Eight years ago, the greatest team in Boston Red Sox history capped off a remarkable season by winning their fourth World Series title in 14 years, the most of any team in baseball since 2000. Now, only eight seasons removed from that historic 2018 season, the Red Sox operate as a mere shell of themselves. 

The 2018 roster was a masterclass in roster building by former GM Ben Cherington and President of Baseball Operations Dave Dombrowski. 

Cherington, who served as general manager from 2011-2015, had the most thankless job of the two, serving as the guy before THE GUY. However, the greatest team in Red Sox history would never have taken shape without his work as both GM and vice president of player personnel under Theo Epstein. Cherington helped build much of the young core, including selecting Jackie Bradley Jr. in the first round and Mookie Betts in the fifth round of the 2011 MLB Draft. Cherington added to that core by trading reliever Andrew Miller to the Baltimore Orioles for pitching prospect Eduardo Rodriguez ahead of the 2014 trade deadline, drafting 2015 Golden Spikes Award winner Andrew Benintendi with the seventh overall pick in the 2015 MLB Draft, and signing top international free agent Yoan Moncada. 

By the time Cherington gave way to Dombrowski, both Betts and Bradley were emerging as core pieces, with Betts establishing himself as one of the best players in baseball, joining shortstop Xander Bogaerts who was establishing himself as the next great leader of the team as David Ortiz’s Hall of Fame career drew to a close. Benintendi and Moncada inched closer to being big-league contributors. 

Dombrowski, doing what he does best, took a team ready to open its contention window and swung that door wide open. With Benintendi, Bradley, and Betts as the future outfield group, Dombrowski built a package around top prospect Manuel Margot to land San Diego Padres All-Star closer Craig Kimbrel ahead of the 2016 season. After the Boston rotation finished the 2015 season with a 4.39 ERA, the seventh-worst in baseball, Dombrowski opened the checkbook, signing left-hander David Price to a seven-year, $217-million contract, the largest contract ever for a pitcher at the time. 

After winning the American League East in 2016, Ortiz’s Hall of Fame career came to an end in the ALDS, when the Red Sox were swept by Cleveland. With a pitching staff that still didn’t have quite enough, Dombrowski used his remaining prospect capital, Moncada, pitcher Michael Kopech and infielder Luis Alexander Basabe to land five-time All-Star and perennial Cy Young Award candidate Chris Sale from the Chicago White Sox. Perhaps most impressive about Dombrowski’s shrewd trades was that he identified pieces worth keeping, like Benintendi and Rafael Devers, both of whom were initially asked for in exchange for Sale, instead of dealing from a group of prospects that amounted to little in the big leagues. 

After a second straight AL East-winning season ended in the division series, this time against the eventual World Series champion Houston Astros in 2017, Dombrowski made the final moves to build the greatest team in franchise history. Shortly after the season ended, the team fired manager John Farrell and replaced him with Astros bench coach Alex Cora. After Hanley Ramirez struggled to replace Ortiz’s production at DH, Dombrowski opened the wallet again, shelling out $110 million over five years for J.D. Martinez to provide both a major spark and veteran leadership to a relatively young lineup. As the 2018 season progressed, minor needs arose and were filled with minor but impactful trades, landing first baseman Steve Pearce and starter Nathan Eovaldi. 

Those moves culminated in a franchise-record 108-win regular season that steamrolled its way to a World Series, losing only three playoff games. The formula was simple: identify your core building blocks, then use your remaining prospect capital and free agency to supplement them with veteran leaders and contributors. 

With Sale at the height of his powers and the core of Benintendi, Betts, and Bogaerts under contract for several more seasons, the Red Sox seemed ready to become baseball’s next dynasty. 

Instead, the Red Sox have slowly become a shell of that organization that was willing to do whatever it takes to win. After a disappointing 2019 season, Dombrowski was fired and replaced by Rays executive Chaim Bloom as ownership sought a more sustainable model built on homegrown talent. The team decided not to extend Betts, and he was traded alongside Price to the Los Angeles Dodgers before the 2020 season. From that point on, the 2018 World Series team was slowly disassembled until June 2025, when Devers, the last remaining piece of that roster, was traded to the San Francisco Giants. 

