Ranking the best free agent pitching targets

This represents part two of a five-part analysis of the 2015 Red Sox rotation. Part one looked at the arms that carried the team through 2014, while part two examines the free agent market for potential fits. These rankings do not rank players by talent. Ben Cherington has shown an unwillingness to exceed five-year deals with significant price tags. No player has been excluded by a projected contract, but their position in my rankings reflects the team’s ability to sign them. Players are also categorized into two segments, those who are “true aces” and those who would be a “wingman” to an ace.

Honorable Mention: 

8. Max Scherzer

Sep 15, 2014; Minneapolis, MN, USA; Detroit Tigers starting pitcher

(37) gets ready to deliver a pitch in the fourth inning against the Minnesota Twins at Target Field. Mandatory Credit: Jesse Johnson-USA TODAY Sports

Scherzer is easily the best starting pitcher that will be available this winter. He is also 30 years young, has strikingly low mileage on his arm and is coming off two Cy Young-caliber seasons. He wants and will probably get a seven year deal worth over $150 million dollars. A team will give it to him, and they might even win a World Series with him, but at some point, they will no longer want to pay him $25+ million dollars a season. My guess is they will start to grow concerned as he turns 34, and will be in full on panic mode when the clock strikes 35.

He is going to break the bank for some team this offseason and barring a complete reversal of GM Ben Cherington’s spending philosophy, I don’t expect that team to be the Red Sox.

7. Edinson Volquez

Sep 3, 2014; St. Louis, MO, USA; Pittsburgh Pirates starting pitcher

(36) throws to a St. Louis Cardinals batter during the first inning at Busch Stadium. Mandatory Credit: Jeff Curry-USA TODAY Sports

Volquez has been a man on a six-year mission. A highly touted prospect, he was acquired in the package that sent Josh Hamilton to Texas. In his first full season as a Red, he achieved startling success to the tune of 206 K’s, a 17-6 record,  3.21 ERA, 1.33 WHIP, and a whopping 4.5 WAR. He followed this debut with two very similar seasons both of which were stunningly mired in mediocrity, the first of which ended in Tommy John surgery midseason, while the second included a 50-game suspension for the use of performance enhancing drugs. In his final season in Cincinatti, he regressed further, notching a 5.71 ERA and -1.5 WAR.

He was then sent to the pitcher friendly PetCo Park, as part of the package that brought Mat Latos back from San Diego. He made some improvements in his first season with the Padres, accumulating a 4.14 ERA, the best number he had put up since his rookie year, but again regressed to the point of his release by San Diego. After a brief, unproductive stint with the Dodgers, he was given a prove-it contract from the Pirates this past offseason, and boy did he prove it.

Volquez set new career marks in ERA and WHIP, with a 3.04 and 1.23, and put up 2.6 WAR. Pittsburgh has become a career revitalization stop for pitchers in recent years so it remains to be seen if he can replicate those numbers or if he will again regress. To me, he is a little too risky coming off arguably the best year of his career to go along with a history of regression. Somebody will give this man a raise this offseason but I would be surprised (and a little concerned) if it was the Red Sox.

6. Brandon McCarthy

Sep 17, 2014; St. Petersburg, FL, USA; New York Yankees starting pitcher

(38) reacts after he gave up a solo home run during the fourth inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports

McCarthy, liked many of the other names on this list, is a pitcher who has experienced significant ups and downs in recent years. This is not a coincidence; these are exactly the types of players Cherington locks in on, and will be targets to watch this winter. McCarthy was a journeyman to start his career, with unmemorable stops in Chicago (White Sox), and Texas before finding his footing with the A’s in 2011. McCarthy pitched like an ace in Oakland, with 4.9 WAR and maintained an ERA in the low 3’s (3.32 in 2011, career best 3.24 in 2012) before he promptly skipped town for a lucrative contract with the Diamondbacks.

