Deadspin Presents 'Heartbreak City,' to Make Fans Across North America Relive Their Worst Moments

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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 “one-horse towns,” cities where there’s just one major pro team to crush an entire populace’s soul, ranked from worst to worstest.

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17. Memphis: 2013 Western Conference Finals, Game 2

Zach Randolph is not pleased. Nor was the city of Memphis.

We can’t pretend that the Grizzlies have a rich and storied history here, or that they really had a chance against the Spurs in the 2013 Western Conference finals, the farthest they’ve ever gone in the playoffs, but that doesn’t mean it didn’t hurt.

The series was a sweep, but it could have played out a lot differently had the Grizzlies been able to steal one of the first two games on the road — and they nearly did, against all odds, in Game 2.

Down 83-70 with eight minutes to go, Memphis closed the fourth quarter on a 15-2 run, including the final seven points to tie the game on Mike Conley’s jumper with 18.2 seconds remaining. Tim Duncan missed a buzzer-beater, sending the game to overtime, but scored six of San Antonio’s eight points in the extra session for a 93-89 final.

The Grizzlies have been to three Game 7s, but lost each time by double digits. This was the closest that Memphis has ever been to a title, a couple of shots away from making a series of it with one of the great teams of the era. It hurts way more than an elimination game blowout.

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16. San Antonio: 2013 NBA Finals

Ray Allen’s clutch game-tying three at end of regulation kept Heat alive to vanquish the Spurs.

The Spurs don’t get a whole lot of sympathy for it, especially considering they came back and won the title the very next year, but San Antonio was eight seconds away from winning the 2013 NBA title after LeBron James’ missed three-pointer. All they had to do was grab the rebound, and the championship was theirs.

Chris Bosh came down with the ball. All the Spurs had to do was not allow a three-pointer, and the championsh— okay, you know where this is going.

Ray Allen hit that base-line three to tie the game and send it to overtime, where the Heat won it. In Game 7, Miami took the lead on Mario Chalmers’ three-pointer at the end of the third quarter, and though the game stayed close, the Spurs never did get the lead back. Kawhi Leonard missed a three with 1:26 left that would have given San Antonio the lead, Tim Duncan missed two close shots to tie in the final minute, and that was it.

The Spurs have been to the Finals five other times under Gregg Popovich, and won all five. They’ll be alright.

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15. Raleigh: 2002 Stanley Cup Final

Yes, this entire special feature is designed to make you feel just like this.

The Hurricanes don’t have a ton to draw from, and they lost the 2002 Stanley Cup Final in five games to the Red Wings, but it didn’t have to be that way, and the manner in which it unfolded was a real stinger.

After splitting the first two games in Detroit, the Hurricanes came home and took a first-period lead in Game 3 on a goal by Josef Vasicek. Igor Larionov tied things up in the second, but Jeff O’Neill restored Carolina’s lead 7:34 into the third period.

Less than two minutes stood between the Hurricanes and a 2-1 series lead, but Brett Hull scored with 1:14 to go on a deflection, with Arturs Irbe disputing that the goal should have been disallowed. There was nothing to dispute about Larionov’s goal in the third overtime, a beautiful top shelf backhand from which Carolina never recovered as they dropped the last two games by a combined score of 6-1.

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14. Jacksonville: 2018 AFC Championship

Watch out, Blake Bortles. Your moment in the sun is rapidly approaching its expiration in this photo.

When you’re up by 10 points against Tom Brady and the Patriots, in Foxboro, in the fourth quarter of the AFC Championship Game, and Blake Bortles is your quarterback, you have the right to believe that something special is happening.

You’ll wind up being wrong, because you’re the 2018 Jaguars, but you have the right to believe it.

Brady led an 85-yard touchdown drive, then a 70-yard touchdown drive. Bortles turned back into a pumpkin, and the Jaguars’ defense couldn’t get a stop on third-and-9 as the Patriots ran out the clock.

It’s a lot easier on the soul to give up 26 unanswered points the way the Jaguars did in the 2000 AFC title game.

