Deadspin Presents 'Heartbreak City,' to Make Fans Across North America Relive Their Worst Moments — Part 2: Two- & Three-Team Towns

Deadspin Presents 'Heartbreak City,' to Make Fans Across North America Relive Their Worst Moments — Part 2: Two- & Three-Team Towns

Illustration for article titled Deadspin Presents Heartbreak City, to Make Fans Across North America Relive Their Worst Moments — Part 2: Two-  Three-Team Towns
Graphic: 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 “two-and-three-horse towns,” cities, where there’s more than one way to crush an entire populace’s soul.

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

Advertisement

2 / 22

20. Indianapolis: 1996 AFC Championship

20. Indianapolis: 1996 AFC Championship

Soooo close ...
Soooo close ...
Photo: AP

Reggie Miller was a great player, but just as much a choke artist as the Knicks ever were (and his eight-point outburst that night was aided by an uncalled foul when he shoved Greg Anthony), and his Pacers lost to them in rather standard fashion in the 1999 playoffs, when New York was an 8 seed, Anyway, the Pacers don’t matter and nobody cares.

The Colts played second fiddle to the Patriots a fair amount during the Tom Brady years, with a lot of disappointments not only against New England, but also in Super Bowl XLIV when the Saints rallied late in the fourth quarter and a Peyton Manning pick-six made the score look a lot less close than the game actually was.

There were always high expectations with Manning, and he did deliver Indianapolis its only Super Bowl title. The 1995 Colts, on the other hand, had little such burden, squeaking into the playoffs at 9-7 before Jim Harbaugh led comebacks to beat San Diego and Kansas City on the road.

In the AFC Championship Game in Pittsburgh, the Colts again found themselves behind (in part because nobody noticed Kordell Stewart running out of bounds on a touchdown catch), and again Harbaugh rallied them, completing a 47-yard touchdown pass to Floyd Turner for a 16-13 lead with 8:46 to play. But after trading punts, the Steelers went on a big drive that included a 4th-and-3 conversion and a near-TD pass from Neil O’Donnell to Ernie Mills. Bam Morris punched in the go-ahead score from a yard out, but Harbaugh still had 94 second to work with.

Harbaugh got the Colts to the Pittsburgh 29, lofted a Hail Mary into a crowd in the end zone, and had it land right on Aaron Bailey’s chest… only to bounce away for the end of the game and the end of the Cinderella run.

Advertisement

3 / 22

19. Milwaukee: 2019 MLB Wild Card Game

19. Milwaukee: 2019 MLB Wild Card Game

undefined
Happy Juan Soto. Sad Brewers.
Photo: Getty

The Bucks won it all in 1971 with Kareem Abdul-Jabbar, and while they’ve had some other good teams, their shortcomings in the late 1970s and through the 1980s were understandable against teams like the dynasty Celtics. We’ll see what happens in the Giannis Antentokounmpo era.

The Brewers have been to only one World Series, losing to the Cardinals in seven games in 1982. That came a year after Milwaukee lost a deciding Game 5 to the Yankees in the AL East division series. The 2018 NLCS came down to Game 7, and the Dodgers beat the Brewers in Milwaukee in that one. But a big element of heartbreak that stands apart is a moment that’s not just where you get beat, but where you can’t believe that it happened like that. Enter Trent Grisham in the 2019 Wild Card game.

The Brewers took a 3-0 lead in Washington on homers by Yasmani Grandal and Eric Thames off Max Scherzer. While Trea Turner got the Nationals on the board with a homer in the third, Milwaukee was five outs away from advancing to the NLDS when Josh Hader hit Michael A. Taylor with a pitch. After Turner struck out, Ryan Zimmerman singled and Anthony Rendon walked.

Then Juan Soto singled, and Grisham overran the ball, allowing all three runners to score. Soto got thrown out on the bases, which meant the Brewers didn’t even get a chance to breathe and absorb what had just happened before they had to try to get a tying run in the ninth. They didn’t, and the Nationals didn’t just go on to the NLDS, they wound up winning the World Series that’s eluded Milwaukee ever since the Brewers got to town in 1970.