Unfortunately, like many pitchers do, he crashed and burned in the hitter-friendly Chase Field as a D-back. After scuffling in his first year, he really plummeted this past seaso,n leading to the Yankees taking a flyer on him this summer. Like Volquez, McCarthy was one who paid dividends, nearly single-handedly leading the Yankees on what became Derek Jeter‘s final playoff push. McCarthy brought a 5.01 ERA over from Arizona, but achieved a 2.89 ERA while wearing pinstripes. McCarthy has a history of injuries, including concussions, which will rightfully give many teams pause. But, this type of aggressive signing is right in the new front office’s wheel house, and were it not for a recent report that he wants to return to New York next spring, he would likely be higher on this list.

5. Justin Masterson

Aug 3, 2014; St. Louis, MO, USA; St. Louis Cardinals starting pitcher

(63) talks with starting pitcher

(41) during the seventh inning against the Milwaukee Brewers at Busch Stadium. The Cardinals defeated the Brewers 3-2. Mandatory Credit: Jeff Curry-USA TODAY Sports

Masterson, who started his career in Boston before being traded to the Indians in the Victor Martinez deal, has experienced quite the up-and-down career. As of late, the still young (29) right hander has struggled far more than he has prospered.  His best season to date came in 2011, when the then-25 year old Masterson took the American League by surprise, racking up 14o Ks, a 3.21 ERA, 1.28 WHIP and 3.6 WAR along with his first career shutout.

Unfortunately for the former Indians ace, he was never able to replicate or improve on those numbers, and in two of the three seasons since then he finished with an ERA well above 4.50 (4.93 in 2012, and a downright hideous 5.97 in 2014). He was dumped by the Indians at this year’s trade deadline, as his struggles had reached the point where the former ace was doing far more harm than good. The Cardinals took a flyer on him and, as has been the case with Allen Craig here, it has not exactly panned out. He stunningly put up worse numbers in the National League, and there are serious questions as to whether he will ever be the same pitcher if he couldn’t find a rhythm outside of the hitter-friendly American League.

But as is the case with Clay Buchholz, Masterson is talented and may be worth one more chance. Masterson never achieved the level of success Buchholz did, but beyond that there are few reasons not to give him the same benefit of the doubt. Rob Bradford of WEEI reported that the team only plans on targeting one top-tier free agent pitcher this offseason, but Masterson’s value has plummeted to the point where he will be signed to a low risk, prove-it deal. With his age, his familiarity with Fenway and his talent (however inconsistent) Masterson makes a lot of sense for the Red Sox this offseason. The two pitchers behind him have put up much better numbers, but Masterson seems far likelier than either of them.

4. Ervin Santana

Aug 13, 2014; Atlanta, GA, USA; Atlanta Braves starting pitcher

(30) walks off of the field after the sixth inning during their win against the Los Angeles Dodgers batter at Turner Field. The Braves won 3-2. Mandatory Credit: Jason Getz-USA TODAY Sports

Santana represents arguably the best combination of attainability and talent. As we saw last season, most teams are only willing to surrender a draft pick for a top of the market player. Santana was not top of the market in a thinner pitching pool last year, even while coming off a better year. His value is lower this year and with a protected draft pick, the Red Sox will not need to be as thrifty in their acquisitions this offseason. Santana likely represents the best of the second tier options and if the Red Sox only plan to sign one ace, he is the best pitcher available not confined to that ace paradigm.

Likely a number two starter in Boston, Santana put up career numbers as a Royal in 2013. Prior to signing a one year deal with Kansas City (yet another prove-it/flyer deal, for those of you picking up on the recurring theme), he had an up and down (recurring themes all around, but this is Ben Cherington’s prototype!) seven seasons to open his career as an Angel. Very much like Clay Buchholz, Santana has spent much of his career pitching very well, or very poorly, but after two strong seasons with KC and Atlanta, there is reason for optimism.