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13. Las Vegas: 2019 NHL First Round, Game 7

Erik Karlsson (r.) set up the game-winner against the Knights.

So, the history of pro sports in Las Vegas is pretty limited, but the Golden Knights put up a collapse for the ages last year in their first-ever Game 7, which they reached after blowing a 3-1 series lead against the San Jose Sharks.

The year before, in their inaugural season, the Golden Knights became a feel-good story for Las Vegas after the mass shooting there, and their run to the Stanley Cup Final, even though it ended in defeat against the Washington Capitals, it was more heartwarming than heartbreaking. In Vegas’ second season, the Golden Knights were defending Western Conference champions, and that meant they had some expectations — which they were on their way to living up to in that series with San Jose.

The Knights were up by three goals in the middle of the third period, when Cody Eakin took a controversial five-minute major for knocking down Joe Pavelski. The Sharks scored four times on the ensuing power play, but somehow that wasn’t the end of Vegas. Jonathan Marchessault scored in the final minute of regulation to send the game to an improbable overtime, where Erik Karlsson hit Barclay Goodrow with a brilliant lead pass to set up the deciding goal.

Does this game still sting a lot without the Marchessault goal? Absolutely. Does that bit of reclaimed hope after falling behind late in the third period make the pain a million times worse? Welcome to the big time, Vegas.

(Las Vegas is now a two-team city, but the Raiders have not played a full season there yet.)

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12. Ottawa: 2003 NHL Eastern Conference Finals, Game 7

Jeff Friesen broke through with less than two minutes left in the 2003 Eastern Conference Finals.

The last few years have been pretty awful for Senators fans, watching a terrible team with a terrible owner playing terrible hockey. But it could be worse: the Senators could be good.

The first two times the Sens won division titles, in 1999 and 2001, they got swept out of the playoffs in the first round, first by the Buffalo Sabres, and then by (oof) the Toronto Maple Leafs, one of three straight playoff exits via the Battle of Ontario.

Finally free from having to play the Leafs in the 2003 postseason, a 52-win Senators team crushed the Islanders in the first round, then got past the Flyers in the conference semifinals, before meeting the New Jersey Devils to decide the Eastern Conference title.

The Senators won Game 1 in overtime, lost the next three, but came back to win Games 5 and 6 to force a Game 7, which Magnus Arvedson got started with a goal 3:33 in. The Devils got back-to-back goals from Jamie Langenbrunner in the second period, but Radek Bonk equalized early in the third.

The heartbreaker? Grant Marshall passed to Jeff Friesen, right through Wade Redden’s legs, to set up the tie-breaking goal with a little more than two minutes to go.

How is that worse than losing Game 7 of a conference final in double overtime, as the Senators did against the Penguins in 2017? Well, the 2017 Senators weren’t expected to be there, and as hard as that loss was to take, they could leave with their heads held high that they’d given Pittsburgh everything they could handle. In 2003, the Devils were a powerful foe, sure, but Ottawa had home ice, a team with expectations of its own, and let’s not forget the awful and painful couple of minutes at the end of regulation trying to find one more tying goal after New Jersey forged ahead. When Chris Kunitz scored, that game and series were just over.

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11. Calgary: 2004 Stanley Cup Finals, Games 6 & 7

Ruslan Fedotenko crushed Calgary’s soul in Cup Finals.

All those Battles of Alberta in which Wayne Gretzky was on the other side, well, those can’t hurt too much, in part because the Flames did have their share of success, reaching the Stanley Cup Final in 1986 and winning it in 1989, the first year Gretzky was out of the picture.

In 2004, it was different. The Flames didn’t have huge expectations, but they started to take on a feeling of destiny. In the first round of the playoffs, Brendan Morrison’s goal in the third overtime of Game 6 kept the Flames alive, and Martin Gelinas scored the overtime winner in Game 7 in Vancouver to complete a series that was a tour de force for Hall of Famer Jarome Iginla.

