Red Sox trade targets: High priced starting pitchers

The more time I spend trying to figure out the inner workings of a general manager, the more I realize how fruitless of a task this is. Anyone tasked with trying to mock a Bill Belichick draft pick or predict a Patriots free agent signing can fathom this.

Ben Cherington is another fantastic example of this, he made his first splash as general manager of the Red Sox by orchestrating quite possibly the largest trade in MLB history. He sent Adrian Gonzalez, Carl Crawford and Josh Beckett to Los Angeles in a cap slashing move that left many scratching their heads. The big money Red Sox were effectively “folding their hand” and conceding defeat; a first for the John Henry-Tom Warner-Larry Lucchino trio.

what if a Josh Beckett type deal comes along, where a pitcher thought to be unavailable is suddenly in play if Mookie Betts or Xander Bogaerts are included?

He followed that up with a series of very “un-Red Sox-like” signings bringing in Shane Victorino, Ryan Dempster, Mike Napoli, Koji Uehara, David Ross and Jonny Gomes. Cherington seemingly had chosen quantity over quality, as none of the contracts exceeded $39 million. As we saw, those all ended up being quality signings (except perhaps Dempster) and culminated in the 3rd World Series trophy in a decade being hoisted in Boston.

Naturally, he did the same thing the following offseason… to very poor results. The Red Sox quickly bottomed out in an AL East that was not even as competitive as years past. Cherington hit the eject button on 2014, trading away star pitchers Jon Lester, John Lackey and Andrew Miller, but quickly began rebuilding for 2015. He called up top prospects Mookie Betts and Christian Vasquez and inked Rusney Castillo to a $72 million contract that seemed much more “Red Sox-like”, alongside star deadline acquisitions Allen Craig and Yoenis Cespedes.

And now the rumors are that Allen Craig and Yoenis Cespedes could already be on their way out of Boston, and Jon Lester could be coming back to Boston alongside the newly acquired Hanley Ramirez and Pablo Sandoval, and their $88 million, and $95 million respective contracts. Cherington at some point seems to have decided that building through expensive free agents is an unavoidable facet to winning baseball games despite the recent successes of teams like the Ray’s and A’s.

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But the one thing we have not seen him do is trade away his top prospects. And my immediate reaction to the Sandoval/Ramirez signings was that he shouldn’t. My thought process was that as long as he held onto young stars, he could mitigate the risk inherent in these risky free agent signings. But this team needs a number two pitcher. I am still of the opinion that the best way to do this is by using assets not named Xander Bogaerts, or Mookie Betts. But what if a Josh Beckett type deal comes along, where a pitcher thought to be unavailable is suddenly in play if Mookie Betts or Xander Bogaerts are included?

The following seven players are by all indications unavailable. But, with the value of players like Xander Bogaerts and Mookie Betts, maybe these teams could be swayed.

Sonny Gray

Sep 2, 2014; Oakland, CA, USA; Oakland Athletics starting pitcher Sonny Gray (54) returns to the dugout after the top of the first inning against the Seattle Mariners at O.co Coliseum. Mandatory Credit: Kelley L Cox-USA TODAY Sports

This very tweet, courtesy of @NEPD_Loyko (another tremendous Twitter follow for all things Boston sports), was my inspiration to look into this topic:

Unlike the newest Blue Jay Josh Donaldson, there are no indications Sonny Gray is available. But Billy Beane is doing a lot of work to reconstruct his roster and has not shied away from making big trades that raise eyebrows in the past. Gray would be an amazing get for the Red Sox.The 25 year old Gray pitched like an ace this past season with a 3.08 ERA in his first full season, pitching almost 220 innings and winning 14 games. He is not even arbitration eligible until 2017 and he will not sniff free agency until 2019.

This combination of success and affordability makes it unlikely the A’s will trade him, but there are a few things that make it possible. The A’s have a lot of young pitching with Jarrod Parker, Tommy Milone, Drew Pomeranz, and Jesse Chavez plus a few solid pitching prospects including former Red Sox (Andrew Baily trade) Raul Alcantara, Dillon Overton, and the recently brought in pitchers from Toronto: Kendall Graveman and Sean Nolin.

Conventional wisdom says they will trade Scott Kazmir or Jeff Samardzija, but with a lineup that was seriously lacking offense after trading away Yoenis Cespedes, it is possible they would be tempted to move their young ace for a package featuring Mookie Betts and Garin Cecchini, maybe throwing in Henry Owens too.

Kevin Gausman

Oct 10, 2014; Baltimore, MD, USA; Baltimore Orioles starting pitcher Kevin Gausman (39) in game one of the 2014 ALCS playoff baseball game at Oriole Park at Camden Yards. Mandatory Credit: Joy R. Absalon-USA TODAY Sports

The name on this risk that undoubtedly carries the greatest risk, is Kevin Gausman. It is also VERY unlikely the Orioles would be willing to trade him, but if they lose out on Nick Markakis and Nelson Cruz then they will be desperate for some offense. Mookie Betts could play OF or 2B for the Orioles depending on how they view Jonathan Schoop, and given the presence of fellow pitching phenoms Hunter Harvey and Dylan Bundy the Orioles may be willing to move Gausman in order to recapture the explosive offense that lead them to the postseason in 2014.

