Boston Red Sox: What restrictions on finding an ace?

Oct 3, 2015; Los Angeles, CA, USA; Los Angeles Dodgers starting pitcher

Zack Greinke

(21) in the first inning of the game against the San Diego Padres at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-USA TODAY Sports

1) The Draft Pick

Ah, the MLB draft, justifying abject failure since way back, the eternal assumed modus operandi of teams who are so bad they could only be tanking on purpose. The draft, ordered such that, depending on how bad your team’s record was in the year, will ultimately decide their order of choice for each prospect, from worst to best. Unfortunately for the Red Sox, sticking your head out of the sands of failure to the desert of mediocrity doesn’t provide the same kind of benefits.

You see, Boston had another disappointing season, it’s true. A turnabout in fortunes in the second half, spurred on by resurgent performances from old hands like David Ortiz and Dustin Pedroia, and kicked into high gear by blossoming youngsters like Mookie Betts, Xander Bogaerts and Eduardo Rodriguez, saw the Red Sox manage to pull back to only 12th worst in baseball. 12th worst in baseball, 12th pick in the 2016 draft.

Now, for players who are considered “free agents”, if they have stayed with their current club for the entire season before free agency, they are eligible to receive a “qualifying offer”. The club they leave offers them a year contract at a set amount, which they inevitably turn down. The upshot of this is that if another team successfully signs said player, they lose their first round pick in the following year’s. That escalated quickly.

There are some protections, known as “protected draft picks” reserved for teams who are so pitifully bad that they honestly need all the help they can get. Why aren’t the Red Sox in this category? Well unfortunately, this year at least, only the first 11 draft picks are protected and, of course, Boston has number 12.

The net result is that it provides a pretty solid deterrent from signing a free agent who has been extended a qualifying offer. The Red Sox’ 12th pick is quite valuable, no club in the history of the draft has ever surrendered a slot that high for any player. On top of that, 2016 promises to have an exciting draft, headlined by a plethora of lightning-armed wunderkind college pitchers, that has me drooling on the keyboard as I type this.

That’s not to say the Red Sox will be dissuaded entirely, but I personally believe that it’s very unlikely that they will sacrifice their pick. Fortunately for Boston, two of the biggest free agent aces this offseason, David Price and Johnny Cueto, are not eligible for qualifying offers and can be had without losing the draft slot.

One pitcher exists that may be worth making the sacrifice for, that is Zack Greinke. Greinke is among the best pitchers in baseball and shows no signs of letting up, indeed he’s getting better, at 32 years old. Aside from Greinke, who we will discuss more later, there’s probably not going to be anybody Dombrowski values enough. Jordan Zimmerman hasn’t shown he is consistently able to be an ace, indeed he didn’t even command the #2 slot for the Washington Nationals, and with the resources available, the Red Sox can do so much better without the risk of missing out on a prize in the 2016 draft.

Next: Do they fit in Boston?

Sep 11, 2015; Bronx, NY, USA; Toronto Blue Jays starting pitcher David Price (14) pitches against the New York Yankees during the second inning at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports

2) Do they “fit” in Boston?

The ace is more than just the best hurler on the staff, they are the face of the franchise, the foundation upon which the rotation is built for years, the seller of much merchandise. When things are going bad the ace suffers much scrutiny, when things are going good the very same. Everything is under a microscope and the win button is permanently pushed. The pressure is enormous.

Bottom line, to be top of the rotation you need to fit at Fenway. I could see this becoming a potential stumbling block for some of the top choices available.

David Price has a somewhat strained history with the Red Sox and certainly with David Ortiz. A rivalry blossomed with one Big Papi bat flat in 2012 that resulted in Price plunking Ortiz and Mike Carp on May 30, 2014. Price so infrequently hits batters with pitches that its chance of being accidental has the same percentage as the number of batters you and I plunked this year.

Speaking on Red Sox Hot Stove chat, WEEI’s Rob Bradford said the following:

“I like Price. I think his delivery translates into a healthy 30’s. But I have a hard time believing he will make his home here.”

Bradford also quotes from a rather awkward interview earlier in the year between Price and colleague at WEEI John Tomase. Nothing seemingly ruled out, but I concur with Bradford that it’s difficult imagining Price taking the mound in Boston, which could be thousands of miles outside his comfort zone.