The Flames then beat the Presidents Trophy-winning Red Wings in six games, riding a hot goalie in Miikka Kiprusoff to back-to-back shutouts to close the series. A six-game win over the Sharks in the conference final gave the Flames their first shot at a Cup in 15 years, and had Calgary rocking along the Red Mile.

And the Flames had a chance to lift the Cup on home ice, where they twice rallied to tie Game 6 of the Final against the Lightning, though they should have had a tie-breaking goal by Gelinas, then had the Cup on their sticks throughout overtime until Martin St. Louis extended the series with a goal 33 seconds into the second extra session. Back in Tampa for Game 7, Ruslan Fedotenko scored a pair of goals, but Craig Conroy edged the Flames back within one, with 10:39 to go in the third period.

They’d get no closer, and haven’t been past the second round since.

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10. Oklahoma City: 2016 NBA Western Conference Finals, Game 6

When people talk about who blew a 3-1 lead in the 2016 NBA playoffs, they talk about the Finals, and Cleveland’s comeback against Golden State. And they should, but the Warriors only got to the Finals because they came back from 3-1 down against the Thunder in the Western Conference finals.

Game 6 of the series was in Oklahoma City, and with five minutes left, the Thunder had a seven-point lead. The Warriors closed out on a 19-5 run, including two of Klay Thompson’s playoff-record 11 three-pointers. The Thunder led by as many as eight points in the second half of Game 7, but fell apart in the third quarter rather than the last five minutes, which meant that it was more like having their hearts ripped out and shown to them than simply breaking.

The Thunder’s losses in the 2010 Western Conference Final and 2011 NBA Finals were tough to take, sure, as was Damian Lillard’s buzzer-beater in 2019, but there’s nothing like having victory in your hand and coughing it up.

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9. Winnipeg: 1990 NHL Division Semifinals

No Gretzky? Big problem! Dale Hawerchuk and Jets STILL couldn’t get past Oilers in 1990.

The original Jets got swept by the Edmonton Oilers in 1983, 1984, 1985, and 1987. What happened in 1986? They got swept by the Calgary Flames. In 1988? The Jets managed to take a game from Wayne Gretzky (the guy they could’ve had, which would’ve changed the landscape of hockey forever) and Co., so they lost that first-round series in five games.

After missing the playoffs in 1989, the Jets got another crack at the Oilers, now without Gretzky, in 1990, and took a 3-1 series lead. They blew a 3-1 lead in Game 5, came back from a 3-0 deficit in Game 6 only to lose 4-3, then went back to Edmonton and meekly bowed out, 4-1. Gretzky was gone, but it didn’t change anything but the number of games it took for the Oilers to dispense with the Jets.

The Jets lost a seven-game series to the Canucks in 1992 and six-gamers to Vancouver in 1993 and Detroit in 1996 before skipping town and continuing to regularly lose first-round series as the Phoenix Coyotes.

But Winnipeg got hockey back when the Atlanta Thrashers moved north, and in 2018 brought the city its first conference final.

All the Jets had to do to reach the Stanley Cup Final was knock off an expansion team, the Vegas Golden Knights. And the Jets won Game 1 on home ice… then the second-highest scoring team in the NHL in 2017-18 scored six goals the entire rest of the series, which of course ended in five games.

That hurts, but the original Jets still have the crown, at least for now, because after all those years of Gretzky’s torment, to finally be free and still lose the way they did in 1990 is just too much.

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8. San Jose: 2019 NHL Western Conference Finals

The Sharks have made the playoffs in 21 of their 28 seasons in the NHL, and having never won the Stanley Cup, that means they’ve had 21 playoff exits, each bringing a different amount of pain.

Only four of the Sharks’ playoff runs have ended with a Game 7 defeat — they’ve won eight times in the do-or-die game.

In the second round in 1994, San Jose lost 4-2 in Toronto as Wendel Clark scored in each of the first two periods. Peter Forsberg had the only goal of the 2002 Western Conference semifinal decider in Denver, in the second period. Tough to take, but the Avalanche were the defending champs. In 2013, Justin Williams, Mr. Game 7, scored a pair of second-period goals for the Kings, who won another West semifinal in which the home team won every game. Then there’s the first round in 2014, when the Sharks did score first — just as they won the first three games of the series — then the Kings came back with five unanswered goals. That’s bad. That’s real bad.

