Investments with a Purpose: Engineering the 2018 Boston Red Sox
No team has won more World Series Championships than the Boston Red Sox, with four, in the
21st Century. With an immersive organizational philosophy of player development,
complemented with astute acquisitions via trade and free-agency, the Red Sox defied industry-
wide predictions and captured the Commissioner’s trophy for the second time in five years.
However, the road has not been without obstacles.
It is October 30th, 2013. The Boston Red Sox had won their third ring of the 21st century with
many veterans who have since faded into obscurity. With a now-vintage roster including Jarrod
Saltalamacchia, Ryan Dempster, and Mike Napoli, it had appeared at that their window of
contention had been quickly closing. With many of key player Jacoby Ellsbury set to hit free
agency and others bound for regression, the future was in doubt. However, there were bright
spots. On a team of aging veterans seemingly performing above their capabilities (including
Saltalamacchia’s career-high 2.7 WAR), a young star shined brighter than most. Xander
Bogaerts, the Red Sox top prospect, showed his immense promise by compiling a 0.3 WAR
during his 18-game regular season cameo and a solid 0.63 win-probability added in the
The first move to set up the Sox’s eventual 2018 title came on December 3rd, 2013, when
Ellsbury left the Boston for the rival Yankees. While it had been unpopular at the time, the
decision turned out to be a significant cost-saver as Ellsbury’s $153-million dollar contract has produced
a mere 95 OPS+ and a 9.8 WAR over his five years, missing the entire 2018 season. The Red
Sox goal for payroll flexibility certainly paid off, and while the 2014 season had been
underwhelming, finishing last in the AL East with 71 wins, it proved to be crucial in the team’s
Jacoby Ellsbury has been an expensive disappointment for the Yankees.
Key players in the 2013 run had regressed substantially in 2014, with players like Gomes and
Pedroia below-average offensive seasons. Bogaerts’ first full season proved to be a struggle, as
he posted a replacement-level 0.1 WAR and below-average 83 OPS+. However, the world was
introduced to the exciting Mookie Betts, a versatile player who could play both in the outfield
and second base, posting a 2.3 WAR and excellent 126 OPS+ while playing great defense. Betts
would develop to be one of the top players in baseball, winning AL MVP honors while leading
the Red Sox to the World Series in 2018 with one of the best overall seasons in recent memory.
The decision to trade staff ace Jon Lester to the Oakland A’s in his walk year netted them Yoenis
Cespdes, who they traded in offseason for eventual Cy Young winner Rick Porcello, one of the
key cogs in the 2018 machine. Young and flame-throwing reliever Joe Kelly who baffled the
Dodgers in the 2018 World Series also made his Boston debut in 2014, traded from the Cardinals
for John Lackey, the veteran with less than 2 years left. Eduardo Rodriguez, who the Sox
acquired from Baltimore for relief ace Andrew Miller, also turned out to be one of the more
reliable Boston arms in 2018, going 13-5 with an excellent 114 ERA+ and 10+ K/9. The most
significant move of the 2014 offseason, however, was the signing of Cuban mega-prospect Yoan
Yoan Moncada signing autographs for fans.
After failed signings of Pablo Sandoval and Hanley Ramirez, the 2015 season proved again to be
challenging, as the Red Sox finished dead last in the AL East. A bright spot came in the first-year
player draft as first-round pick Andrew Benintendi has been a great hitter (113 OPS+) and key
player since his debut. General Manager Ben Cherington, the man in charge of assembling the
2013 World-Series roster, was removed in favor of veteran and proven baseball executive Dave
Dombrowski, who fearlessly proceeded to invest and divest Boston’s organizational assets with a
purpose. Significant moves include acquiring David Price in the 2015 offseason, which has
proven to pay off in the long run, as he was on the mound in Boston’s Game 5 win against the
Dodgers in the 2018 World Series. Trading multiple high-potential, but raw prospects for all-
time great closer Craig Kimbrel appeared to have been a costly investment at the time, but
Kimbrel’s consistency has yielded him a 184 ERA+ in Boston, and made him a reliable stopper
in the playoffs.
The 2016 Season with Dombrowski at the helm proved successful, finishing 1st in the AL East in
David Ortiz’s last season. Rebounds by Dustin Pedroia and Hanley Ramirez coupled with a
stunning 9.7-WAR breakout by superstar Mookie Betts demonstrated excellent player
development infrastructure as the Red Sox surged back into relevance.
The 2016 offseason also proved consequential, as top-prospect Yoan Moncada was traded to the
White Sox for Chris Sale, arguably the best pitcher the Sox have had since Pedro Martinez.
Compared to Sale, who has posted a 175 ERA+ for Boston throughout his two years and 13.2
strikeouts per nine during his great tenure, Moncada has not lived up to the hype, leading the
MLB with 217 strikeouts. The 2017 offseason was highlighted by the value investments in J.D
Martinez, who anchored the 2018 lineup alongside Betts and had a 6.4-win career year, and
Mitch Moreland, who was an average hitter for the World Series team while playing solid
defense. Dombrowski pulled off two miraculous trades at the 2018 deadline as Steve Pearce and
Nate Eovaldi were acquired, both paying great dividends in the playoffs and fueling the eventual
The Red Sox model of player development, in the case of Mookie Betts and Xander Bogaerts,
smart trade market strategy, in the case of Chris Sale and Craig Kimbrel, and fearless free agent
acquisitions of J.D Martinez and David Price, helped maximize the combined portfolio value of
these players. The 118 games were won with long-term precision planning and appropriate
capital allocation, an approach that has served them well since the turn of the century.
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Written by Harrison Lee & Edited by Alexander Fleiss
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