On October 28, 2007, the Boston Red Sox had just won their second World Series title in four years after an eighty-six year drought. In those eighty-six years, the New York Yankees won the Fall Classic a whopping twenty-six times. However, when Boston general manager Theo Epstein was asked about keeping pace with New York, he replied, “If someone wants to compare us to the Yankees based on winning and results, that’s an incredible standard. If they want to compare us to the Yankees in how we do things, that’s a little off-base.” It was a scathing shot at the rival Yankees and their method of building ballclubs since the turn of the new millennium – trading for the enigma Alex Rodriguez, signing the pricey Jason Giambi, and even “stealing” Red Sox outfielder Johnny Damon. Boston had just won two titles with a core of mostly homegrown players, led by Jon Lester, Jonathan Papelbon, Jacoby Ellsbury, and Rookie of the Year Dustin Pedroia. As the architect of the most successful team of the decade, Epstein had every right to be smug. However, looking at the results following his departure to the Windy City in 2011, it becomes clear that the Red Sox merely peaked on prom night and have failed to rebuild a consistent contender.

The 2012 Red Sox season was marred by injuries to key players, but twisted into a circus show led by the drama surrounding new manager Bobby Valentine. Valentine, hired to be fan favorite Terry Francona’s replacement, caused a stir in the clubhouse by speaking to the media on April 15th. Valentine complained about club hero Kevin Youkilis, “I don’t think he’s as physically or emotionally into the game as he has been for some reason.” Team leader Dustin Pedroia immediately came to his teammate’s defense, firing back, “That’s not the way we go about our stuff here. Maybe that works in Japan.” The rift between Bobby Valentine and his players was set in concrete, and Youkilis was traded on June 25th to the White Sox after 9 seasons in a Boston uniform. Despite reports that Valentine was demoralizing to young third baseman Will Middlebrooks, had ineffective communication with his own coaching staff, and created an overall toxic atmosphere in the clubhouse, upper management decided to stick with him in a season that saw Boston lose 93 games for the first time since 1966. Acquisitions Carl Crawford (7/142M), Andrew Bailey (signed to be the closer), and Marlon Byrd (suspended for PED use) were among the biggest disappointments in new GM Ben Cherington’s first year at the helm. The season came to a head on August 25th, when he pulled off one of the most unique blockbusters in baseball history; Boston dealt Josh Beckett, Carl Crawford, Nick Punto, and Adrian Gonzalez to the Los Angeles Dodgers (who inherited most of the money left on their contracts) in exchange for James Loney and four prospects. The intent of the move was to hit the reset button for 2013; shedding 250M worth of future salary while keeping most of the inner core. At the conclusion of the season, Bobby Valentine was fired after just one year in Beantown.

With the humiliation of 2012 behind them, the Red Sox made quick work to reload for 2013, signing free agents Shane Victorino, Mike Napoli, Stephen Drew, Jonny Gomes, and acquiring Jake Peavy at the trading deadline. With Dustin Pedroia, David Ortiz, Jacoby Ellsbury, and Jon Lester enjoying healthy and productive seasons, the imprint of Theo Epstein and his core led the team to a World Series championship that fall. The last go around for the group cemented Epstein’s legacy, but as the next two seasons unfolded, Ben Cherington and co. proved their inability to rebuild the team to continue contending.

After the successes of 2013, baseball pundits put the Red Sox back on the map as the team to beat in 2014. Few projected less than 90 wins and a postseason run. ESPN writer Gordon Edes made predictions that included an All Star berth for rookie Xander Bogaerts (who went on to hit .240) and a 5/125M extension for Jon Lester (who was traded mid season and signed with Epstein’s Cubs for 6/155M). Dustin Pedroia toiled through the worst season of his career with a meek .278 average and injuries to boot. Supposed Jacoby Ellsbury replacement Jackie Bradley Jr. hit .198 and was sent to the minors by seasons end. John Lackey was traded to St. Louis, where he experienced a renaissance 2015 while being paid the major league minimum salary (thanks to a unique clause in his contract that Boston declined to take advantage of). Jake Peavy was dealt to San Francisco, where he was a key contributor down the stretch for the Giant’s third World Series win in five years. The only key starter to remain was Clay Buchholz and his 5.34 ERA. Even 39 year old closer Koji Uehara was shut down by September due to fatigue. The sum of the 2014 season was a last place finish and 91 losses, the polar opposite what the “experts” projected.