But the biggest heartbreak for the Sharks was in 2019, when they had a real “team of destiny” feel about them. A controversial penalty in Game 7 against Vegas led to four goals on a power play and an eventual overtime win. In the second round, the Avalanche had a tying goal in Game 7 overturned on review. And in Game 3 of the Western Conference finals, Erik Karlsson scored the overtime winner after a hand pass went uncalled. But the Sharks didn’t win another game, in what was their last, best chance to win a Cup with their Joe Thornton-led core.

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7. Salt Lake City: 1998 NBA Finals, Game 6

An extremely easy choice here, as Michael Jordan’s shot to win the 1998 NBA Finals towers above every other tough moment the Jazz have ever had to deal with.

The one thing that needs to be noted is that Jordan’s shot over Bryon Russell wasn’t a buzzer-beater (though did he push off?. The Jazz still had a chance to force a Game 7, but John Stockton’s shot was off the mark, and Chicago celebrated its second three-peat on Utah’s home floor.

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6. Orlando: 1995 NBA Finals, Game 1

Nick Anderson’s four missed free throws in Game 1 of NBA Finals is still hard to watch.

There are lots of examples of a series that might have been close ending after someone gagged in Game 1, like the 2017 NBA Finals after J.R. Smith’s brainfart, or the 1988 World Series after Kirk Gibson’s homer…

Or the 1995 NBA Finals after Nick Anderson’s four missed free throws.

With the Magic having a three-point lead with under 11 seconds left in the game, making just one of those free throws would have clinched the game.

The Cavaliers at least had the 2016 NBA title to fall back on. The A’s wound up winning the 1989 World Series. The Magic? Well, this was their chance. In 1996, Michael Jordan was back and the Bulls started another three-peat, including sweeping Orlando in the Eastern Conference Finals. Then Shaquille O’Neal headed to Los Angeles, and that was that.

The Magic did make it back to the Finals in 2009, only to lose in five to the Lakers. That one never felt like Orlando had a chance. In 1995, maybe they did. Maybe if Anderson hadn’t missed those shots. We’ll never know.

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5. Edmonton: 1986 Smythe Division Finals, Game 7

See that puck juuuuust about to cross the goal line? Oilers’ Steve Smith didn’t.

The Oilers won the Stanley Cup in 1984 and 1985. The Oilers won the Stanley Cup in 1987 and 1988. But the 1985-86 Oilers might have been the best team of the dynasty. They won 56 games and had four 100-point players, including Wayne Gretzky’s league-record 215, which included a league-record 163 assists.

So, what happened to this team with seven Hall of Famers? How were they undone in Game 7 of the Smythe Division finals by the rival Calgary Flames and Perry Berezan, a journeyman who scored 61 goals in 378 career NHL games, with four tallies in 31 playoff contests? Who the heck is Perry Berezan and how haven’t you heard of him being the main obstacle between the Oilers and five straight Cups?

Berezan wasn’t even on the ice when he scored the biggest goal of his career. He dumped the puck into the Edmonton zone, then headed to the bench for a line change. Oilers defenseman Steve Smith retrieved the puck behind the net, went to pass up ice… and banked it right off Grant Fuhr and into the net.

The Oilers couldn’t find an equalizer in the next 14:46, and the Flames went on to beat the St. Louis Blues in the Campbell Conference finals before losing to the Montreal Canadiens for the Stanley Cup. It’s hard to picture either of those teams having been able to handle the Oilers, who were more than 30 points better than both during the regular season. They were 30 points better than Calgary, too, but rivalries are where weird things, and heartbreaks, happen.

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4. Portland: 2000 NBA Western Conference Finals, Game 7

Blazers’ Bonzi Wells can’t watch this Shaq dunk anymore.

Game 7 of the 2000 Western Conference finals still stings so much, even in 2020, we’re getting deep dives into whether or not the NBA might have rigged it for the Lakers.

