Deadspin Presents 'Heartbreak City,' to Make Fans Across North America Relive Their Worst Moments — Part 3: Four-or-More Team Towns

Deadspin Presents 'Heartbreak City,' to Make Fans Across North America Relive Their Worst Moments — Part 3: Four-or-More Team Towns

Illustration for article titled Deadspin Presents Heartbreak City, to Make Fans Across North America Relive Their Worst Moments — Part 3: Four-or-More Team Towns
Image: Eric Barrow (Shutterstock)

Every year, 31 teams don’t win the Super Bowl, 30 teams don’t win the Stanley Cup, 29 teams don’t win the World Series, and 29 teams don’t win the NBA championship. There can only be one champion, after all.

Not every loser’s tale is the same, though. Sometimes, your team never has a chance. Sometimes, they exceed expectations and can view it as a success to get as close to a title as they did. Sometimes, they come up short in a way that stings, but leaves no doubt that the better team won. And sometimes… sometimes they lose in a way that makes you not want to talk about it ever again.

Well, we’re going to talk about it. We’ve split up metro areas by how many of the “Big Four” leagues they have teams in, and we’re ranking the most painful defeats each has endured, the ones that linger for years after they happened, the ones that you’d love to forget, but deep down, you really can’t.

Welcome to Heartbreak City.

Today, it’s the “four-or-more-horse towns,” cities where there are plenty of options to choose from as to how to crush an entire populace’s soul.

Sorry to all the other Jesse Spectors for ruining your Google results.

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13. Denver: Super Bowl XXIV

13. Denver: Super Bowl XXIV

Roger Craig often found this much space around him in Super Bowl XXIV.
Roger Craig often found this much space around him in Super Bowl XXIV.
Photo: Getty

There are cities where it’s hard to pick a most heartbreaking moment because there’s so much to choose from, and then there’s Denver, where… uh… er… ah… hmmm.

Sure, it’s tough for the fans anytime you lose, but… The Nuggets have hardly ever been much good, and have lost all three Western Conference Finals they’ve been to without too much drama. The Avalanche won the Stanley Cup their first year in Denver, another five years later to bookend a great run, then generally faded into obscurity and now are on the upswing again. The Rockies have been to one World Series and got swept, and their four other playoff appearances have ended before the NLCS.

Really, though, it’s a Broncos town, so we need to focus on them, and their 2-5 record in Super Bowls. That should be fertile ground, right? The scores of those five losses were 27-10, 39-20, 42-10, 55-10, and 43-8.

Let’s go with 55-10. That was the Broncos’ third Super Bowl in four years, and there was a thought that maybe this was their time after the disappointments against New York in Super Bowl XXI and Washington in XXII. It wasn’t.

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12. Detroit: 1991 NFC Championship

12. Detroit: 1991 NFC Championship

Barry Sanders and Lions couldn’t get around Washington in their only NFC title game.
Barry Sanders and Lions couldn’t get around Washington in their only NFC title game.
Photo: AP

The Red Wings were the first team to blow a 3-0 lead in a best-of-seven series in North American sports, but the 1942 Stanley Cup Final was so long ago, it’s hard to gauge how tough that was to deal with for the Motor City. Jim Joyce’s call at first base to deny Armando Galarraga a perfect game was a rough moment, but wound up making for an interesting historical footnote when the righty got his “28th out” moments later.

While the Tigers have lost their share in big spots, and the 2009 collapse was memorable, any discussion of Detroit heartbreak has to be about the team that has brought Michiganders the most angst, the historically woeful Lions.

It needs to be noted that the Lions’ first playoff appearance of the Super Bowl era, in 1970, was a 5-0 loss — yes, 5-0 — to the Dallas Cowboys. Since then, the Lions have been to the postseason only 11 times, and their only victory was in the 1991 divisional round, 38-6, over Dallas.

The next week, the Lions went to Washington for their first — and so far, only — appearance in the NFC Championship Game. And they got their doors completely blown off. Barry Sanders rushed only 11 times for 44 yards, And even though Washington managed only 17 first downs and had a 41-yard advantage in total offense, three Detroit turnovers led to a 41-10 drubbing.

“Look. If you had… one shot… one opportunity… to seize everything you wanted… in one moment… would you capture it… or just let it slip?” Wait, was that about the Lions?

