The most crushing losses in Boston sports history

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By Sean Sylver, 98.5 The Sports Hub

It’s false bravado, this “city of champions” stuff. 

Boston sports fans are masochists at heart.

Why else would we live here as opposed to, say, anywhere that doesn’t combine miserable weather, astronomical housing prices and substandard public transportation?

There are plenty of reasons why it’s a wonderful place to live. But we just love to talk about how miserable we are. See? I just did it.

It’s a part of our sports DNA. We wear the “B” through thick and thin (well, the Patriots have a flying Elvis and the Celtics a leprechaun spinning a basketball on one finger, but you get the picture), and our birthright has served us incredibly well the past two decades. Sporting dominance has become such a part of the fabric of the region that we’ve reached a point where literally the only celebrities from here are athletes or people who have been dead for 200 years.

We’ve gotten a ton of parades. We were brazen enough to suggest a “Boston sports grand slam” earlier this spring, when the Celtics still had a pulse and the Bruins hadn’t yet thawed from the combined heat of thousands of phones playing Pam Beesly and Jim Halpert social media videos on loop.

The Bruins hoisted the Cup just eight years ago. Blues fans had never seen their team win and they’ve been around since the NHL expanded from six to 12 teams and Bobby Orr still sported a wiffle.

But for dyed-in-the-wool Bruins fans, the 2019 Stanley Cup Final was a matter of extreme importance. Baseball is boring, anyways, the NBA is rigged, and you weren’t even much of a Patriots fan before 2001. OK, maybe we’ll count the Bledsoe years. But the Cup was the white whale.

Ryan O'Reilly of the St. Louis Blues hoists the cup after defeating the Boston Bruins 4-1 to win Game Seven of the 2019 NHL Stanley Cup Final at TD Garden on June 12, 2019 in Boston, Massachusetts. (Photo by Patrick Smith/Getty Images)
Ryan O'Reilly of the St. Louis Blues hoists the cup after defeating the Boston Bruins 4-1 to win Game Seven of the 2019 NHL Stanley Cup Final at TD Garden on June 12, 2019 in Boston, Massachusetts. (Photo by Patrick Smith/Getty Images)

It stinks. It hurts. It’s been a few days and we’ve gained some perspective on the matter; enough time to realize that we need to be even more miserable. Behind the puffed-out chests of fans who’ve observed 18 appearances in a championship final by the Big Four Boston sports teams since the turn of the century (with a 66 percent success rate) are hearts that depend on the pain and suffering of sports to keep them beating.

So it’s time to let it all out. With a fresh entry to the debate, let’s bring out the most painful losses in Boston sports history…

Celtics division

The C’s rolled up so many titles during their first four decades of existence that it’s hard to identify examples of torment that persisted for more than a single offseason. You can lament Boston’s two NBA Finals losses to the Lakers in the 1980’s, particularly the 1987 series that featured Kevin McHale playing on a broken foot and Magic Johnson’s “Junior, Junior” skyhook that cemented LA as the team of the decade, but it was still pretty good era for fans of basketball in Boston. 

The 1982 Conference Finals, a 4-3 loss to the Sixers and the genesis of the “Beat LA” chant: Just another casualty of a hyper-competitive run for the Green. 

Way back in 1973, when the Knicks were actually good, they beat Boston in seven on the way to their second title in four years. And the Celtics won it all the following season.

The 22-year drought following the 1986 championship win over the Rockets was largely devoid of meaning – plenty of bad seasons, some decent ones, too, but nothing resembling a Finals run. Then Danny Ainge’s new Big Three came to town: A veteran unit with a distinct three-year window, and Boston responded with another championship.

