Red Sox struggles after winning World Series are nothing new

The Red Sox have a history of struggling after winning the World Series. What does this mean heading into the 2020 season?

We all know repeating as champions, in any sport, is difficult despite certain teams that make it look easy. While we’ve seen recent dynasties in the NFL (the Patriots) and NBA (the Warriors), we haven’t seen one in MLB since the Yankees’ run from 1996-2003 where they won six pennants and four World Series. The Red Sox have been the most successful MLB franchise of the last twenty years, winning four pennants and four World Series, but no one would consider them a dynasty. Beyond the sustained excellence year after year, dynasties win multiple championships with many of them clustered together and that’s something the Red Sox haven’t done.

As we slog through this tumultuous Red Sox offseason, it got me thinking about how the Red Sox have always seemed to struggle to follow up a World Series-winning season. Four times in the 21st century the Red Sox have hoisted the Commissioner’s Trophy and four times, they’ve failed to repeat. That in and of itself is certainly not something to criticize them for, but only once did they mount a credible follow-up postseason run and twice, they failed to even qualify for the postseason the year after winning it all.

Let’s take a look at each World Series follow-up campaign and try to see if there are any lessons learned when looking toward the upcoming 2020 season.

After winning the World Series for the first time in eighty-six years and (if you buy into this stuff) breaking the Curse of the Bambino, expectations were high that the Red Sox could repeat as champions. There was a fair amount of turnover from 2004 to 2005 as the team lost Pedro Martinez, Derek Lowe, and Orlando Cabrera to free agency while they signed Edgar Renteria, David Wells, and Matt Clement to replace them. With the majority of the championship-winning squad coming back, it seemed as though the team was set to make another deep run in October.

While the 2005 Red Sox went an excellent 95-67 and finished second in the AL East while earning the American League Wild Card, their luck ran out in the ALDS where they were swept by the eventual World Series champion Chicago White Sox. While the Red Sox had a very good season, it never felt like they quite gelled as a team.

Wells was their best pitcher in 2005 and went 15-7, but he was forty-two years old and ran out of gas by the end of the season. Matt Clement was hit in the head by a comeback line drive during a July game and was never the same and Boston never really had a chance in that series.

At the time, no team had repeated as champions since the 1998-2000 Yankees and the Red Sox certainly put up a good fight, but things changed in 2006 when they slipped to 86-76 and finished third in the division and out of the postseason. With Johnny Damon leaving in free agency after 2005, then-GM Theo Epstein overhauled the team heading into 2007 for the next phase of the Red Sox championship decade.

The Red Sox came back strong in 2007 by going 96-66 and winning the AL East for the first time since 1995. After surviving a rugged ALCS against the Cleveland Indians by coming back from a 3-1 deficit, the Sox swept the Colorado Rockies in the World Series for their second title in three years. With young new players like Dustin Pedroia, Kevin Youkilis, Jon Lester, and Jacoby Ellsbury joining up with veterans Curt Schilling, David Ortiz, and Jason Varitek and new additions (via trade) Josh Beckett and Mike Lowell, the Red Sox looked poised to mount a strong season in 2008.

For the only time this century, the 2008 Red Sox had a strong follow-up to a championship season and came very close to repeating. The 2008 team went 95-67 but finished second in the division to the Tampa Bay Rays, settling for the Wild Card instead.

Led by Pedroia’s MVP season and basically the same players as the year before, Boston took Tampa to Game Seven of the ALCS and was a hair’s breadth from winning the game. I still remember the agony when JD Drew was called out on a check swing with the bases loaded late in the game which ended in a 3-1 Tampa victory. In his book, Terry Francona said that to this day he considers the 2008 team to have been better than the 2007 squad.

The 2009 Red Sox again went 95-67 and finished second in the division, but bowed out in the ALDS by getting swept. Things got worse in 2010 with an 89-73 finish but 2011 looked like it would be the year they’d get back to the Series. Theo Epstein traded for slugger Adrian Gonzalez and signed free agent Carl Crawford. On paper the team looked stacked and like they’d run roughshod over the entire league.

They were cruising heading into September, behind the Yankees for the division lead but nine games ahead of the Rays for the Wild Card. Incredibly, the team went 7-20 in September and lost on a blown save in the ninth inning against the Orioles to finish in third place and out of the postseason.