Gausman has fantastic upside, with the ability to power the front of a rotation. In 20 starts in his first season as a full time starter he earned a 3.57 ERA, but the 23 year old was better than that. His FIP was 3.41 and Baltimore’s sometimes shoddy defense did him no favors. Gausman is still risky because he is not proven, but talent evaluators around the league rave about his ability and while he has question marks, he is also the furthest away from free agency (2021) of the names listed here. A straight up swap for Betts wouldn’t get it done, but the inclusion of some of our major league ready right handed pitchers might be enough to strike a deal.

Henderson Alvarez

Sep 1, 2014; Miami, FL, USA; Miami Marlins starting pitcher Henderson Alvarez (37) delivers a pitch during the third inning against the New York Mets at Marlins Ballpark. Mandatory Credit: Steve Mitchell-USA TODAY Sports

I tried with all of my might to think of a conceivable situation that would involve the Marlins trading the 2013 Rookie of the Year Jose Fernandez. There are none. The 22 year old ace has to be seen as untouchable, even after Tommy John, he still looks like the brightest young pitcher in baseball. Miami has a lot of young pitching talent and a need for some offense beside Giancarlo Stanton, but it just seems impossible to acquire Fernandez, but that said, he is one player I would package Xander Bogaerts for.

The next man up is Henderson Alvarez, one of the players acquired from the Blue Jays for Jose Reyes and Mark Buerhle. The 24 year old was also incredibly successful last year, with a 2.65 ERA in his 3rd year as a starter. Alvarez is another risky name but he is notoriously good at inducing ground balls, a good sign for a pitcher at Fenway park. It’s also possible the Marlins decide they like the current state of their 2015 rotation with Fernandez and Alvarez as a 1-2 punch and hold onto both players. They could just as easily trade their pitching prospects for major league bats, and they are already rumored to be interested in Allen Craig.

Matt Harvey

May 13, 2014; Bronx, NY, USA; New York Mets injured starting pitcher Matt Harvey (33) between innings of a game against the New York Yankees at Yankee Stadium. The Mets defeated the Yankees 12-7. Mandatory Credit: Brad Penner-USA TODAY Sports

Along with Jose Fernandez, Matt Harvey represents one of baseball’s brightest young pitchers but also another player to need Tommy John surgery. And it is very possible Harvey is simply untouchable, but the word is that the Mets have come calling about Xander Bogaerts, and there is no way Zach Wheeler, Jacob deGrom, or Noah Syndergaard is going to convince Cherington to give up his shortstop of the future. Harvey is the one player on this list that I would give up Xander Bogaerts for, and given the quality of the other names, that should say a lot about Harvey’s talent.

He sat out all of 2014 after his injury at the end of the 2013 season, but he was kicking in doors in his first full season in New York. In 26 starts, he posted an incredible 2.27 ERA and yet his FIP was an astonishing 2.01 (!) meaning he pitched even better than his stats show. If I were the Mets, Matt Harvey would be untouchable, but Sandy Alderson has a reputation for going against the grain (albeit with less success than Billy Beane…). I would give up Bogaerts for Matt Harvey, along with Owens and Double-A outfielder Manuel Margot, an astronomical prospect package for an astronomical talent.

Stephen Strasburg

Oct 3, 2014; Washington, DC, USA; Washington Nationals starting pitcher Stephen Strasburg (37) leaves the game in the sixth inning of game one of the 2014 NLDS playoff baseball game against the San Francisco Giants at Nationals Park. Mandatory Credit: Brad Mills-USA TODAY Sports

At 26 years old, Stephen Strasburg is the oldest name you will find in this slide show, which should say a lot about the type of players I am looking for. He is under control until 2017, which is just long enough to justify giving up Mookie Betts for. There is an odd man out in Washington’s rotation and with phenom Lucas Giolito waiting in the wings, the time to move a pitcher may be sooner rather than later for the Nationals. The speculation has been buzzing around long time rotation leader Jordan Zimmermann up to now, but Strasburg may be available.

There are very few pitchers with Strasburg’s potential, but Washington has to be thinking about extending another phenomenal talent in Bryce Harper. Both players will likely surpass $200+ million and it seems unlikely they could lock up that much money into two players. Harper has given them fits with his attitude and injuries but he is also the more talented of the two. Mookie Betts could solidify one of the weakest points of Washington’s lineup at 2B, and the Red Sox could also talk about a throw in player like Devin Marrero, who could potentially replace Ian Desmond in 2016.

Chris Sale

Aug 30, 2014; Chicago, IL, USA; Chicago White Sox starting pitcher Chris Sale (49) throws a pitch against the Detroit Tigers during the first inning at U.S Cellular Field. Mandatory Credit: Mike DiNovo-USA TODAY Sports

Chris Sale represents the most productive player on this list, and yet, unlike Harvey or Fernandez I would hesitate to give up Bogaerts for him. He is signed all the way through 2019 (his age 30 season) and yet something about his lanky frame makes me nervous. Not too nervous to give up Betts mind you, but given how hard he throws and the number of innings he accrues I do wonder if eventually the Tommy John bug will bite him in the next few seasons.

Now if Rick Hahn were only willing to deal Sale for Bogaerts, that wouldn’t necessarily end negotiations. Sale is arguably the most talented pitcher in the American League and he is only 25. He pitched to a 2.17 ERA, with a dazzling 10.8 K/9 that will play in any ballpark and because of this, if he were to be made available, the Red Sox would have to give strong consideration to giving up almost any player to bring him to Boston. But I don’t know if it is a decision I could make and it is the reason I write blogs rather than manage a baseball team.

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Think I’m way off? Not trading Mookie or Xander no matter the return? Leave comments, questions and your own trade ideas in the comments.