Home Baseball Sunday Column: Just What Can the Red Sox Do About Their Rotation?

It’s an interesting dilemma.

Having shipped off four of five members of their Opening Day rotation in less than a month, the Boston Red Sox are in a unique position heading into the offseason.

Clay Buchholz is the lone survivor, and he surely does not have the embodiment of an ace. Young Joe Kelly was also brought in via trade, and would likely settle into the No. 2 role in 2015 if the rotation is not addressed.

As far as 2014 goes, however, it’s a youth movement. And the prospects—Allen Webster, Rubby De La Rosa, Brandon Workman, Anthony Ranaudo, Matt Barnes, Henry Owens and others—are all looking to prove something.

But what about 2015? There’s almost no fathomable scenario in which Buchholz makes the Opening Day start … right?

There are alternative options out there. And, supposedly, Boston has the money to embark on the free agent market. However, there isn’t much out there suitable for the Red Sox and their philosophy of not doling out five-plus year contracts to 30-year-old pitchers.

That means Max Scherzer is likely out of the question, as he turned down a six-year extension from the Detroit Tigers already. Of course, there’s always a chance the Sox could break that mold of thinking, and if they did, the recipient would likely be Jon Lester, whom the team traded last Thursday and is set to become a free agent this fall.

They may be in on pending free agent Edinson Volquez, a current starter for the Pittsburgh Pirates. Justin Masterson, Ryan Vogelsong and James Shields are also possibilities on the market, but none of them profile as frontline starters going forward (although almost all would be a favorable option over Buchholz).

If they were to go in a different route, Red Sox general manager Ben Cherington has put his club in a good position to solve the problem by trade.

Cole Hamels was claimed by the Chicago Cubs last week, but not traded.

Hamels was claimed by the Cubs last week, but not traded.

The first name that comes to mind is Cole Hamels, a high-salary player signed through 2018 (team option for 2019) with the Philadelphia Phillies. Rumored to move at last week’s deadline, multiple reports suggested the team was seeking three upper-echelon prospects in return for the to-be 30-year-old. That’s a big reason he didn’t move.

To be fair, it’s a bill the Red Sox would have no trouble paying from a stacked farm system. But if a team has to dole out the farm for this guy, there’s a chance the Red Sox could do better than an aging veteran (yes, 30 is “aging” now), a type of player the front office has made clear they don’t take a liking to.

Hamels is a great pitcher, but I can’t quite gauge the thinking of selling off prospects for a Jon Lester knockoff.

After the Phillies’ lefty, options are somewhat limited trade-wise, but it would make sense for the Sox to hunt talent from a below-average, somewhat non-contending team.

To do this, we have to think outside the box a little bit. Two possibilities could be Chris Sale of the Chicago White Sox and Yu Darvish of the Texas Rangers, both elite pitchers in the American League who would unquestionably be arduous to acquire.

Sale, 25, is signed through 2019 with two team options in 2018 and 2019. He is widely regarded as one of the best left-handed pitchers in baseball; it would be extremely tough to pry him from the South Side.

But with the Red Sox’ bevy of prospects, Cherington could potentially entice Chicago to deal its ace. It doesn’t seem likely, but if the Red Sox are unable to resign Lester, they may be desperate enough to dangle a large package for Sale.

For Darvish, 27, it’s only his third year in the league since coming over from Japan. He is signed through 2017 for modest money ($10.25 million AAV) and is regarded as one of the most elite power pitchers in baseball, as he was first in MLB in strikeouts last season.

It may be easier to acquire Darvish than Sale, partially because of age and state of the Rangers’ franchise (worst record in baseball in 2014). Sale would likely yield the larger return to the suitor, and that’s expected since Sale seems to have a higher ceiling.

If Sale’s price is too high, the guess here is that if the Red Sox were to overwhelm the Rangers with a (still large) package of juicy prospects—which, by all means, they can do—Texas may be inclined to move Darvish.

However, like I said, neither of these deals would be easy to complete. I want to reiterate that.

But what exactly would it take to bring either Sale or Darvish to Boston? Well, a lot. But let’s explore some (possibly) realistic options.


Potential Chris Sale trade scenario 

Red Sox acquire:

  • LHP Chris Sale
  • Cash considerations

White Sox acquire:

  • 2B/OF Mookie Betts
  • LHP Henry Owens
  • C Blake Swihart
  • RHP Allen Webster
  • LHP Edwin Escobar
  • Competitive Balance (B) Pick

For me, this is a tough transaction to draw up because Sale’s worth is ridiculously high. In this deal, Chicago would get two major league-ready players in Mookie Betts and Webster. Owens is Boston’s top pitching prospect who has dominated the minor leagues, and the White Sox would likely require the return of a potential ace in this deal. Blake Swihart is a guy the Red Sox absolutely love and would hate to part with, but I think he would be a make-or-break in this deal as well. However, I think the recent play of catcher Christian Vazquez could possibly lighten the blow from parting with a guy like Swihart. Edwin Escobar is one of the two pitchers Boston acquired in the Jake Peavy deal, and is currently starting with Triple-A Pawtucket. The draft pick they received in the Lester deal could also be a factor in negotiations.

Still, it would be tough for the White Sox to part ways with Sale, even with this exorbitant return. However, this is a possible return that could satisfy Chicago. It would also save the White Sox from paying the starter’s $53.2 million collective salary through 2019 (with options).