Bloom did well in what ownership asked of him; he found a trade partner for Betts and a taker of Price’s contract and rebuilt the depleted farm system into one of the best in baseball, thanks in part to drafting outfielder Roman Anthony. However, after serving his purpose, Bloom was quickly dismissed after three seasons, and the team replaced him with current Chief Baseball Officer Craig Breslow just as the team’s contention window began to open.  

While it’s not a one-for-one comparison, Breslow effectively took over for Bloom around the same time Dombrowski replaced Cherington. Young players like Wilyer Abreu and Ceddanne Rafaela were establishing themselves at the big-league level, while top prospects Anthony, Mayer, and Kyle Teel were nearing their big-league debuts. In some ways, history did repeat itself. Breslow swung a trade for White Sox ace Garrett Crochet, sending Teel, Braden Montgomery and Chase Meidroth to Chicago. The team also splurged in free agency to land All-Star starter Ranger Suarez. 

Like Dombrowski with Pablo Sandoval and Hanley Ramirez, Breslow took on a team with bloated contracts for underperforming players, Trevor Story and Masataka Yoshida, in the same vein. 

However, in other ways, things could not be more different. While Dombrowski traded away pieces that were relative busts compared to their prospect value, Meidroth, Teel, and Montgomery have become valuable pieces for Chicago, while the Red Sox struggled to get production from their catchers and second basemen. Meanwhile, Mayer, once considered untouchable in trade talks for Crochet, fizzled out in Boston and was traded to San Francisco for reliever Erik Miller. Dombrowski was given the liberty to simply designate both Sandoval and Ramirez for assignment, eating their contracts. Breslow hasn’t had that same flexibility with Yoshida and Story, who continue to create roster-construction issues. 

After signing third baseman Alex Bregman ahead of the 2025 season, it looked like the team was using at least some of the model that built the 2018 team. Bregman immediately ingratiated himself with Mayer, Kristian Campbell, and Anthony, so much so that Anthony said nobody has helped him at the big league level as much as Bregman.

However, Bregman’s tenure in Boston lasted only one season, as he opted out of his deal and signed with the Chicago Cubs. The reported reason for his departure was a supposed organizational policy against no-trade clauses. To make matters worse, Bregman’s original signing led to organizational dysfunction that strained the relationship between the team and Devers, and ultimately led to the trade that sent him to the Giants. 

Unlike Betts, Benintendi, or anyone else on that young core in the mid-2010s, Anthony entered 2026 without Devers's power or Bregman’s leadership and with the pressure on him to be THE GUY on offense. Through injuries and underperformance, the 22-year-old fell well short of those expectations while still posting respectable numbers. Ultimately, the Red Sox are not THAT far away from competing with the pennant-winning Tampa Bay Rays and Milwaukee Brewers. However, the way the roster is constructed, they needed everything to break their way: Anthony needed to immediately become an MVP candidate, Story needed to stay healthy and perform up to his 2024 numbers, Mayer needed to both stay healthy and take a step forward at the plate, and the pitching staff had to live up to its billing. Ultimately, only the latter happened, and for the second season in a row, the Red Sox season ended on the field at Yankee Stadium in the wild card round.

As the offseason approaches, the team has the same offensive needs it did last year: it lacks the true alpha in the heart of the lineup that opposing pitching staffs circled in pregame meetings and said, "This guy cannot beat us." However, since Dombrowski's dismissal, the organization has done little to show they still have the 'win at all costs ' mentality that both Dombrowski and late team president Larry Lucchino possessed. Instead, the team seems more than happy to build a team good enough to draw fans to Fenway Park throughout the summer months and make the playoffs, with anything beyond a simple playoff appearance seen as an added bonus. 

Team president Sam Kennedy can sit at the end-of-season press conference and reaffirm that the ownership group is still as committed to the Red Sox as they ever have been, but actions speak louder than words, and it's time for the Red Sox to get back to being serious about building a true World Series contender, not one that COULD win if everything breaks their way.