Did Scottie Pippen and Arvydas Sabonis both foul out? Yes. Did the Lakers have 37 free throw attempts to the Trail Blazers’ 16? Also yes. Did Portland have a 15-point lead in the fourth quarter and then go seven-and-a-half minutes without scoring as the Lakers tied the game? You’re damn right. The league didn’t force Pippen, Bonzi Wells, and Rasheed Wallace to miss all those shots, including both free throws by Wallace with 1:25 left and the Blazers down by two.

And then there was that memorable alley oop from Kobe to Shaq that iced the game, the clip of Shaq running and pointing after the dunk burned into Blazer fans’ brains.

Maybe the lesson is that if you’re going to lose, do it faster. The Blazers’ conference champions of 1990 and 1992 came up short against the Pistons and Bulls, but even though they lost, they get remembered fondly. Thinking about 2000 just inspires anguish about what might have been, because the trip to the Finals and a date with the Indiana Pacers were right there for the taking, and the Blazers let it slip.

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3. Green Bay: 2007 NFC Championship

Lawrence Tynes finally puts it through the uprights and sends Brett Favre packing from Green Bay.

The Packers had it all set up in Brett Favre’s final season in Green Bay. They went 13-3, blew out the Seahawks in the divisional round, and got to host the NFC title game at Lambeau Field, where they were 5-0 all-time in NFL and NFC championship contests.

It was Ice Bowl-level cold that night in Wisconsin, but Favre heated things up with an early 90-yard touchdown pass to Donald Driver. The Packers trailed at the start of the fourth quarter, but Mason Crosby’s 37-yard field goal tied things up to set the stage for late drama.

Lawrence Tynes missed a 43-yard field goal on the Giants’ next drive, but the Packers couldn’t capitalize, going three-and-out. The teams then traded punts, putting the ball in Eli Manning’s hands with 2:15 left. And Manning got the Giants down inside the 20, setting up Tynes for a shot at the game-winner from 36 yards — which he missed.

In overtime, the Packers got the ball, and having been let off the hook by a pair of Tynes misses, this was their moment. Only Favre threw a floater that Giants cornerback Corey Webster picked off. The Giants only advanced the ball five yards in the next three plays, leaving Tynes to try a field goal from 47 yards after missing two shorter kicks. This time, though, the Scottish kicker booted it through the uprights, and through Green Bay’s collective heart to end Favre’s time as a Packer.

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2. Vancouver: 1994 Stanley Cup Finals, Game 7

The pick for the Canucks is a matter of which kind of Game 7 defeat feels worse.

In 1994, Vancouver forced a Game 7 against the New York Rangers after having trailed the Stanley Cup Final, 3-1. Back at Madison Square Garden, the Rangers took a 2-0 lead in the first period, but Trevor Linden’s shorthanded goal got Vancouver back within one. After Mark Messier made it 3-1 at the end of two, Linden scored on a third-period power play to make it a one-goal game for the final 15:10. But that was how it stayed, despite furious Canucks attempts to find an equalizer against Mike Richter. The Rangers won their first Stanley Cup in 54 years. The Canucks continued to wait and the city of Vancouver rioted.

In 2011, meanwhile, the Canucks brought a 3-2 lead to Boston for Game 6, where the Bruins knocked out Roberto Luongo with three goals on eight shots in the first 8:35. It didn’t get much better with Cory Schneider in net, and Boston rolled to a 5-2 win. But the Canucks still had a home game in their pocket… which went horribly. Patrice Bergeron and Brad Marchand scored two goals apiece, Tim Thomas made 37 saves, the Bruins lifted the Cup and the city of Vancouver rioted.

The 2011 Canucks were the best team in the NHL, in the midst of a four-year run of 100-point seasons, and coughed up multiple chances to win the Cup. The 1994 Canucks were a mere game over .500, a Cinderella story through the playoffs, and had to rally just to get in position to have a chance at a Game 7, let alone to have a chance to send that game to an overtime that never came.

