2015 Boston Red Sox Armchair GM series: John’s take


“Redundancy” is the word I’d use to describe much of the current state of the organization. Having not played the role of buyer in a blockbuster since acquiring Adrian Gonzalez, the Red Sox have since had four drafts (not counting the draftees from 2010 – many of those signees hadn’t even made a professional debut, let alone played a full season for an affiliate). The farm is the deepest it’s ever been. There are now two young catchers who are projected to be long-term solutions behind the plate. There are also three left-handed pitching prospects who are knocking on the door.The combination of an emerging phenom, two deadline acquisitions, an in-season international signing, and returning incumbents have created an outfield logjam (more so at the corner spots than in center).

With all the redundancy, it’s hard not  to see this club pursuing at least one trade in the offseason. Even with a relatively large group of departing free agents and non-tenders, those vacancies will quickly be filled.

Sep 22, 2014; Bronx, NY, USA; New York Yankees third baseman

Chase Headley

(12) rounds the bases in front of Baltimore Orioles shortstop

J.J. Hardy

(2) after hitting a solo home run during the eighth inning at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports

Departing Free Agents/Non-Tenders

Burke Badenhop – Eligible for free agency.

Craig Breslow – Decline his $4 million option, give him his $100,000 buyout, thank him for 2013, wish him a good rebound wherever he winds up next season.

Koji Uehara – Eligible for free agency.

David Ross – Eligible for free agency.

Ryan Lavarnway – Non-tender. He’s out of options and has no future in the organization as anything other than organizational depth. He probably signs with another team on a Minor League deal.

Jonathan Herrera – Non-tender.

Carlos Rivero – Non-tender.

Jemile Weeks – Non-tender.

40 Man Roster Additions

Blake Swihart– The top prospect in the organization. Only way he’s leaving the organization is in a deal for a middle of the order slugger or (maybe) Chris Sale.

Eduardo Rodriguez– The LHP prospect they got for Andrew Miller. He pitched like an ace down the stretch for Portland and Pawtucket and could very well have a future as a top or middle of the rotation starter.

Sean Coyle
– A second baseman by trade, Coyle is essentially roadblocked for the foreseeable future with the presence of Dustin Pedroia. However, like Mookie Betts, he began expanding his versatility this past season by playing some of his games at third base. He showed a strong arm and good footwork while learning a new position. He’s shown solid power potential and decent OBP skills during his development (the high OBP is due more to hitting for a solid average as his walk totals haven’t been overwhelmingly high).

Coyle may or may not have a future with the Red Sox. However, he is a solid prospect who has a chance to make the big leagues, though it remains to be seen if it’s as a starter or reserve. Given the depth of the farm system, Coyle would probably be ranked higher in many other organizations. He’ll be added to the 40 Man if he isn’t dealt in a trade.

Travis Shaw– While he collectively put up an .826 OPS with 21 homers between Pawtucket and Portland, Shaw is probably not the first baseman of the future. There are concerns about his bat speed, and the significant drop in OPS from Double A to Triple A (.954 to .752) did nothing to lessen those concerns.

That being said, he could provide a solid insurance policy should the need arise. At the very least, he provides extra depth at the corner infield spots and designated hitter. If he gets a chance and puts up really good numbers, he could be a very good “sell high” candidate.

Luis Diaz– The righty was actually Rule 5 eligible last season, but was eligible to be protected from the Double A part of the draft due to still being in Single A. That won’t be the case this season. Between Salem and Portland, Diaz put up a 3.54 ERA, 1.283 WHIP and 111/44 K/BB in 145 innings. He’s not an elite pitching prospect, but will likely be scooped up if not protected from the Rule 5 draft. With the depth of pitching ahead of him, Diaz’s future is likely as a reliever or a trade chip. If he’s the latter, it’s better to get something in return rather than nothing. Hence why he’ll have a spot on the 40 Man roster this offseason.