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11. Philadelphia: 2002 NFC Championship

11. Philadelphia: 2002 NFC Championship

Iggles stunk up NFC Championship appearance in last game at The Vet.
Iggles stunk up NFC Championship appearance in last game at The Vet.
Photo: Getty

Each of Philadelphia’s teams has plenty to draw on when it comes to memorable moments of misery. The Phillies had their 1964 collapse and the Joe Carter home run in the 1993 World Series. The 76ers had the Kawhi Leonard buzzer beater in 2019. The Flyers had Game 7 of the 1987 Stanley Cup Final, and blew a 3-1 lead to the Devils and Eric Lindros getting clobbered by Scott Stevens in Game 7 of the Eastern Conference finals in 2000.

But Philadelphia bleeds green for the Eagles above all else, and while the Eagles do now have a Super Bowl win to their credit, they’ve also tormented their fans enough over the years for several lifetimes, whether it’s the Super Bowl in which Donovan McNabb did or didn’t vomit, Rod Martin’s three interceptions for the Raiders in Super Bowl XV, the Fog Bowl in Chicago, the blown fourth quarter lead in Atlanta in 1978

The “winner,” though, is the final game at Veterans Stadium, the 2002 NFC Championship Game. The Eagles opened the game with a 70-yard Brian Mitchell kickoff return and scored two yards later on a 20-yard run by Duce Staley… then couldn’t get a touchdown the rest of the game.

The Buccaneers took the lead at the end of the first quarter with a. 96-yard drive capped by a one-yard Mike Alstott run. By the fourth quarter, it was 20-10, but the Eagles started showing signs of life with enough time to rally. McNabb hit Todd Pinkston for 24 yards, Chad Lewis for gains of eight and 16, and Antonio Freeman for two more completions to get down to the Tampa Bay 10. A touchdown here, and the Eagles would be in position for a storybook ending at the Vet.

Instead, Ronde Barber picked off McNabb and ran 92 yards to ice the game. Cry, Eagles, cry.

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10. Miami: 1999 NBA First Round, Game 5

10. Miami: 1999 NBA First Round, Game 5

Allan Houston’s sweet stroke gave Knicks the win, after a few kisses of the rim.
Allan Houston’s sweet stroke gave Knicks the win, after a few kisses of the rim.
Photo: AP

Shoutout to the Marlins, who know how to avoid breaking hearts: by being terrible almost all the time — they’ve made the playoffs twice in franchise history and won the World Series both times. It stinks to lose the Stanley Cup in triple overtime, as the Panthers did in 1996, but that can’t be it.

Maybe the Dolphins? There’s the Snow Plow Game and the Kellen Winslow Game, yes, but the edge for Miami has to go to the Heat.

There’s a good case to be made for losing the 2011 Finals to the Mavericks, a spectacular failure to end the first year of LeBron James’ tenure in Miami, but for real heartbreak, you’ve got to go back further, to when the Heat still strived for a first title, and brought the No. 1 seed in the Eastern Conference into the 1999 playoffs.

The Heat and Knicks had fought in the 1997 playoffs, with Miami advancing to the Eastern Conference Finals. The next year, the Knicks won the last two games of the series, including Game 5 in Miami. Once again, in this first-round series, the deciding fifth game was in South Florida, and the Heat led by a point with 4.5 seconds to go. Allan Houston didn’t quite go the full Kawhi Leonard to beat the Heat, but his bouncing shot fell all the same, ending the best shot the Alonzo Mourning era Heat may have had at a title.

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9. Los Angeles: 1969 NBA Finals, Game 7

9. Los Angeles: 1969 NBA Finals, Game 7

Two all-time NBA big men battle it out over ... [checks notes] balloons?
Two all-time NBA big men battle it out over ... [checks notes] balloons?
Photo: AP

Just about the entire past decade of the Dodgers has been a study in agony, but then, there’s a rich history of baseball angst in the area, not least of all with the Dodgers and Angels undone in back to back years in the LCS by Jack Clark (bonus points to Pedro Guerrero for the glove spike) and Dave Henderson.

But Dodgers fans and Angels fans are different groups. For real unity in the area, it’s about the Lakers, with apologies to the Clippers, who maybe someday will get some love.