Then there’s Greinke, whose stunning 1.66 ERA and reliever-beating 0.84 WHIP are the best in baseball. He’s just fresh off of a regular season with 19 wins, 3 losses and an amazing 222 innings pitched. Greinke would and should, you’d imagine, be at the top of the list to be the top of his rotation. Not so, as the Boston Herald’s Scott Lauber writes, Greinke nearly quit baseball in 2006 after being diagnosed with social anxiety disorder on top of clinical depression.

Greinke “definitely wouldn’t want any more stress or additional media attention,” one source close to the pitcher told Lauber.

Well, that’s that then. See, the media in Boston isn’t exactly unknown for scrutiny, exhibit A – Pablo Sandoval. Sandoval was answering nature’s call on the great white telephone during a game, meanwhile using his actual telephone to show approval of photos on Instagram. Just such an event caused a media fury and ended, somewhat ironically, with him doing a lot more sitting as he was benched for the Red Sox next game. This time, without the phone of course.

Greinke would perhaps struggle with the pressure of being the sole leader in Boston. Ultimately the situation in his current club, the LA Dodgers, is more comfortable for him as he is able to sit behind Clayton Kershaw and avoid the stresses of being the sole No. 1 starter.

In the end, I expect that Dombrowski will chase both Price and Greinke to the limits. Both are among the best pitchers in baseball today and are so obviously the best choices available that it would be folly not to try. Just don’t be too surprised if you don’t see them wearing a B cap next year for reasons other than money.

Next: John Henry

Sep 8, 2015; Oakland, CA, USA; Oakland Athletics starting pitcher

Sonny Gray

(54) throws a pitch against the Houston Astros during the first inning at O.co Coliseum. Mandatory Credit: Ed Szczepanski-USA TODAY Sports

3) John Henry

The Red Sox principal owner has gone on record stating his preference for young pitchers on long (and affordable) team controlled contracts. While Dombrowski wasn’t brought in to be restrained, that doesn’t mean that this dynamic has gone away.

If anything, previous Red Sox General Manager Ben Cherington was known for being stingy with prospects and splurging on free agents to protect the farm. With Dombrowski, all cards are on the table and all options to success will be explored. Speaking to WEEI, Dombrowski had this to say;

“I have always tried not to say players are untouchable. The reason I have done that is because you can never tell when somebody makes you an offer you just can’t believe. If you have Miguel Cabrera, somebody may offer you two Miguel Cabreras. Probably not going to happen, probably never will happen, but unless you listen, you don’t know.”

First, two Cabreras would be bizarre but incredible. Second, it’s clear that Dombrowski is willing to listen on anybody, to get what he needs. With this in mind, he has a lot of trade chips ready and waiting for use if the price is right. An ace on a controllable contract who is still in his mid-twenties can carry the side for years and free up potential finance in the payroll for other upgrades, as required.

There are certainly several tempting potentials. Rumors have been flying around about a possible trade for Oakland A’s ace Sonny Gray who is only 25 years old and has a career ERA of 2.88. Such a pickup would be costly, but the rewards for Boston are about as big as they come.

Another option could be ace-in-the-making Carlos Carrasco, currently in waiting for Dombrowski’s call at the Cleveland Indians. Carrasco’s 3.36 ERA may not be as flashy as Gray’s 2.73 on the year, but he managed a top ten FIP of 2.66 and has an obscene K/9 rate of 10.5. While a little older than Gray at 28, he’s still young and the Indians could provide an easier trade partner. Their solid pitching staff is lacking in big bats and the Red Sox could dangle a number of show-ready players like Blake Swihart and Jackie Bradley Jr in a package with some prospects. They could even elect to take Hanley Ramirez off our hands. We wish.

Speaking of Ramirez, the San Diego Padres could provide a suitable dumping ground for his and other ill-advised free agency contracts that Boston took upon themselves last offseason. Provided the Red Sox eat some of the money of course. In return, there is an enticing piece in Tyson Ross available who, at 28, is pitching like an ace with an ERA of 3.26 and K/9 of 9.7.

All of these options and more may be appealing to Henry and certainly aren’t outside the realms of possibility for Dombrowski. Conversely, options like Johnny Cueto could be easily ruled out due to long standing concerns for his arm that have only been compounded by more recent disappointing outings.

Whatever the result, Dombrowski has his work cut out for him and doubtless won’t be putting all his baseballs in one bag. All of the options will be examined and many tires will be kicked in what proves to be one of the most exciting offseasons in Boston in some time.