It’s also a strong possibility—and probably a smarter option for Chicago—the White Sox try to package John Danks and his large salary to collect more prospects and unload more payroll.

That could look something like this.


Potential Chris Sale + John Danks trade scenario

Red Sox acquire:

  • LHP Chris Sale
  • LHP John Danks
  • Cash considerations

White Sox acquire:

  • RHP Rubby De La Rosa
  • 2B/OF Mookie Betts
  • LHP Henry Owens
  • C Blake Swihart
  • RHP Allen Webster
  • OF Manuel Margot
  • RHP Matt Barnes
  • Competitive Balance (B) Pick

It’s a pretty similar trade, except De La Rosa sweetens the pot as an MLB-proven hurler, and Barnes, a former first-round pick, has been added in—as well as Manuel Margot, a 19-year-old Dominican product who would fill somewhat of a shallow outfield in the White Sox’ organization.  This would be a huge salary dump for the White Sox with an enormous return.

The biggest reason the price is so high for both is multiple years of service time left on each player’s contract.

Now, as for Darvish …


Potential Yu Darvish trade scenario

Red Sox acquire:

  • RHP Yu Darvish

Rangers acquire:

  • 2B/OF Mookie Betts
  • RHP Allen Webster
  • LHP Edwin Escobar
  • SS Deven Marrero
  • RHP Matt Barnes
  • OF Bryce Brentz
  • PTBNL (a pitcher)
Mookie Betts appears to be someone the Red Sox could trade.

Mookie Betts appears to be someone the Red Sox could trade.

The biggest need for the Rangers is major-league ready starting pitching depth, and with Webster, Escobar and Barnes, they can very quickly plug them in with returning (and hopefully healthy) MLB-proven starters. As far as Betts, Deven Marrero and Bryce Brentz go, they represent offensive talent that’s either immediately applicable at the MLB level, or very close to it (Marrero and Brentz being the latter). Marrero could represent some depth at the shortstop position behind current starter Elvis Andrus (recently drafted Ti’Quan Forbes is a long way away).

Again, this deal would be tough for Texas, but given their current situation and developing prospects, it may be wise for them to add a big package and focus on 2016 and 2017, when the likes of Joey Gallo, Jorge Alfaro and others can be plugged into the core.

Look, I’m no general manager. I have no idea how to negotiate player trades like actual executives have to. This is merely a rough idea of what I think it would take to acquire either of these players. I’d love to hear your feedback on these proposed deals.

Of course, reports are still swirling that the Red Sox will package these young players to acquire Miami Marlins’ outfielder Giancarlo Stanton, the most recent coming from Jon Heyman of CBS Sports on a radio appearance. And while it would be a huge boost to the team, there are more pressing issues for the Sox than corner outfield—which Boston just addressed in adding both Allen Craig and Yoenis Cespedes at the deadline, not to mention having Shane Victorino returning from back surgery next season. On top of that, there is still Daniel Nava, Brock Holt and numerous other options.

They don’t need Stanton. They need a No. 1 starter.

The point is Sale and Darvish are both elite pitchers, and if the Red Sox fail to sign a Lester or a Scherzer, they will be lacking that reliable No. 1 guy. And, retrospectively, what would be the point of dealing Lester for Cespedes (can opt out after 2015) if the Red Sox aren’t planning on winning with him next season?

The motive of the Red Sox’ trades last week seemed to translate to contending immediately in 2015. And they took a big step forward in solidifying a struggling offense in adding Craig and Cespedes. But what’s the point of it all if there’s no one to anchor the rotation?

Trading for Stanton would require either Owens or Xander Bogaerts be included in the deal. You would likely need those guys expendable to acquire the pitching you need.

What’s the point of selling the farm for Stanton if Buchholz is the ace?

Even if the Red Sox were to sign a James Shields in free agency, a rotation of Shields-Buchholz-Kelly-De La Rosa-Webster is not about to win anything.

And even if they are to bring Lester back, a rotation of Lester-Buchholz-Kelly-De La Rosa-Webster is still in no position to win.

The Red Sox should proceed on one of these proposed trades whether or not Lester re-signs. And if he doesn’t return, Boston should scoop up Shields and then make a trade for Sale (and/or Danks), or Darvish.

The Red Sox are already set to become the first team to go worst-to-first-to-worst. If the Red Sox really want to convince their fans they can be the first team to ever go worst-to-first-to-worst-to-first, the Opening Day rotation should be:

  1. Chris Sale, LHP
  2. James Shields, RHP/Edinson Volquez, RHP
  3. John Danks, LHP
  4. Joe Kelly, RHP
  5. Clay Buchholz, RHP/Brandon Workman, RHP/Anthony Ranaudo, RHP

If not that, it had better be legitimately equivalent.

I’ll tell you one thing: You won’t be winning many regular season or playoff series otherwise.

It is absolutely realistic. They have the ammunition to get it done.

Especially if their provincial philosophy prevents them from paying Lester or Scherzer, proceeding in one of these trade options becomes a must. The Red Sox should be motivated to use their extremely deep prospect system to remedy the issue. Get it done.

They have money. They have prospects. They can trade for the A-list superstar, and afford to pay him.


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