Advertisement

4 / 22

18. San Diego: 1998 World Series, Game 1

18. San Diego: 1998 World Series, Game 1

undefined
The Bamtino hits a grand slam after a questionable call on 2-2.
Photo: Getty

As far as memorable September losses in the NFL go, you can’t beat the Holy Roller, but that can’t be it. The Chargers’ playoff losses when they were in San Diego consisted mostly of blowouts. There was an overtime loss to the Jets, but that after the Chargers rallied to tie — they weren’t the ones who blew it.

In the 2006 divisional playoff, though, the Chargers did cough up a lead to the Patriots, including an interception that got fumbled away by Marlon McCree, and a game-tying 54-yard field goal missed at the end by Nate Kaeding.

That stinks, but it doesn’t stick in the craw the way that one pitch from the 1998 World Series does. No, not the fat pitch that Mark Langston served up to Tino Martinez for a grand slam, but the 2-2 pitch that sure looked like a strike.

The grand slam broke a tie in Game 1 after Chuck Knoblauch had blasted a three-run shot to erase San Diego’s lead earlier in the inning. The only other time the Padres led in the series was after the sixth and seventh innings of Game 3 before Scott Brosius hit a three-run homer off Trevor Hoffman in the eighth and the Yankees shut out the Padres in Game 4 for the sweep.

Advertisement

5 / 22

17. Tampa: 2008 World Series

17. Tampa: 2008 World Series

Rays daze. Phils thrills.
Rays daze. Phils thrills.
Photo: Getty

The Buccaneers offered some encouraging signs in the third game in franchise history, after being shut out in the first two. The defense held O.J. Simpson to 39 yards. Tampa Bay took the lead in the fourth quarter… and then Joe Ferguson hit Reuben Gant for a touchdown pass to win it for Buffalo. The Bucs wound up 0-14, then lost their first 12 games of the 1977 season before finally cracking the win column against the Saints.

Most of the Bucs’ playoff losses have been blowouts (38-0 at Dallas in the 1981 divisional round, 31-9 at Philadelphia in the 2001 wild card) or burn-the-tape craptaculars (9-0 vs. Los Angeles in the 1979 NFC Championship, 11-6 at St. Louis in the 1999 NFC Championship). The Lightning’s 2019 playoff run also was a burn-the-tape craptacular, as the team that was by far the best in the NHL, featuring the MVP and the Vezina Trophy winner, got swept by the Columbus Blue Jackets, who had never won a playoff series in franchise history. Yikes.

A few months later, the Rays were on the verge of getting swept in the ALDS, but got off the mat to clobber the Astros, 10-3, in Game 3, and beat Justin Verlander for a 4-1 win in Game 4 to bring the series back to Houston.

Heartbreak usually comes as a result of something that happens late, when seeming victory turns into defeat. In this case, it came much more quickly. Tyler Glasnow gave up three runs before he recorded an out, and with Gerrit Cole on the mound for the Astros, that was that. The next three hours were a solemn death march for the Rays, who got only two hits in eight innings against Cole, then went down 1-2-3 against Roberto Osuna in the ninth to end their season.

Does that match up to a World Series, though? Even though it was Tampa Bay’s first time in the Fall Classic, and had a “happy to be here” vibe, the Rays were tied 1-1 with the Phillies in the series and battled back from 1-0 and 4-1 deficits in Game 3 before Philadelphia loaded the bases in the ninth. Joe Maddon went to a five-man infield, and got the ground ball the Rays wanted from Carlos Ruiz, but Eric Bruntlett scored anyway and the Phillies won the remaining two games in the series.

Advertisement

6 / 22

16. Cincinnati: Super Bowl XXIII

16. Cincinnati: Super Bowl XXIII

undefined
Bengals just ran up against one of the best in Joe Montana.
Photo: AP

One way to avoid heartbreak is not to get yourself into situations where heartbreak will happen, and the Queen City’s teams have been masterful at that over the years.