BOSTON - JUNE 17: Paul Pierce of the Boston Celtics celebrates with the NBA Finals MVP trophy after defeating the Los Angeles Lakers in Game Five of the 2008 NBA Finals on June 17, 2008 at TD Garden. (Photo by Elsa/Getty Images)
BOSTON - JUNE 17: Paul Pierce of the Boston Celtics celebrates with the NBA Finals MVP trophy after defeating the Los Angeles Lakers in Game Five of the 2008 NBA Finals on June 17, 2008 at TD Garden. (Photo by Elsa/Getty Images)

The C’s found themselves back in the Finals two years later, following a Kevin Garnett knee injury, this time trying to prevent a Lakers repeat and snare another trophy before their window closed. But they relinquished a 3-2 series lead headed back to Los Angeles and gifted Kobe Bryant his fifth ring during an abysmal fourth quarter of Game 7.

For some reason, their fingers remained in the window even after it slammed shut, and they stuck around to repeat history in the Conference Finals against the Heat in 2012 - LeBron dismantling them at the Garden in Game 6 before they wilted in the Miami sun.

Bruins division

Even greater than the Celtics’ 22-year title layoff was the Bruins’ 39 years of wandering in the hockey desert. That doesn’t mean they didn’t get to the doorstep plenty of times. 

They were cannon fodder for Stanley Cup champs in Edmonton in 1988 and 1990, as well as Pittsburgh in the Conference Finals of 1991 and 1992 (with Ulf Samuelsson derailing Cam Neely’s career along the way). But the B’s were competitive for most of that span, at one point making 29 consecutive postseason appearances.

The 1970’s Bruins just so happened to run into the Broad Street Bullies of Philadelphia, and following the departure of Bobby Orr, faced Guy Lafleur and Co. three straight times to close out the decade. All losses. Say “too many men on the ice,” to a B’s fan of a certain vintage and get ready to hear about it.

This recent run, with three Finals appearances in nine seasons, has provided its share of missed opportunities. Hockey has the reputation of the best postseason out of the four major sports, and the Bruins have milked every bit of drama out of the experience, pushing an exhausting 11 series to the seven game limit over the past dozen seasons. 

The Eastern Conference semifinals loss to the Flyers in 2010 ranks among the most epic postseason collapses in history. They were minutes away from forcing a Game 7 of the Stanley Cup Final in 2013, only to succumb to a late Blackhawks surge. The 117 point, Presidents’ Trophy winners of 2014 were washed away by the Habs in seven games.

This time around, a veritable Red Sea of contenders parted for the Bruins early, putting the Cup in Boston’s field of vision the minute the Maple Leafs were out of the picture. Even in the midst of a bruising series with St. Louis, during which the B’s dropped two of the first three in their own building, and with the top two lines failing to make much of an impact in the box score, the outcome for Game 7 seemed preordained. 

Then, Wednesday night happened. 

Like the Celtics’ window a decade ago, the Bruins woke up Thursday with pinched fingers (plus a cracked jaw and maybe a punctured lung or two, because hockey).

BOSTON, MASSACHUSETTS - JUNE 12: Tuukka Rask #40 of the Boston Bruins reacts after his teams 4-1 loss to the St. Louis Blues in Game Seven of the 2019 NHL Stanley Cup Final at TD Garden on June 12, 2019 in Boston, Massachusetts. (Photo by Bruce Bennett/Getty Images)

Patriots division

Born in 1960, the Patriots are the freshest face among Boston’s Big Four. We mentioned the Celtics’ decades of success, occasionally marred by missteps in big games. The old Patriots barely ever played in the big games. And when they did, they lost big. 

Take the Super Bowl blowout at the hands of the 1985 Bears. Or Desmond Howard making like Billy in a Family Circus cartoon, leaving cleat tracks all over the New Orleans turf in 1997. 

One exception was the 1976 AFC playoffs, the franchise’s first taste of the postseason since the 1963 AFL title game (where they were thumped by the Chargers). A phantom fourth quarter roughing the passer penalty on Ray “Sugar Bear’ Hamilton cost the Pats the lead and the game against the eventual Super Bowl champion Raiders.

Eventually, the Pats won three titles in four years, kicking off a run of nine Super Bowl appearances in 18 seasons and collecting six Big Game wins. So any heartbreak in this era would have to be unique. A frustrating loss to the Eagles on the game’s biggest stage…it happens. Coming up short against Peyton Manning in a big game…even the astigmatic squirrel finds the acorn once in a while.