It turned out there were problems in the clubhouse all that season which were personified in the “fried chicken and beer” scandal involving Lester, Beckett, and John Lackey. Theo Epstein left to be the GM of the Chicago Cubs, manager Terry Francona was fired after the season, and Bobby Valentine was hired as his replacement.

The 2012 season was the nadir of this ownership group’s tenure, with the Red Sox going 69-93 and finishing in last place. Valentine was fired, former pitching coach John Farrell was hired away from Toronto to manage the team and GM Ben Cherington cleaned house and signed a bunch of low risk/high-reward players heading into the 2013 season.

Nobody was expecting much from the 2013 Red Sox, but they used the horrific Boston Marathon bombing as a rallying cry to unite the team and city and, combined with career years from pretty much all of the new guys they signed, rode that wave all the way to a World Series victory. Rookie manager John Farrell turned the same trick Terry Francona had done nine years prior and won a title in his first year. However, his follow-up season would be far worse than his predecessor’s.

Farrell and the 2014 Red Sox followed up the worst-to-first seasons of 2012 and 2013 with two last place finishes in 2014 (71-91) and 2015 (78-84). A huge part of it was roster turnover and players who caught lightning in a bottle in 2013 crashing back down to earth. The rosters were steadily less talented, injuries hampered them, certain players reached the end of their useful shelf life with Boston, and the ill-advised Pablo Sandoval blunder put the final nail in the coffin.

However, these years weren’t all bad as they allowed young homegrown stars like Xander Bogaerts, Mookie Betts, and Jackie Bradley time to grow and develop. Things finally got better in 2016 when the team reeled off the first of three consecutive seasons winning the AL East. After replacing Farrell with Alex Cora for the 2018 season, they got back to their championship ways by having the greatest season in franchise history and winning their fourth World Series since 2004.

It seemed as though this juggernaut of a team would finally be the one that would mount a real title defense the next season, especially since almost the entire team was left intact for 2019. Of course, we all know how that turned out…

If history is anything to go by (and it usually is), the Red Sox are probably in for another rough season in 2020. As we all know, there’s been a lot of turmoil with a new President of Baseball Operations in Chaim Bloom, mixed messages coming from ownership, uncertainty surrounding the long-term status of Mookie Betts, and a now-vacant managerial seat with the firing of Alex Cora. With little having been done to improve the talent on the roster this offseason, it looks like the Red Sox will have a hard time contending for the Wild Card.

John Henry himself recently lamented that he doesn’t understand why the Red Sox always struggle after winning a World Series. I’ve wondered this myself over the last two decades. While other teams that win it all like the Astros, Giants, and Cardinals are able to remain competitive for a few years afterward and even teams who come up short like the Yankees and Dodgers are able to do so, for whatever reason the Red Sox have not been able to do that apart from 2008.

Why is this? Part of it is the so-called “World Series hangover” which, as we saw in 2019 especially, is very real. After playing longer than every other team and in more pressure-packed games, the mental and physical toll carries over into the next season. This can manifest itself in injuries, fatigue (physical, mental, or both), and complacency. The Red Sox have seemed to suffer from all of these in their follow-up seasons (and especially in 2019).

There is also the matter that it is exceedingly and increasingly difficult to keep championship teams together long-term in any sport, including MLB. Everyone wants a piece of that winning formula after a team wins and free agents are ripe for the picking. Oftentimes players want more money after they win, especially if they had a significant role in getting there. Egos grow and clash, demands for playing time escalate, and the spoils of victory exacerbate issues that had been precariously kept in check before the team won.

None of this, however, is unique to the Red Sox, so why do they always seem to fall into this trap? I think it’s a combination of the expectations and pressures of playing in the Boston market and an ownership group that’s willing to spend, but not always wisely. The team’s player development system also leaves something to be desired as while they’ve developed a lot of quality homegrown position players over the last twenty years, their track record developing pitchers in that time space has been dismal. As we all know, the key to sustained success usually begins quality pitching.

Heading into 2020, the Red Sox seem to be pinching pennies when it comes to improving the team before making a run at Mookie after the season to sign him long-term. There’s a leadership vacuum at manager with less than a month until spring training and the cloud of MLB’s potential punishment for Alex Cora’s involvement with sign stealing during the 2018 season hanging over the team. With several holes still left to fill on the roster (second base, first base, a closer, a fifth starter), it looks as though the Red Sox post-championship woes are set to continue for at least another year.