The Bengals, however, did find themselves leading Super Bowl XXIII, 16-13, after Jim Breech’s 40-yard field goal. Joe Montana and the 49ers took over from their own 8-yard line with 3:04 to go, and, well, yeah, it ended up with Montana to John Taylor for 10 yards and a touchdown to cap one of the great Super Bowl-winning drives of all time.

It’s not like there’s a bad call to be angry about or someone blowing a play to live in infamy forever. The Bengals didn’t lose as much as the 49ers won, and sometimes that hurts even more, to be as good as you possibly can, and still come up against someone who’s just better.

Advertisement

7 / 22

15. Charlotte: Super Bowl XXXVIII

15. Charlotte: Super Bowl XXXVIII

undefined
This look familiar?
Photo: AP

There have been some pretty good Hornets teams, but even when they won a franchise-high 54 games in 1997, they were the lower seed in their playoff matchup with the Knicks and got swept in three games. To have your heart broken, you have to have your heart all the way into something, and that’s just never happened for Charlotte in the NBA.

In the NFL? Well, the Panthers went to the NFC title game in their second year of existence. That’s a “happy to be here” kind of thing. In the 2005 NFC Championship Game, they got flattened by the Seahawks. The other two times the Panthers have played for the conference crown, they won it, resulting in trips to Super Bowls XXXVIII and L.

Expectations were higher against the Broncos for a 15-1 team led by Cam Newton, who had an atrocious Super Bowl, going 18-for-41 with no touchdowns, a pick, and two lost fumbles. But it’s that first trip to the big game that’s got to haunt everyone forever.

The Panthers trailed by 11 points after Antowain Smith’s touchdown run at the start of the fourth quarter, but Jake Delhomme led back-to-back touchdown drives, including a very short one on which he hit Muhsin Muhammad for an 85-yard scoring pass to go up 22-21 with 6:53 left. After Tom Brady brought the Patriots right back down the field to reclaim the lead, Delhomme went 5-for-6 on the next drive, capped by a 12-yard strike to Ricky Proehl for the tie with just 1:13 left.

Could this have been the first Super Bowl to go to overtime? Well, yes, if only Adam Vinatieri hadn’t hit a 41-yard field goal, giving the Patriots their second title in three years and leaving Carolina to wonder what might have been.

Advertisement

8 / 22

14. Kansas City: 1995 AFC Divisional Game

14. Kansas City: 1995 AFC Divisional Game

undefined
Chiefs finally exorcised demon of 1996 with 2020 Super Bowl win.
Photo: AP

It doesn’t get much worse than losing the pennant on a walkoff homer in a deciding game, which is what Chris Chambliss did to the Royals in the 1976 ALCS, and it sure doesn’t help that Kansas City lost to the Yankees in the playoffs the next two years, too.

And then there’s the forever question of what if Alex Gordon had tried to score in Game 7 of the 2014 World Series, when the Royals couldn’t score against Madison Bumgarner?

Well, without Chambliss’ homer, the Royals still could’ve lost the 1976 pennant. And Gordon probably would have been out at the plate. So, those were sad moments, but nothing like the agony of the 1995 AFC divisional playoff for Kansas City.

The wind chill was 6-below, and the Colts, a dome team, came to the NFL’s loudest stadium missing Marshall Faulk. And yet... Lin Elliott missed three field goals, including a 42-yarder at the end that would have sent the game to overtime, but he’s hardly alone In the responsibility. The defense allowed an 18-play touchdown drive. Steve Bono threw three interceptions in the second half and got benched for Rich Gannon.

It would be another 20 years before Kansas City won another playoff game.

Advertisement

9 / 22

13. St. Louis: Super Bowl XXXVI

13. St. Louis: Super Bowl XXXVI

undefined
This look familiar?
Photo: Getty

Remember the 2019 NLDS, when the Cardinals went to Atlanta for the deciding Game 5 and put up 10 runs in the first inning? That was just a little bit of revenge, two decades-plus in the making, for the 1996 NLCS, when Atlanta came back from a 3-1 series deficit, starting with a 14-0 pasting in St. Louis in Game 5, continuing with an ordinary 3-1 game in Game 6, and wrapping up with a 15-0 beatdown in Game 7 — including a bases loaded triple by Tom Glavine. The Cardinals missed the playoffs three straight years after that.