Noe Ramirez– A fourth round pick in 2011, Ramirez has been a consistent strike thrower during his development and should have a future in the Boston bullpen. This past season at Double A Portland, Ramirez recorded 18 saves with a 2.14 ERA, 1.069 WHIP, and 56/16 K/BB in 67 1/3 innings. Relievers tend to be a popular commodity in the Rule 5 draft, so it would be wise to add Ramirez to the 40 Man Roster. He’ll likely begin the year in the Pawtucket bullpen. If he continues the success he’s had to date, he’ll be in the Boston bullpen at some point in 2015.

Starting Pitching

The Red Sox had a mass exodus of starting pitching during the 2014 season. Felix Doubront scuffled out of the gate but felt entitled to a spot in the rotation. He was dealt to the Cubs. If he wasn’t getting hit hard, Jake Peavy was pitching effectively but a victim of poor run support. He won only one game before being dealt to the Giants. John Lackey pitched effectively and netted an intriguing return of Joe Kelly and Allen Craig. Jon Lester did what he usually does before being dealt to Oakland.

It’s likely the club will need to acquire at least two, maybe even three starting pitchers this offseason. One of the acquisitions should be a top of the rotation type and the other one or two should be an effective and/or durable innings-eater.

Plan A: Ace

For me the number one target has to be Jon Lester. He has no draft pick compensation attached, there’s the familiarity factor, and I like the chances of him remaining durable and effective as he ages. I would present two different offers: Five years $140 million with a $20 million option for 2020 or six years $150 million with a $15 million option for 2021.

If Lester accepts a different deal elsewhere, they should avoid signing either of Max Scherzer or James Shields. The former will be every bit as costly as Lester, but has draft pick compensation attached and I also have concerns about his long-term durability. The latter is not a big game pitcher despite his moniker, and could also have long-term durability concerns.

The best route to go down if unable to sign Lester would be to pursue a trade for Cole Hamels or Jeff Samardzija. I wouldn’t part with Mookie Betts or Blake Swihart for either. However, I would part with Henry Owens or Eduardo Rodriguez as well as any of our young right-handers, one of our emerging low Minors studs (Manuel Margot or Rafael Devers), Sean Coyle, and a throw-in or two. It’s more than fair when considering the amount of money still owed to Hamels and only one season left on Samardzija’s deal.

Of course, the A’s or Phillies may not agree with that sentiment and could decline to settle for anything less than Betts and/or Swihart. If that’s the case, ponying up for Lester makes the most sense.

Plan B: Rest Of The Rotation

The free agent market for mid-tier starters is an intriguing one. If Ervin Santana hits the market without receiving a qualifying offer, he will likely have many suitors. My guess is he is extended a qualifying offer and accepts. Like Kendrys Morales and Stephen Drew last season, it’s not wise to be a mid-tier free agent with draft pick compensation attached.

Two more likely targets are Justin Masterson and/or Brandon McCarthy. Masterson struggled in 2013 and will be likely be looking to reestablish his value on a one-year deal. While he’s had some inconsistencies, he’s also been pretty durable and there is familiarity between the pitcher and the Red Sox.

McCarthy finally delivered his first 200 inning season and was pretty effective after being acquired by the Yankees. He’s more likely to get a deal for two or three years but at a lower annual salary. I’m actually all for signing them both.

Third Base

In 2013, the Red Sox were able to win a World Series in spite of having subpar production at the hot corner (though Xander Bogaerts emerged as a crucial wild card at just

Sep 6, 2014; Miami, FL, USA; Miami Marlins right fielder

Giancarlo Stanton

(27) in the dugout of a game against the Atlanta Braves at Marlins Ballpark. The Brave won 4-3. Mandatory Credit: Robert Mayer-USA TODAY Sports

the right time). This past season, not solidifying the position was one of many flaws on a team that would finish in the AL East cellar. Will Middlebrooks has no business beginning next season on the big club if he isn’t dealt in the offseason. Garin Cecchini hit well down the stretch and made some nice plays, but he may need another season of development. He still could have a future in Boston, but it might be in the outfield rather than at third base.