The Lakers have lost Game 7 of the NBA Finals to the Celtics four times, but none stands out quite like 1969, when L.A. owner Jack Kent Cooke had thousands of balloons ready to drop at the end of a series in which the home team had won each of the six games, and had flyers placed in every seat detailing the postgame plans that included the USC marching band and postgame interviews with Elgin Baylor, Jerry West, and Wilt Chamberlain.

Bill Russell, at that point a player-coach, got wind of this and read the ultimate bulletin-board material to the Celtics. During warm-ups, noting the net with the balloons hanging above the court, Russell told West, “those fucking balloons are staying up there.” And then he made sure they did, hauling in 21 rebounds as Boston, up 15 to start the fourth quarter, hung on for a 108-106 win — the first time a road team ever won a Game 7 in the Finals.

The Lakers got as close as 103-102, and had the ball, but Baylor missed a jumper and West, who was the Finals MVP in defeat, lost the ball on the next possession. Given still another chance, the Lakers tried to work the ball inside to Baylor but again turned it over. Don Nelson hit a bouncer off the back rim to get the Celtics back up by three, and the Lakers, who kept Chamberlain on the bench even after he said he was ready to return from tweaking his knee, never had another shot at the lead.

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8. Washington: 1987 Patrick Division Semifinals, Game 7

8. Washington: 1987 Patrick Division Semifinals, Game 7

Isles win at long last.
Isles win at long last.
Photo: NHL

Is it heartbreaking to lose a championship game by 73 points? Because Washington did that, at home, in 1940. It’s not just the most lopsided championship game the NFL has ever had, it’s the biggest blowout in league history. They ran out of game balls because the Bears kicked them all into the stands on extra points, so the game was finished with practice balls.

How about Game 2 of the 2014 NLDS, when Matt Williams took Jordan Zimmermann out of the game with Washington on the verge of tying the series, and instead it wound up going 18 innings, won by the Giants on a Brandon Belt homer.

Well, there’s also the Capitals, a 121-point team in 2009-10, blowing a 3-1 series lead in the first round of the playoffs against the Montreal Canadiens as they could not solve Jaroslav Halak, who had a .939 save percentage in the series.

All good options, but losing a series in a four-overtime Game 7, while the opposing goalie sets an NHL record for saves that stands for 33 years? Yeah, that’ll do it. Kelly Hrudey stopped 73 shots in the Easter Epic to lift the Islanders, a mark that stood until Joonas Korpisalo broke it in a 2020 loss to the Lightning.

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7. Dallas: Super Bowl XIII

7. Dallas: Super Bowl XIII

Oops.
Oops.
Photo: AP

There’s no doubt that the Rangers have suffered the most painful agonies of Dallas’ professional franchises. There’s David Freese in Game 6. There’s David Freese in Game 7. There’s the entirety of the seventh inning of Game 5 of the 2015 ALDS, not just the Jose Bautista bat flip, but all the awful plays by the Rangers leading up to it.

But it’s Dallas, and Dallas means the Cowboys, who… also have had a lot of heartbreak. The Ice Bowl. The Catch. Dez Caught It. It’s a tough list to sift through for America’s Team. But the most gut-wrenching moment in Cowboys history doesn’t have just two or three catchy words to go along with it.

It’s Jackie Smith, all alone in the end zone, dropping the pass from Roger Staubach that would have been the tying touchdown in Super Bowl XIII. Bless his heart, he’s got to be the sickest man in America.

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6. Minneapolis, 1998 NFC Championship

6. Minneapolis, 1998 NFC Championship

No, not him, the other Anderson kicker guy. Yeah, with an e at the end. Morton. You know, the winner.
No, not him, the other Anderson kicker guy. Yeah, with an e at the end. Morton. You know, the winner.
Photo: AP

Apologies to St. Paul, where the Wild’s arena is, but also it’s easy to forget that the Wild exists, as they’ve been to one conference final in their history and got swept. The Timberwolves at least won two games in their solitary trip to the Western finals, but even though they were the No. 1 seed in 2004, it’s hard not to acknowledge that the Kobe/Shaq Lakers were a better team. The Twins’ heartbreaks are all pretty much the same: it’s whenever they get to October and the Yankees are there.

When it comes to futility and creativity in Minnesota, it’s the Vikings. One of the great non-dynasties in the days of the Purple People Eaters, Minnesota has never had a playoff drought of more than four years in the Super Bowl era, but also hasn’t gone to the big game since the Ford Administration. That means they’ve done a lot of losing in the playoffs.