But the thing is, you can’t really hurt Cardinals fans that much. Maybe if the Cubs beat them in a playoff series? Well, that did happen in 2015… and the Cardinals missed the playoffs the next three years. Still, the Cardinals have 11 world championships, and their longest title drought ever was between winning in 1982 and 2006. That time period did include Don Denkinger’s blown call in Game 6 of the 1985 World Series, which preceded an 11-0 Cardinals surrender in Game 7.

Anyway, the Rams went 14-2 in 2001, went to the Super Bowl as two-touchdown favorites, and lost on a last-second field goal to a team whose quarterback started the season as a backup and needed a controversial ruling in a snowy game in the divisional round to even get there. So much for the Greatest Show On Turf.

Advertisement

10 / 22

12. New Orleans: 2018 NFC Championship

12. New Orleans: 2018 NFC Championship

undefined
No call, no win.
Photo: Getty

The Jazz never made the playoffs before moving to Utah. The Hornets and Pelicans have had a few trips to the postseason, but only two combined trips to the second round. The 2008 Hornets did lose a Game 7 to the Spurs, and even though they had home court, it’s a kind of “what did you expect?” thing.

But the 2018 Saints were 13-3 and hosts of the NFC Championship against the Rams. They went up 13-0 in the first quarter, but the Rams clawed back to 13-10 at the half. After a trade of touchdowns in the third quarter, the Rams got even at 20-20 with 5:03 to go on a 24-yard field goal by Greg Zuerlein. And that’s when the real story began.

The Saints started moving slowly up the field, taking four plays to go 14 yards while chewing up some clock. Then Drew Brees connected with Ted Ginn for a 43-yard gain down to the Los Angeles 13. Brees threw an incompletion, Alvin Kamara had a run that went nowhere, and on 3rd-and-10, Tommylee Lewis wheeled out of the backfield and Brees threw it his way… incomplete, with no flags, even though Nickell Robey-Coleman knocked Lewis over without ever once so much as glancing in the ball’s general direction.

The Saints still took a 23-20 lead on the next play, Wil Lutz’s third field goal of the game. And if the Saints could have gotten a defensive stop, they’d have gone to the Super Bowl. But they allowed Jared Goff to drive the Rams 45 yards in eight plays, setting up a 48-yard Zuerlein boot to tie the game. Brees threw an interception on the first drive of overtime and Zuerlein won it with a 57-yard field goal.

Pinning it all on the pass interference sells short all the other ways the Saints choked. Not that it stopped anyone.

Advertisement

11 / 22

11. Montreal: 1981 National League Championship, Game 5

11. Montreal: 1981 National League Championship, Game 5

undefined
Yes, Steve Rogers, Rick Monday’s crushed baseball went thataway.
Photo: AP

First and foremost, Montreal is a hockey town, but Canadiens fans don’t get heartbroken, they get angry. Witness the Richard Riot. Taking any wrongs of hockey to be a call to civic arms remains the case into the 21st century — just ask Chris Kreider, the villain of the Habs’ most recent exit from the Eastern Conference Finals, in 2014.

The Canadiens have broken hearts far more often than they’ve had anyone inflict real emotional pain on them. In Montreal, true sadness is for baseball. The 1994 Expos, thanks to the baseball strike, never got the chance to have their hearts broken.

It was another strike season, 1981, when the Expos made their only trip to the playoffs. After beating the Phillies in the NL East division series, Montreal took a 2-1 lead on the Dodgers in the NLCS, with the last two games at Stade Olympique. Game 4 was a 7-1 drubbing as the Dodgers broke it open late, but in Game 5, Tim Raines led off the bottom of the first inning with a double off Fernando Valenzuela and came around to score on Andre Dawson’s double play ball.