The answer for third base in 2015 will come from outside the organization. It would be wise to snag a particular free agent as soon as possible. This free agent is Chase Headley. I previously mentioned how I thought Headley would be an excellent fit in Boston. He won’t be all that expensive and comes without draft pick compensation. He’s also an excellent fielder. Sandwiching Xander Bogaerts between two elite defenders would be a very wise move.

Pablo Sandoval is another “Buyer Beware” for me. He is an excellent hitter and probably won’t land a deal that’s in the Fielder/Howard level. But even a four or five-year deal for a player with that body type can be a huge risk. He’s unlikely to remain at third base and his OBP tends to fluctuate too much to where his bat isn’t playable at first. The best long-term position for him would be at designated hitter. But with David Ortiz potentially being on board for another three seasons, it’s best to stay away. Even more so considering he’ll have draft pick compensation attached.

There are a couple of decent trade targets like Luis Valbuena of the Cubs and Lonnie Chisenhall of the Indians. I have no interest whatsoever in Pedro Alvarez and I highly doubt the A’s will trade Josh Donaldson, who they have four more years of control over. Valbuena and Chisenhall may or may not require an overwhelming return, but with a solid investment on the free agent market in Headley, they’d be better off retaining the prospects for a bigger fish (yes the pun is totally intended).

I put the acquisition of Headley up there right after the acquisition of a number one starter. Get him signed and get it done quickly.

Backup Catcher

Another one-year deal for David Ross makes sense on the surface. He’s still a good defensive catcher and would be a great mentor for Christian Vazquez and Blake Swihart. But he’s also going to be 38 and isn’t likely to improve with the bat. It wouldn’t surprise me if Ross’ contributing to ESPN during the 2014 post season was just the beginning of his post-playing career and that he’s played his last game.

There are a couple of intriguing names on the free agent market. Gerald Laird is every bit as good a fielder and is two years younger. It should be noted that Laird’s offense regressed significantly in 2014. Perhaps a move to a more hitter-friendly home ballpark could reverse that trend.

Ryan Doumit is another potential free agent target. He’s never been regarded as a good defensive catcher and only played two games behind the plate last season. But he is versatile and can also play corner outfield and first base. He had a terrible season offensively in 2014. But maybe a move to Fenway and the tutelage of Chili Davis can get him back on track.

John Jaso is a potential trade target. He’s a solid hitter who bats from the left side. Defensively, he’s not Christian Vazquez, but is adequate enough to handle the job. Maybe he can be included in a deal with Jeff Samardzija

If unable to acquire a backup through a trade or free agent signing, Dan Butler could provide a decent internal solution as a backup, though that’s unlikely to happen.


This figures to be an area where things get worked out from within. Rubby DeLaRosa and Brandon Workman are likely candidates to shift to relief on a full-time basis. With an underwhelming market of left-handed relievers (at least the ones not named Andrew Miller), the Red Sox might be better off giving a bullpen spot to Edwin Escobar rather than pursuing a trade for a lefty reliever.

Steven Wright
might be a candidate for the fifth starter spot, and possibly Junichi Tazawa if the Red Sox oblige his wish to make him a starter again. At least one will likely have a spot in the pen, if not both.

The closer’s role is really the only area of need. I would only bring Koji Uehara back for the same salary he’s made in each of the past two seasons. Perhaps he’d hold down the post for one more season as they groom one of the young arms as the long-term solution beyond 2015 (the Wetteland-Rivera model). Or maybe the Red Sox reunite with Andrew Miller and hand him the closer’s role.

Building a bullpen isn’t an exact science, but it would be encouraging to have the bulk of the solutions come from within rather than giving a seven-figure salary to a free agent.