The one that takes the cake is the 1998 NFC Championship Game, when a Vikings team that had gone 15-1 held a 10-point lead in the fourth quarter against the Falcons. After Atlanta had to settle for a field goal, Minnesota had a chance to put the game away with a kick at the other end of the field, and their kicker, Gary Anderson, had been perfect all season. Of course he missed.

The Vikings still had a 27-20 lead… for the next minute and 18 seconds. That’s how long it took for Chris Chandler to bring the Falcons all the way down the field, 71 yards for the tying score.

Did the Vikings do anything with the remaining 49 seconds? No. Did the Vikings take advantage of getting the ball first in overtime? No. Did the Vikings do a damn thing with the ball when they got it back again in? No. Did the Vikings’ defense allow Atlanta to escape from being pinned inside its own 10-yard line, dinking and dunking its way up the field until Morten Andersen hit a 38-yard game winner? You betcha.

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5. Phoenix: Super Bowl XLIII

5. Phoenix: Super Bowl XLIII

Just like with Franco Harris, toes sometimes make all the difference. Santonio Holmes knows.
Just like with Franco Harris, toes sometimes make all the difference. Santonio Holmes knows.
Photo: AP

The Diamondbacks are fortunate to have given up a couple of the biggest home runs in World Series history that wound up meaning nothing, as Game 4 and Game 5 of the 2001 World Series only served to set up Game 7. It was much worse for Arizona when Todd Pratt ended their season with a walkoff homer in 1999.

The Suns couldn’t really feel too bad about losing to the three-peating Bulls in the 1993 NBA Finals. The other time Phoenix had a shot at the title was 1976, when they were on the wrong end of the triple-overtime marathon at Boston Garden.

The Cardinals have had only slightly more success as a franchise than the Coyotes, with the exception being that they actually did play for a title once, and oof, did it hurt.

Super Bowl XLIII didn’t seem like it was going to be much of a game after James Harrison’s 100-yard interception return, but the Cardinals rallied and took the lead on Larry Fitzgerald’s catch-and-run with 2:37 left in the fourth quarter. That, however, was too much time, because the Steelers came right back down the field and won the game on one of the greatest catches in Super Bowl history by Santonio Holmes.

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4. Boston: “18-1,” Super Bowl XLII

4. Boston: “18-1,” Super Bowl XLII

Manning’s arm to Tyree’s head. 18-1*.
Manning’s arm to Tyree’s head. 18-1*.
Photo: AP

First of all, let’s eliminate any Celtics stuff from consideration here. That’s a team that’s been so successful, as they lost an Eastern Conference Finals series to the 76ers, their fans cheered for Philadelphia to beat L.A. in the Finals.

The Red Sox’s moments of agony are legendary, with Game 7 losses in the World Series in 1946, 1967, 1975, and 1986 (though Game 6 of that series is more famous) — all four of their Fall Classic appearances between their victories in 1918 and 2004. There’s also Bucky Fucking Dent and Aaron Fucking Boone. But other baseball teams have had long championship droughts and suffered losses in gut-wrenching fashion.

The Bruins, meanwhile, have their own tough moments to live down: years of frustration on the wrong end of their rivalry with the Montreal Canadiens, including 1979’s infamous too many men penalty, not to mention the blown 3-0 lead against the Philadelphia Flyers in 2010. But other hockey teams have had bad calls against them and blown 3-0 series leads.

Only once, though, has a team gone to the Super Bowl with an undefeated record and lost. And the Patriots didn’t just lose Super Bowl XLII to the Giants, whom they’d beaten in the regular-season finale to finish 16-0. Frustrated all night by the Giants’ defense, they took the lead with 2:45 left in the fourth quarter on a Tom Brady touchdown pass to Randy Moss. But then Manning-to-Tyree happened. And then the touchdown by Plaxico Burress, whom Brady had openly laughed at for predicting the Patriots would only score 17 points in the game. Indeed, Burress was wrong, because the Patriots only scored 14. The Patriots won six Super Bowls with Brady, but 18-1 lives forever.