DENVER, CO - JANUARY 24: Peyton Manning of the Denver Broncos and head coach Bill Belichick of the New England Patriots speak after the AFC Championship game at Sports Authority Field at Mile High. The Broncos defeated the Patriots 20-18. (Photo by Doug Pensinger/Getty Images)
DENVER, CO - JANUARY 24: Peyton Manning of the Denver Broncos and head coach Bill Belichick of the New England Patriots speak after the AFC Championship game at Sports Authority Field at Mile High. The Broncos defeated the Patriots 20-18. (Photo by Doug Pensinger/Getty Images)

It was so utterly New England, puffed with pride, to go for the perfect season in 2007. To knock the smug grins off the faces of the 1972 Dolphins. To shut off Mercury Morris and his raps. For the nouveau riche Patriots to step right over the other franchises with multiple Super Bowl wins and say “we had the best team, evah.”

Yeah, fail.

Red Sox division

Where do 86 years of misery rank on this list? High. And often. 

The Sox no longer register on the Boston sports landscape the way they used to, and it has nothing and yet everything to do with their performance. With four championships in the past 15 seasons, they’re the Patriots of Major League Baseball. But the majority of Boston sports fans obtained their identities from this team putting them through absolute hell. 

For a gentle reminder, let’s list a few names.

Need an iconic moment for the opposing franchise? See Dent’s Fenway fly, Enos Slaughter’s “mad dash,” Tony Perez going deep, or Aaron Boone walking it off. 

How about the fanbase turning on one of their own? Think about that one for a second.

The 1946 Sox probably thought they’d be back. They weren’t. 1967 was largely regarded as a pleasant surprise, to the point where there’s probably been twice as much ink spilled on the Impossible Dream as the Cardinals team that actually popped champagne. But it also shined a flashlight on the title drought.

Game 7 in 1975 was a gut-wrenching loss on the heels of iconic moment, Carlton Fisk’s Game 6 home run. 

1978. 1986. 2003. The years continued to pile up, the city obsessed with what came to be known as the Curse of the Bambino.

BRONX, NY - OCTOBER 16: Aaron Boone #19 of the New York Yankees hits the game winning home run in the bottom of the eleventh inning against the Boston Red Sox during game 7 of the American League Championship Series on October 16, 2003 at Yankee Stadium in the Bronx, New York. (Photo by Al Bello/Getty Images)

Once the Curse was broken, the pain was different, to the point where a seven-game  defeat to the Rays in the 2008 ALCS (submarining a championship repeat) doesn’t even make the list.

Now that we have some context, what’s the top ten?

The list

10. 1976 Patriots, AFC Divisional Round Playoffs

Righteous indignation over a bad call with the team on the NFL postseason stage for the first time. A defining moment for decades.

9. 1946 Red Sox World Series

One of baseball’s all-time greats and the franchise’s signature player, Ted Williams, is denied in his only World Series appearance.

8. 1975 Red Sox World Series

Fisk put them on the cusp of the promised land, only for the rug to get pulled out. It would only get worse from here. 

7. 2019 Bruins Stanley Cup Final

More deflating than crushing, this could move up the list if it becomes the end of an era. The B’s weren’t expected to be here, but missed the open net when they got the opportunity.

6. 2010 Celtics NBA Finals

The Boston franchise with the greatest amount of hardware and least amount of torment. Game 7 was still a potent gut punch.

5. 1979 Bruins Prince of Wales Conference Finals

The end of an era and the final round of a trilogy dominated by Montreal. This was as close as they’d get.

4. 1978 Red Sox One-Game Regular Season Playoff

One of the biggest collapses in sports history, condensed into a single game.

3. 2007 Patriots Super Bowl

Pure greed. The Pats had just won three titles, but this time, they wanted it all. 

2. 2003 Red Sox American League Championship Series

The last straw. 

1. 1986 Red Sox World Series

The last straw before the last straw. 18 years of torment followed the ultimate example of snatching defeat from the jaws of victory.

Sean Sylver can be heard on 98.5 The Sports Hub. You can follow him on Twitter @TheSylverFox.