefty whose body is still filling out, but Owens was unhittable at times last season.

Points of skepticism

-Lester becomes a free agent after this season. While Lester has made it clear he’d like to remain in Boston and that he won’t let his impending free agency become an issue as he prepares for the 2014 season, it’s still going to be a hot topic for as long as he plays under his current contract.

-Lester likely will be paid like an ace. But is he really an ace?

Lester is a very good pitcher who has, for the most part, been consistent outside of 2012. It’s hard to completely overlook that shaky season and some occasional struggles from last season, though.

-Buchholz’s health has been an issue. It’s hard to feel confident that he’ll provide the Red Sox with 30-plus starts this season, even if he’s feeling 100 percent healthy to begin spring training.

-Buchholz’s new offseason plan included more rest than usual, meaning he’s currently playing catch-up. It remains to be seen if the new regimen has any negative side effects.

-Lackey was terrific in 2013. Will the same version show up in 2014?

-Doubront often looks like a reliable major league starter. Other times, however, he looks disinterested, with walks and high pitch counts being his biggest imperfections. This year could go a long way toward showing the Red Sox what they really have in Doubront.

-Peavy proved to be a nice addition down the stretch last season, but he was unimpressive in the playoffs. It’s hard to feel overly confident about him taking the ball in a big game despite his bulldog mentality.

-While the Red Sox seemingly have the horses to withstand the loss of Dempster, the club’s other options all are young with little or no major league experience. In other words, they mostly are unknown commodities at this point despite whatever flashes they have shown.

Reasonable expectations for 2014

A lot of things went right for the Red Sox last season, but reliable starting pitching was one of the biggest factors in the team’s success. Red Sox starters, who went a combined 67-42, ranked sixth in the majors in innings pitched (984) and third in WAR (15.9), consistently giving the club a chance to win.

It might be naive to assume the Red Sox’s starters will improve upon that success in 2014, but a repeat performance seems reasonable given Boston’s overall rotation depth. While an injury or two to the starting rotation can cripple many teams, the Red Sox are well-positioned to handle the unforeseen issues that inevitably will be thrown their way over the course of a 162-game season.

The Red Sox’s offense also should be potent enough in 2014 to overcome any temporary lapses in starting pitching production.

Position beyond 2014

Buchholz, Lackey and Doubront are under contract beyond 2014, so it’s reasonable to assume they will be around after this season.

The biggest question, obviously, centers on Lester and his impending free agency. Lester has made it perfectly clear that he’d like to remain in Boston beyond this season and that he’d accept a hometown discount to make it happen. The Red Sox still will need to pony up a decent chunk of change, though, so it’ll be interesting to see if the front office backs off its recent reluctance to hand out lucrative, long-term contracts.

Peavy also will be a free agent after this season, and it seems unlikely he’ll return unless he puts together a very good year. The Red Sox have a surplus of young starting pitchers, and they’ll need to take the training wheels off at some point.

The Red Sox’s 2015 rotation likely will consist of at least one or two of the following group: Workman, Britton, Webster, De La Rosa, Ranaudo, Barnes and Owens.

The Red Sox also could use their young starting pitching depth to facilitate a major trade, whether during the season or next winter. Boston’s financial flexibility will help in that regard, too.

Down on the farm

Notables: Webster, Britton, De La Rosa, Ranaudo, Barnes, Owens, Dalier Hinojosa, Steven Wright, Trey Ball

Workman will begin the year in the majors in a relief role. Britton and De La Rosa are candidates to join him in the bullpen, although Triple-A is a more likely Opening Day landing spot for those two hurlers.

Britton, De La Rosa and Webster are in play to be called up at any point, as they are on the 40-man roster and have major league experience. Steven Wright is an option, too, although he hasn’t arrived in camp yet because of a sports hernia procedure.

Ranaudo and Barnes could become major league starting options later in the year. Ranaudo likely would receive a call first — if all things are equal — because he’s currently on the 40-man roster. Calling up Barnes, who is not on the 40-man, would require the Red Sox to make a corresponding roster move.

Owens could test the Red Sox’s hand if he continues his dominance at Double-A and/or Triple-A, but 2015 seems like a logical timetable for his first meaningful big league contributions.

Hinojosa, a Cuban defector who signed with the Red Sox in October, is worth keeping an eye on this spring, although his future might be in the bullpen.

Trey Ball, who is just 19, still has a lot of developing to do, but the Red Sox think very highly of the 2013 seventh overall pick.

Editor’s note: NESN.com will provide an organizational outlook for each position in the days leading up to the Red Sox’ first full-squad spring training workout. The schedule for the outlooks is below. Click the links to view each outlook.

Monday, Feb. 10: first base
Tuesday, Feb. 11: second base
Wednesday, Feb. 12: third base
Thursday, Feb. 13: shortstop
Friday, Feb. 14: outfield
Monday, Feb. 17: catcher
Tuesday, Feb. 18: starting rotation
Wednesday, Feb. 19: bullpen

Have a question for Ricky Doyle? Send it to him via Twitter at @TheRickyDoyle or send it here.

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