9.27.15 – Ben Cherington Article

The following is an article written back at the end of August, 2015. It includes an evaluation of where Ben Cherington went right and wrong during his tenure as the Red Sox’s GM.

At the end of the 2012 season, with the Red Sox coming off of a September collapse that cost them a playoff berth, Theo Epstein chose to leave and become the Executive of Baseball Operations for the rebuilding Chicago Cubs, leaving the door open for Ben Cherington to make his mark on Red Sox Nation.

Something about Cherington that many baseball fans are unaware of, however, is that he had already made his mark in Boston almost 7 years earlier. Back in December of 2005 through January of 2006, during Theo Epstein’s absence from the team, Cherington had served as co-GM of the Boston Red Sox with current Chicago Cubs GM Jed Hoyer. It was during that time in which the Red Sox completed a trade with the Florida Marlins that would have a very significant impact on their future, shipping out a package of promising prospects (headlined by Hanley Ramirez and Anibal Sanchez) for a few MLB’ers, most notably SP Josh Beckett and 3B Mike Lowell. Cherington played a major role in the completion of this trade, a trade that would eventually lead to the Red Sox winning the 2007 World Series, with Josh Beckett in line as the team’s ace and Mike Lowell contributing 120 RBI’s in a stellar season. Because Epstein’s absence was only for a short while, Cherington and Hoyer never received the credit that they deserved for pulling off such a blockbuster.

Fast-forward to 2012, and Cherington was taking over a 90-win team loaded with talent. The pitching rotation was led by ace lefty Jon Lester, followed by Josh Beckett and promising youngster Clay Buchholz. The back of the rotation would be filled by the likes of Tim Wakefield, bullpen sensation Daniel Bard, and the once successful yet inconsistent Daisuke Matsuzaka. Andrew Bailey was also acquired to fill out the back of the rotation. Furthermore, with a line-up lead by Jacoby Ellsbury, Dustin Pedroia, Adrian Gonzalez, Kevin Youkilis, and Carl Crawford, the offense was once again expected to be a strength. Bobby Valentine was brought in to replace Terry Francona as Manager, and the Red Sox seemed poised to have a big season. Real life is different than a roster on paper, however, as Ellsbury and Bailey battled both injuries and inconsistency, the starting rotation underachieved, and Youkilis was traded mid-season to make room for a “rising star” in Will Middlebrooks. That same third baseman would be lost for the remainder of the season and would never reach his potential with the Red Sox. With the team struggling to compete in the AL East, Ben Cherington made his first, and potentially most significant, move as the Red Sox GM. Cherington shipped Adrian Gonzalez, Carl Crawford, Josh Beckett, and Nick Punto to the Dodgers, dumping their entire contracts, in exchange for a package of players and prospects, lead by James Loney, Allen Webster, and Rubby de la Rosa. While this clearly signified the Red Sox giving up on the season, and while none of the players received in the deal are still with the team, the trade can still be viewed as a major win for Cherington. The deal provided the payroll flexibility that would help to propel the Red Sox back into contention the following season.

Going into 2013, Cherington realized that some major retooling would be needed in order to bring the Red Sox back to the playoffs, even with SP John Lackey returning after a 2012 season lost to Tommy John Surgery. The first move was to replace Manager Bobby Valentine with former Red Sox pitching coach John Ferrell. Ferrell had worked under Terry Francona during the Red Sox’s World Series win in 2007, and seemed a much better fit for the job than Valentine had been. Following the organization’s policy of no contracts longer than 5 years, especially to pitchers, Cherington went about overpaying a handful of free agents on a bunch of short term deals. This list included 1B Mike Napoli, SS Stephen Drew, OF Shane Victorino, OF Johnny Gomes, SP Ryan Dempster, and RP Koji Uehara. Given the organization’s ability to work with one of the highest payrolls in the majors, this strategy proved to be an effective one; every single one of these signings would play a major role in what would become a championship season, the team’s third World Series win in a span of 10 years. Cherington would also trade away promising young SS Jose Iglesias at the trade deadline for veteran SP Jake Peavy, proving that he was willing to make tough deals in order to make a run at a championship. Peavy would prove to be important down the stretch as a replacement for the injured Clay Buchholz, who had been the team’s ace up to that point in the season. To this point, Cherington’s tenure with the Red Sox could only be described as a success.

Following their improbable 2013 World Series victory, Cherington seemed to have been too comfortable with the team’s roster going into the offseason. He would make few moves between November and the start of spring training in February. This also meant losing Jacoby Ellsbury and Stephen Drew to free agency, with the expectation that rookies, CF Jackie Bradley Jr. and SS Xander Bogaerts, could sufficiently replace them in 2014. He also chose to let 3B Will Middlebrooks retain his starting job at 3B, despite having been benched in the 2013 postseason for the previously mentioned Bogaerts. All of these moves, or lack thereof, proved to be the Red Sox’s downfall, as they would finish the season in last place for the second time in just three years. The only potential positive form the lost season was that Cherington seemed to utilize the trade deadline as an opportunity to retool for the following season, giving fans hope for another quick turnaround. As result, however, staff ace and fan favorite Jon Lester was traded for power-hitting outfielder Yoenis Cespedes, SP John Lackey was moved for struggling first baseman Allen Craig and young fireballer Joe Kelly, and perhaps most significantly, RP Andrew Miller was traded for pitching prospect Eduardo Rodriguez.