The Expos only got two more hits against Valenzuela, but Ray Burris pitched eight excellent innings of his own, although he allowed the Dodgers to tie the game in the fifth on a Valenzuela groundout. In the ninth, the Expos went to the bullpen for Steve Rogers after Tim Wallach pinch-hit for Burris — and with two outs, Rick Monday hit a homer that lifted the Dodgers to the pennant. The Expos got the tying and winning runs on base in the ninth, but Bob Welch came in to get Jerry White to ground out and end the game.

They call it Blue Monday, and Montreal never got a chance to get over it.

Advertisement

12 / 22

10. Oakland: “The Immaculate Reception,” 1972 AFC Divisional Game

10. Oakland: “The Immaculate Reception,” 1972 AFC Divisional Game

undefined
Sometimes ya feel heartbreak from the tip of your toe. Or Franco Harris’ toe.
Photo: AP

Don’t let the other dramatic failures of Oakland teams distract you from the fact that the Warriors blew a 3-1 lead in the 2016 NBA Finals.

And those other failures are dramatic. Like Dennis Eckersley serving up the home run to Kirk Gibson in the 1988 World Series. The absolutely bonkers 2014 American League wild card game in Kansas City would be the pick for a lot of cities, but pales in comparison here. So, too, the Derek Jeter flip play that symbolized the just-a-bit-short results of the Moneyball era.

How about the Raiders going to snowy New England, leading all night, and winding up on the wrong end of the Tuck Rule and two Adam Vinatieri field goals through the flakes?

Those all hurt.

But it’s the Immaculate Reception.

The 1972 AFC divisional playoff was a defensive struggle, with two field goals by Pittsburgh’s Roy Gerela the only points until late in the fourth quarter. How late? The game’s first touchdown was a 30-yard run by Ken Stabler with 1:17 left. The Steelers got the ball back and started going nowhere — they faced 4th-and-10 from their own 40 with 22 seconds to go.

Terry Bradshaw got flushed out of the pocket by heavy Oakland pressure, but found what he thought was an open receiver in running back Frenchy Fuqua downfield. But as the ball got to Fuqua, so did hard-hitting Raiders cornerback Jack Tatum, and the ball deflected back in the direction from whence it came.

But there was Franco Harris, who scooped up the ball just before it hit the ground, and ran it all the way in for the touchdown. There was controversy because if the ball hit Fuqua and not Tatum, it would have rendered Harris an ineligible receiver. It took officials 15 minutes to sort it out, but they ultimately ruled that the ball did touch Tatum. Without HD and multiple camera angles, let alone instant replay as part of the rules, it’s impossible to say if they got it right, but watching it over and over again, it does appear that the ball hit Tatum’s shoulder pads, and that’s the best explanation for how it bounced the way it did. But that lingering doubt for Oakland makes the loss all the harder to live with, even half a century and two Raiders departures from town later.

Advertisement

13 / 22

9. Houston: “35-3,” 1992 AFC Wild Card Game

9. Houston: “35-3,” 1992 AFC Wild Card Game

undefined
Frank Reich out there just making history and stuff.
Photo: AP

It took until 2017 for the Astros to win a World Series, but they sure had to have liked their chances in 1986, if only they could have gotten past the Mets in the NLCS, where Mike Scott loomed in Game 7 and Houston took a three-run lead to the ninth inning of Game 6 before the Mets rallied against Bob Knepper and Dave Smith to tie the game. After forging a 4-4 tie on Billy Hatcher’s homer in the 14th, the Astros gave up three runs in the 16th… but got two runs against Jesse Orosco and had the tying and winning runs on base in the bottom of the inning before Kevin Bass struck out to end it.

The Rockets did miss 27 consecutive three-pointers in Game 7 of the 2018 Western Conference Finals, and turned a 15-point lead into a nine-point loss, but that wasn’t quite so heartbreaking because during Golden State’s dynasty, there was always a sense of inevitability, ridiculousness of the fulfillment notwithstanding.