The source of Santana’s recent success has been attributed to his improved ability to mix up his pitches. The one major concern with him for most of his career was his appalling fly ball rate, and concerning lefty-righty splits, but since the successful implementation of a sinker ball as a Royal he has seen his groundball rate make up substantial ground on his flyball rate and his split stats even out as well. If he resumes his fly ball tendencies, his tenure at Fenway Park could be disastrous (see: Jake Peavy) but if he maintains his results, he represents a far better number 2 starter than we currently have on the roster. And if he is forced to once again settle for a below market deal due to draft pick compensation attached to him, Ben Cherington may pounce on the 31-year old righty.

3. Jon Lester

Aug 23, 2014; Oakland, CA, USA; Oakland Athletics starting pitcher

(31) at the end of the top of the fifth inning against the Los Angeles Angels at O.co Coliseum. Mandatory Credit: Kelley L Cox-USA TODAY Sports

Jon Lester is not at the top of my free agent target list. He is a tremendous player who will almost certainly not be worth the money he makes after year four of the contract he will sign. Despite the wishes of all of Red Sox Nation, I see very little chance of a Lester reunion barring a serious hometown discount, particularly on the length side. If he wants to take a five year deal and come back, then I will embrace him with open arms and shed a tear. I don’t see that happening.

As phenomenal as five year $115 million sounds (I might go all the way up to $130 mil on a five year deal…$26 mil per isn’t totally crippling), Lester likely will take the six or seven years he will almost certainly be offered by New York, Chicago, Texas, or Seattle (or all of the above, OR the always lurking mystery team). Lester’s numbers this year speak for themselves: 16-11, 2.46 ERA, 1.10 WHIP, 220 K’s and a shutout. BUT, we need to take into account more than one year when handing out a mega deal.

As much as I hate to play into the chicken and beer “scandal,” Lester was not exactly an ace in 2012, when he finished with a 4.82 ERA. He didn’t even look like an ace for most of 2013, when he finished with a 3.75 ERA, and people seem to forget just how bad he was most of last year. Buchholz was Boston’s ace last year, even if he missed time, and just like Lester did, he could very easily bounce back next year. Lester would be a great player to have next year. But I don’t believe we can say the same about 2019 and beyond and I think Ben Cherington feels similarly.

1. James Shields

Sep 5, 2014; Bronx, NY, USA; Kansas City Royals starting pitcher

(33) pitches against the New York Yankees during the first inning of a game at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports

This one is quickly moving towards “too obvious not to happen” territory, but an interesting wrinkle has been added to the story thread as James Shields leads the upstart Kansas City Royals into a postseason series for the first time since 1985.  I could get caught up in that narrative, but instead, I turn my gaze to the fate of my own team, and with their 2014 season over, it is high time to look to 2015.

In my last piece, I outlined a rotation highlighted by Clay Buchholz as a number two starter, and Joe Kelly, Allen Webster, and Rubby De La Rosa comprising the back three. Now, I also pointed out that even De La Rosa’s spot is a tentative one, winning more by default than by performance. Whether or not De La Rosa is the eventual number five starter, this team needs an ace. And Shields looks to be the man for the job. Over the last four seasons, the 32-year old right hander has never allowed his ERA to surpass 3.52. According to FanGraphs, Shields has pitched to a 16.5 WAR over these last four seasons; this number is a mere .6 behind the number Jon Lester has compiled, 17.1, but despite this fractional difference in player value, don’t expect decimal points to divide these two in terms of contact numbers.

This article by Mark Vandeusen of B/R offers an in-depth look at type of contract Shields will end up with this winter. I would forecast a similar range in both years and dollars, and barring some truly wild bidding, expect him to land in the range of three to five years and $75-$110 million. Three years seems overly optimistic, but I would not be shocked to see Shields wind up with a deal consisting of four years and $90 million, or five years and $100 million. It would be shocking to see anyone go north of five years and $110 million, and I honestly don’t see that pricing the Sox out. Shields is the free agent I want this winter, and I think there is a good chance that the Sox will go out and get him.