The quick rebuild has proven to be another black hole on Cherington’s resume thus far, as he has failed to fill in the holes that were left from moving such a large part of the team’s core from 2014. The 2014 offseason seemed to have the Red Sox in a perfect position to bounce back, as they boasted one of the top 5 farm system’s in baseball. Futhermore, Xander Bogaerts was set to take a step forward in his sophomore season, and the outfield was filled with talent, ranging from Cespedes, to the athletic Mookie Betts in center, to Cuban Rusney Castillo in right. Interesting to note, Castillo represents the only player in Cherington’s tenure as GM who received a contract longer than 5 years, signing for 7 years at over 70 million dollars. The biggest areas of need for the team were clearly at SP and 3B. Reverting back to their heavy spending ways, the Cherington went ahead and signed Pablo Sandoval to a 5 year, 95 million dollar contract, and also brought in Hanley Ramirez to play left field, signing him for 4 years at 88 million dollars. He then traded Yoenis Cespedes for SP Rick Porcello, also extending his contract for another 82.5 million dollars over 4 years. Looking to further bolster the rotation, Cherington traded for SP Wade Miley from Arizona, shipping off Allen Webster and Rubby de la Rosa (acquired in the 2012 Dodgers trade), and also signed SP Justin Masterson to a 1 year contract. With all these additions, however, Cherington failed to acquire an ace to front the rotation, instead choosing to hold on to the team’s prospects and assets, rolling out a rotation of all number 3 and 4 type pitchers. He also failed to build a competitive bullpen, with the only significant moves being the resigning of closer Koji Uehara and the signing of RP Alexi Ogando. Always sticking in Red Sox fans’ minds as a result of this entire ordeal is the failure of Cherington and company to resign SP Jon Lester, who opted to join the Cubs on a massive 6 year, 155 million dollar contract. This was more than double Red Sox’s initial offer of 4 years and 70 million that they offered him during spring training in 2014. It will never be clear if it was Cherington or the front office who suggested handling the negotiations the way they did, but it would prove to be the beginning of the end for Cherington in Boston. Almost 5 months through the 2015 season, the Red Sox are still without an ace, ranking as one of the league’s worst teams in almost every significant pitching category. They have seen underachievement from the likes of Pablo Sandoval, Justin Masterson and Rick Porcello. They have dealt with injuries to core pieces such as Clay Buchholz and superb catching prospect Christian Vazquez. They have failed the Hanley Ramirez experiment in left field, and they have been forced to trade away spare parts in Mike Napoli and Shane Victorino during the deadline for next to nothing in return. Allen Craig, acquired over a year ago from the Cardinals, has struggled so mightily in the Majors that he has become a nobody in Boston’s minor league system. Yet, even with all of these issues, Cherington has left new Executive Dave Dombrowski with a very promising future in Boston, primarily due to success in building the strongest farm system in all of baseball.

While the Red Sox will go into the 2015 offseason with some expensive contracts on the books (see Ramirez, Sandoval, and Porcello), the size of the market in Boston makes them capable of building a team around players with such deals. The key in doing this will be to build from within, something that Cherington clearly emphasized during his four years with the organization. Cherington seemed to utilize all of his resources to the fullest extent when it came to acquiring young talent, whether that be internationally, through the amateur draft, or in trade. Boston currently has 7 players on its 40-man roster who have appeared on a Top 100 prospects list between 2014 and 2015: Xander Bogaerts, Mookie Betts, Blake Swihart, Henry Owens, Brian Johnson, Matt Barnes, and Eduardo Rodriguez. Rodriguez was acquired in the 2013 trade deadline deal with Baltimore, and If he can find more consistency, then he possesses top of the rotation potential. In regards to amateur scouting, Cherington drafted Brian Johnson in the 2012 draft, along with slick-fielding SS Deven Marrero. In 2013, Cherington chose tall lefty Trey Ball, who is still working to find consistency in his delivery because of his size, but has plenty of time to develop. In 2014, the Red Sox used their top three picks on Michael Chavis, Michael Kopech, and Sam Travis. Travis and Kopech seem to be finding their strides in the minors (though Kopech is currently suspended for using a banned substance), while it is still a bit too early to judge Chavis. 2015 first round pick out of college, Andrew Benintendi, has had a great introduction to professional ball, demonstrating both power and speed while playing solid CF defense at A ball. Internationally, Cherington has also been very active, signing 2B Yoan Moncada to a record 31.5 million signing bonus that comes with a 100% penalty for exceeding the spending limit. Young pitchers Anderson Espinoza and Christopher Acosta represent other important signings, with Espinoza’s tools reminiscent of a young Pedro Martinez. And no one can forget two of Boston’s other top international prospects, speedy CF Manuel Margot and power-hitting 3B Rafael Devers.

Thus, given all of the pieces that Cherington has provided to Dombrowski, the Red Sox have a strong chance of returning to contention in 2016. While most Red Sox fans will be quick to criticize Cherington’s downfalls (which does admittedly include 3 losing seasons), they should not be too quick to push aside his successes (shedding salary in 2012, retooling and winning a world championship in 2013, and building one of the best farm systems in baseball). Only time will tell just how effective Cherington’s tenure in Boston turned out, but I am willing to bet that there will be far more positives in the long run then their appear to be as of now.


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