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.