It is important to note that criticizing baseball writers for their preseason predictions can be considered unfair; after all, the Red Sox were the defending World Champions. What is inexcusable however, is the fact that going into 2015, the Red Sox were once again declared favorites to win the AL East and beyond. Their acquisitions going into 2015 were of the staggeringly exorbitant variety. Outfielder Rusney Castillo was given a Cuban record 72M deal (and spent half the year in the minors, producing a paltry .253/.288/.359 slash line in the majors). Ben Cherington decided to sign the two most expensive third basemen on the market, Hanley Ramirez (4/88M) and Pablo Sandoval (5/95M). Sandoval was signed for his small sample size postseason statistics in San Francisco despite averaging 15 homers and a meager .279/.332/.416 line in the two years preceding the deal. In 2015, he battled conditioning issues, was suspended for using Instagram in the dugout, and produced an inept .245/.292/.366 line. Ramirez, a failed shortstop, was moved off of third base and into left field (a position he never played before) and provided consistent highlights for his bungling defense in front of the Green Monster. After April, he hit only 9 home runs with 31 RBI, and managed to hit even worse than Sandoval at a .238/.277/.367 clip. While making a combined 37M in 2015, Sandoval and Ramirez returned negative value on the investment with a collective -2.2 WAR. Ben Cherington’s other key acquisition was Rick Porcello (traded from Detroit for Yoenis Cespedes), who was due to become a free agent after 2015, was seen as a key trade chip given his success in 2014 with Detroit and his 2.2 HR% dating back to 2011. Instead, Ben Cherington decided to sign Porcello to a 4/82.5M deal before he had even thrown a pitch in a Red Sox uniform, to which Porcello responded with a 3.4 HR%, a 4.92 ERA, and an average of 10.3 H/9. Porcello’s trade value tanked and Boston is still on the hook for 82.5M, an amount he most certainly would not have received in the pitching rich free agent class of that offseason. Joe Kelly (acquired in the John Lackey deal) disappointed with a 4.82 ERA after predicting himself to win the AL Cy Young Award. Allen Craig (also of the John Lackey deal) proved that he is no longer a major league caliber player with a slash line of .152/.239/.203 after finishing 18th in the NL MVP vote as recently as 2013 (he is still on Boston’s payroll for 2/20M). Due to injury, Koji Uehara once again did not throw an inning in September. Overall, 2015 resulted in a last place finish for the second consecutive year. In August, longtime President and CEO Larry Lucchino stepped down from his positions and GM Ben Cherington resigned from his post. They were replaced by chief operating officer Sam Kennedy and well established new team president Dave Dombrowski.

Dave Dombrowski set to work quickly in his first offseason, making a splash by trading two of the top prospects in baseball (Manuel Margot and Javier Guerra among others) for closer Craig Kimbrel. The move brought in an All Star pitcher, but did require a hefty price considering the current going rate for elite relievers. Failed shortstop/third baseman/leftfielder Hanley Ramirez is being moved to another position he has never played before in first base while management crosses their fingers and hopes for the best. The big ticket free agent of the offseason, David Price, was lured to Boston by Dombrowski for a record 7/217M deal that ignored the modern conventional wisdom that players over 30 years old should be signed to lucrative long term deals. Naturally, baseball experts once again predict Boston to be one of the top teams in the league.

The lavish ways of the Red Sox in recent years echo those of the Yankees that Theo Epstein once conquered in October 2007. While most teams have taken on an economic approach to building a contender, the Red Sox have spent with reckless abandon and figure to continue that approach with their current management at the helm.  

When asked of his reasons for leaving Boston, Theo Epstein wrote in a column for the Boston Globe, “[C]oaches and executives should seek change after 10 years with the same team. The executive gets rebirth and the energy that comes with a new challenge; the organization gets a fresh perspective, and the chance for true change that comes with new leadership. This idea resonated with me. Although I tried my best to fight it, I couldn’t escape the conclusion that both the Red Sox and I would benefit from a change sometime soon.” In his tenure at the helm of Chicago, he has built a club that went to the 2015 NLCS and looks to be a top contender for years to come. His modus operandi remains the same, cultivating his core through shrewd trades, his farm system, and key free agents, such as NL Cy Young Jake Arrieta, two time All Star Anthony Rizzo, Rookie of the Year Kris Bryant, and top free agent Jason Heyward. Theo Epstein was the architect of the core of three Red Sox championship teams, including one that broke an eighty-six year curse. He has now built a core that gives Cubs the best shot they have had to break their own 107 year dry spell. While the Red Sox look to bounce back after three last place place finishes in four years, Theo Epstein and the Cubs have only one thing in mind – win the last ballgame to be played this fall.