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3. New York: 1993 NBA Eastern Conference Finals, Game 5

3. New York: 1993 NBA Eastern Conference Finals, Game 5

“There, there, Charles. It’s okay. We just own your team and always will. Not your fault.”
“There, there, Charles. It’s okay. We just own your team and always will. Not your fault.”
Photo: AP

Nobody is alive who remembers Merkle’s Boner, but it needs to be mentioned, especially because at that point, New York’s baseball rivalries hadn’t really heated up yet. That’s what makes the Big Apple so tough for a moment of utter civic heartbreak. The Dodgers’ greatest heartache, the 1951 pennant race and Bobby Thomson’s homer… well, the Giants won the pennant. The Red Sox obliterating the Yankees in Game 7 in 2004, to complete their comeback from 3-0 down in the ALCS? There were plenty of Mets fans thrilled to see it.

By the same stroke, it’s impossible to pick Carlos Beltran striking out looking to end the 2006 NLCS, Trey Junkin’s bad snap, Bill Mazeroski’s home run, Dan Marino’s fake spike, the Mets’ 2007 collapse… and so many hockey moments in a three-team market whose most memorable moment is Stephane Matteau’s double-OT goal to lift the Rangers to the Stanley Cup Final and eliminate the Devils in 1994.

It’s hard to believe these days, and maybe it’s in the process of changing with the Nets in Brooklyn now, but New York can get most wrapped up all as one when it’s the Knicks. And in 1993, there was Charles Smith breaking everyone’s hearts. In 1994, there was John Starks in Game 7 of the Finals. Finally, in 1995, there was Reggie Miller’s eight points in nine seconds.

You could take any of the three, but the call is Smith, who was right there under the basket, chance after chance, unable to take down Michael Jordan and the Bulls. That play defined that rivalry and an entire generation of New York basketball, including the other heartbreaks that followed.

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2. Chicago: 2003 NLCS, Games 6 & 7

2. Chicago: 2003 NLCS, Games 6 & 7

Cubs epic collapse in 2003 wasn’t just Steve Bartman, but it was a lot Steve Bartman.
Cubs epic collapse in 2003 wasn’t just Steve Bartman, but it was a lot Steve Bartman.
Photo: AP

Say it ain’t so, Joe” is the stuff of real heartbreak, sure, but you’ve got to remember that the general public didn’t know the fix was in on the 1919 World Series as it was happening. Derrick Rose blowing out his knee in the playoffs is up there, and Cody Parkey’s doinked kick was plenty painful, but the choice for the Windy City is clear.

It’s not just the Steve Bartman play, but everything that happened afterward. Like Alex Gonzalez’s error and the rest of that inning. Then, Game 7, in which the Cubs fell behind early, tied the game on a home run by their pitcher, Kerry Wood, and took a 5-3 lead on a two-run shot by Moises Alou, the left fielder whom Bartman had stopped from making the catch in Game 6. It was all setting up as a perfect way for the Cubs to exorcise so many demons and get to their first World Series since 1945, and then the Marlins had a three-run fifth inning, tacked on another run in the sixth and two in the seventh, and that was that.

It’s a two-team baseball city, yes, but nothing in basketball, football, or hockey in Chicago measures up to the way the Cubs lost those two games and everything it meant amid a championship drought that lasted another 13 years after it happened.

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1. Atlanta: “28-3,” Super Bowl LI

1. Atlanta: “28-3,” Super Bowl LI

28-3 to 28-34. Dagger.
28-3 to 28-34. Dagger.
Photo: AP

The story of Atlanta baseball has been sweeping regular-season success followed by postseason disappointment, from the 1-0 loss in Game 7 of the 1991 World Series, to blowing a 2-0 lead in the 1996 World Series, to Eric Gregg’s strike zone in the 1997 NLCS, to Chris Burke’s homer in an 18-inning game in the 2005 NLDS, to Craig Kimbrel being left in the bullpen in 2013, to last year’s 10-run first inning for the Cardinals in Game 5 of the NLDS. But at least they won the 1995 World Series. And in that way, baseball in Atlanta has been great. The Flames and Thrashers both left, with the latter having been swept in its lone playoff appearances while the Hawks have never been to an NBA Finals, and got swept by LeBron James and the Cavaliers when they had the top seed in the East in 2015.

But none of those other Atlanta teams can even come close to the top moment of sports heartbreak for the city.

28-3.

That’s it. That’s all that has to be said.

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Sorry to all the other Jesse Spectors for ruining your Google results.