Address Some Of The Redundancy

As of right now, left field and right field are going to be very crowded in 2015. Daniel Nava and Allen Craig will likely be used as reserves despite being starters for the better part of their careers. But the former is still a very affordable asset and the other is an untradeable unknown. That leaves four players competing for three spots: Rusney Castillo, Yoenis Cespedes, Mookie Betts, and Shane Victorino.

Castillo wasn’t signed to a $72 million dollar contract if he wasn’t intended to begin the season as a starter. He will be in the opening day lineup. It’s just a matter of whether he’s in center field or right field and whether he’s batting leadoff or seventh.

Betts is only getting dealt in a blockbuster for a certain corner outfielder. End of story. Moving on.

Yoenis Cespedes is fun to watch, but he is also flawed. The recent reports of him being unwilling to play right field (where his cannon arm wouldn’t go to waste) and improve his defense can’t be pleasing. His plate approach doesn’t live up to the organizational philosophy as his OBP is very below average. He does hit for above average power, but the home run totals will be in the 25-30 range rather than 40+ as some pundits might claim. That being said, he is a solid source of right-handed power.

Unless the club acquires a different power-hitting outfielder (and no I don’t think Cespedes will be a chip in said deal) and/or if he can net an above average starting pitcher in return, I look for Cespedes to play the last year of his deal in Boston. Then I look for him to hit the free agent market and sign elsewhere.

That brings us to Victorino. It’s doubtful he’ll perform at his 2013 level. It might be more doubtful to think he’ll be content as a reserve outfielder. There probably isn’t a team out there willing to take the entirety of his remaining $13 million owed, but if the Red Sox can eat up to half of it, there should be a suitor. Find a trade partner and free up a few million to reallocate elsewhere.

Not that I’ve addressed the outfield, let’s get to Clay Buchholz. I’m sick of his act. He’ll never remain healthy for a whole season or pitch consistently. I don’t care what the return is. Just eat half of his 2015 salary and let him be somebody else’s problem.

There’s one more move I’d try to make. It’s no guarantee, but definitely worth trying…

Make A Trade Proposal For Giancarlo Stanton

While the Marlins have been unwilling to move him to this point, there’s also concern for potential suitors given what happened to him late in the season. But I’m confident he’ll rebound.

The Marlins are adamant about not dealing him and supposedly want to extend him. But it’ll take a lot of money to convince Stanton to stay put. They’ll also have to spend more money to give him a more fitting supporting cast. Both are against the business philosophy of the Marlins, and I’ll be surprised to see it happen.

This brings us to a trade proposal. For Stanton I would offer: LHP Henry Owens or LHP Eduardo Rodriguez, C Blake Swihart, 2B/OF Mookie Betts, one of RHPs Allen Webster/Anthony Ranaudo/Matt Barnes, one of 3B Rafael Devers or OF Manuel Margot, and one or two throw-ins such as OF Jackie Bradley and/or 3B Will Middlebrooks.

So the Marlins would be getting a potential All Star Catcher, a potential top of the rotation lefty, a serviceable right-hander, an exciting game-changer in Betts, a high-reward lottery ticket in Margot or Devers, and maybe Middlebrooks or Bradley turn it around with a change of scenery. It’s a very good haul for an excellent player. Probably one of the best offers the Marlins will get at this time.

If the Marlins agree, I’d begin negotiating an extension. Eight years and $250 million or ten years and $275 million is a good start. Is it a pricey investment? Yes. But we’re talking about a guy who would dent the Citgo sign, let alone the Green Monster.

And if they don’t, there’s always next year (or the July 31st trade deadline…)

Let’s Review

Add the previously mentioned seven prospects to the 40 Man Roster, acquire an ace, protect that draft pick, sign Headley, sign one or two other solid starters, don’t overpay for a free agent reliever, trade Victorino and Buchholz, and make a pitch for Stanton.