Boston sports fans have had it good for 20 years, but what was the best?

Barry Chin
The Patriots have treated their fans to six championship parades in the last 20 years.

For better or worse, your loyal scrivener isn’t exactly one to resist viewing Boston sports through a prism of nostalgia even on typical days.

Perhaps you’ve noticed. I’d blabber in this space about the heydays of, oh, Fred Lynn and Stanley Morgan weekly if I could get clearance. Terry O’Reilly and Dennis Johnson, too. At least biweekly, anyway.

Most of the time, unabashed sentimentality must yield, understandably, to the noteworthy sports news of the day, hour, and moment. But this past week brought not one, but two, rare situations where the past and present collide, and the reminder comes of just how good we had it around here for so long.


A week ago Tuesday, David Ortiz, the slugger who delivered countless clutch hits while delivering the Red Sox from generations of disappointment, was elected to the Baseball Hall of Fame on the first ballot.

Four days later, ESPN reported that Tom Brady, fresh off a season of shredding defenses at 44 years old, would retire after 22 NFL seasons, news that he made official on Tuesday.

Brady and Ortiz, in that order, were the main athlete avatars of a nearly two-decade run of Boston sports dominance. From Feb. 3, 2002 (when Brady led the Patriots past the St. Louis Rams for their first Super Bowl victory) to Feb. 3, 2019 (when Brady led the Patriots past the Los Angeles Rams for their sixth Super Bowl victory), Boston’s four most-established professional sports teams won 12 championships — four by the Red Sox, and one each by the Bruins and Celtics, along with the Patriots’ hoard of a half-dozen Lombardi Trophies.

Thinking about the storybook achievements of Brady and Ortiz and that golden age of Boston sports as a whole over the past few days made me wonder something: When was the very best time among those best of times?

I don’t mean a specific moment (I’m not sure we could narrow it down to just one) or day (though I’ll argue that the Bruins’ championship parade on June 18, 2011, might have been the sunniest day in terms of weather and mood in the city’s lore).


What I do mean: When did Boston’s teams have the most going right at once? When were mutual championship aspirations at the pinnacle? When was the highest concentration of good times, if you will?

There are some seasons and candidates that come immediately to mind.

The Red Sox exorcised all ghosts in October 2004, and four months later the Patriots won their third Super Bowl in four seasons. But the Bruins, after finishing tied for third in the NHL with 104 points in the regular season, were bounced by old nemesis Montreal in a seven-game conference quarterfinal series. And all you need to know about the 36-win Celtics is that Ricky Davis was their second-leading scorer.

The Red Sox and Patriots collected matching championships again in 2018. The Sox won a franchise-record 108 games and rolled through the Yankees, Astros, and Dodgers in the postseason, while the Patriots beat the Chiefs in Kansas City in an epic AFC title game before thwarting the Rams in the Super Bowl. The Celtics and Bruins were pretty darn good in ‘18, too. The Celtics took LeBron James and the Cavaliers to seven games in the Eastern Conference finals, while the Bruins racked up 112 points in the regular season before bowing to the Tampa Bay Lightning in five games in the second round of the playoffs.


I’ll hear you if you want to say ‘04 or ‘18 are the years that should be most savored. But I think I can narrow this whole thing down to a month: October 2007. The Red Sox, featuring what might have been the most complete team they’ve ever had, were overwhelming the Colorado Rockies for their second World Series title in four years.

The Patriots, in a Spygate-induced fury, were rampaging through the NFL. On Oct. 28, the day the Red Sox completed their World Series sweep, the Patriots improved to 8-0 (on their way to 16-0) with a 52-7 throttling of Washington. Through those first eight games, the Patriots averaged 41.4 points. Yes, the Giants left them with a devastating blemish in the loss column in Super Bowl XLII, but they still deserve a spot in the conversation about the best teams in NFL history. They dominated.

Also that October, the Bruins … well, they jumped to a 6-3 start in a season that would end — stop me if you’ve heard this before — in a conference quarterfinals loss to the Canadiens. But the Celtics, now they were on the verge of something special, having acquired Kevin Garnett and Ray Allen in the offseason to join Paul Pierce in a new Big Three.

The Celtics opened their new era with a 20-point win over the Wizards on Nov. 2, then proceeded to win 29 of their first 32 games en route to capturing their first NBA championship since 1985-86. Garnett was the fulcrum of that team, but this seems a fitting place to point out that Pierce never believed LeBron or Kobe were better than him, and on many nights that season, he was right.


In 2007, the Boston sports scene included Brady, Ortiz, Pierce, Garnett, Allen, Randy Moss, Bill Belichick, Manny Ramirez, Dustin Pedroia, Jon Lester, Tedy Bruschi, Zdeno Chara, Rajon Rondo, Terry Francona, Doc Rivers, Mike Lowell, Wes Welker, Junior Seau, Rodney Harrison, Tim Thomas, and Patrice Bergeron (for just 10 games), among many, many others.

We’ve been so fortunate to have so many good times and watch so many stellar teams these last 20 or so years. But October 2007 may have been the height of all heights. That there’s even a debate about that is further confirmation of just how good Boston fans have had it.


This discussion has ended. Please join elsewhere on