You get into a team like the ’94 Canucks, growing in belief with each step along the way that it’s meant to be. With a team like the ’11 Canucks, you’re invested, but the emotions are different. When a team like that loses, it’s a letdown. When a team like the ’94 Canucks loses, that’s a heartbreaker.

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1. Sacramento: 2002 NBA Western Conference Finals, Game 6

Just because this is one of the easiest picks doesn’t mean it hurts any less. The Kings have been mostly bad since arriving out west from Kansas City in 1985 — they have more playoff appearances in years where they had a losing record (two) than appearances in the Western Conference finals (one).

But, oh, that one.

It was 2002, and the Kings had the top seed in the West and a 3-2 series lead over the two-time defending NBA champion Lakers. Whether or not the NBA rigged it for the Lakers (and even Chris Webber hasn’t let that idea go), the way that Game 6 unfolded was atrocious. With the Lakers up 103-102 and 11.8 seconds left, Kobe Bryant absolutely trucked Mike Bibby, throwing an elbow right to his face, bloodying the Sacramento guard’s nose. It wasn’t called for anything, and instead drew a foul from Doug Christie.

Kobe made both free throws — two of 27 that the Lakers got to shoot in the fourth quarter to Sacramento’s nine — and Bibby, with gauze up his nose, missed a tying three at the other end.

The Kings did send Game 7 to overtime after Bibby, fouled by Bryant, made two free throws. But in the extra session, the Kings shot 3-for-12, Shaquille O’Neal scored six of Los Angeles’ 12 points, and that was that. The Lakers went back to the Finals and won again, and while the Kings had another couple of good years with that core, they lost seven-game, second-round series the next two years to the Mavericks and Timberwolves.

Deadspin Presents 'Heartbreak City,' to Make Fans Across North America Relive Their Worst Moments — Part 1: One-Team Towns

Deadspin Presents 'Heartbreak City,' to Make Fans Across North America Relive Their Worst Moments — Part 1: One-Team Towns

17. Memphis: 2013 Western Conference Finals, Game 2

17. Memphis: 2013 Western Conference Finals, Game 2

16. San Antonio: 2013 NBA Finals

16. San Antonio: 2013 NBA Finals

15. Raleigh: 2002 Stanley Cup Final

15. Raleigh: 2002 Stanley Cup Final

14. Jacksonville: 2018 AFC Championship

14. Jacksonville: 2018 AFC Championship

13. Las Vegas: 2019 NHL First Round, Game 7

13. Las Vegas: 2019 NHL First Round, Game 7

12. Ottawa: 2003 NHL Eastern Conference Finals, Game 7

12. Ottawa: 2003 NHL Eastern Conference Finals, Game 7

11. Calgary: 2004 Stanley Cup Finals, Games 6 & 7

11. Calgary: 2004 Stanley Cup Finals, Games 6 & 7

10. Oklahoma City: 2016 NBA Western Conference Finals, Game 6

10. Oklahoma City: 2016 NBA Western Conference Finals, Game 6

9. Winnipeg: 1990 NHL Division Semifinals

9. Winnipeg: 1990 NHL Division Semifinals

8. San Jose: 2019 NHL Western Conference Finals

8. San Jose: 2019 NHL Western Conference Finals

7. Salt Lake City: 1998 NBA Finals, Game 6

7. Salt Lake City: 1998 NBA Finals, Game 6

6. Orlando: 1995 NBA Finals, Game 1

6. Orlando: 1995 NBA Finals, Game 1

5. Edmonton: 1986 Smythe Division Finals, Game 7

5. Edmonton: 1986 Smythe Division Finals, Game 7

4. Portland: 2000 NBA Western Conference Finals, Game 7

4. Portland: 2000 NBA Western Conference Finals, Game 7

3. Green Bay: 2007 NFC Championship

3. Green Bay: 2007 NFC Championship

2. Vancouver: 1994 Stanley Cup Finals, Game 7

2. Vancouver: 1994 Stanley Cup Finals, Game 7

1. Sacramento: 2002 NBA Western Conference Finals, Game 6

1. Sacramento: 2002 NBA Western Conference Finals, Game 6