Plus, if you want to talk about Houston blowing a lead, you’re dealing with the gold standard. It was the 1992 AFC wild card game, and having beaten the Bills in the regular-season finale, the Oilers raced out to a 28-3 halftime lead against backup quarterback Frank Reich. They made it 35-3 early in the second half. And… you know the rest. The Oilers never went to a Super Bowl before they skipped town for Tennessee. Next to that collapse in Buffalo, everything else Houston has gone through is just run of the mill disappointment.

Advertisement

14 / 22

8. Baltimore: “The Jeffrey Maier Game,” 1996 ALCS, Game 1

8. Baltimore: “The Jeffrey Maier Game,” 1996 ALCS, Game 1

undefined
Note from Deadspin Deputy Editor Rich O’Malley: I was sitting in the upper deck directly above this. I had no idea what was happening till I saw it on TV later. Yeesh, did I feel bad. But not that bad.
Photo: AP

The Ravens’ loss to the Titans in the divisional playoffs this past January was about as bad as it’s gotten since the team’s arrival, but it came with the knowledge that Lamar Jackson is just at the beginning of his career and two Super Bowls in the bank. The Colts lost Super Bowl III, sure, but they were still NFL champions that year, and the sting was soothed by winning Super Bowl V. The Orioles? Well, that’s another story. Losing the 1969 World Series as heavy favorites was a tough blow. So was Zack (then Zach) Britton being left in the bullpen in the 2016 wild card game, as Edwin Encarnacion hit the winning homer off Ubaldo Jimenez. But there’s one name that, to this day, if you bring it up to Baltimore fans, they’ll still get angry: Jeffrey Maier.

What people sometimes forget is that Derek Jeter’s controversial home run only tied Game 1 of the 1996 ALCS. Bernie Williams won it with a towering blast in the 11th. And then there was Todd Zeile’s bizarre error in Game 3. But the Maier moment defines an entire era of good but fruitless Orioles baseball.

Advertisement

15 / 22

7. Seattle: Super Bowl XLIX

7. Seattle: Super Bowl XLIX

undefined
You play to win the game. Sometimes.
Photo: Getty

The 2001 Mariners won 116 games, then got beaten so badly by the Yankees in the ALCS, they couldn’t even get the series back to Seattle for a sixth game. And they still haven’t had a playoff appearance since then. At least the 91-win 2000 team led the series against New York for a hot minute.

How bad has the Mariners’ drought been? The SuperSonics have been to the playoffs more recently, and they left for Oklahoma more than a decade ago. But that doesn’t mean the Sonics didn’t inflict some pain on Seattle while they were in town. In 1994, Seattle had the NBA’s best record, but instead of taking advantage of Michael Jordan’s absence from basketball to win their first title since 1979, the SuperSonics made a different kind of history, becoming the first No. 1 seed in NBA history to lose to a No. 8, Dikembe Mutombo and the Denver Nuggets.

But, you know, neither the Mariners nor the Sonics ever had the ball on the Patriots’ 1-yard line in the Super Bowl and decided to pass instead of handing the ball to Marshawn Lynch. That was a bad decision. Marshawn Lynch was an extremely good running back. Imagine not giving him the ball in that spot. Couldn’t be us.

Advertisement

16 / 22

6. Toronto: 1993 NHL Western Conference Finals

6. Toronto: 1993 NHL Western Conference Finals

undefined
No high-stick call, biscuit, basket, buh-bye.
Photo: AP

The Raptors finally broke through with a championship in 2019, with a run that included Kawhi Leonard hitting a buzzer-beater in Game 7 of the Eastern Conference semifinals to knock off the 76ers. That was a mirror of 18 years earlier, when Vince Carter missed a buzzer-beater in Philadelphia in Game 7 of the Eastern Conference semifinals against the Sixers.

The Blue Jays’ greatest heartbreak came amid blowing a 3-1 lead in the 1985 ALCS, as Garth Iorg, representing the pennant-winning run at the plate in the ninth inning of Game 6, struck out swinging against Dan Quisenberry.

But this is Toronto, home of hockey, and specifically of the Maple Leafs, without a Stanley Cup since 1967. And there are two candidates for the Leafs’ greatest heartbreak.

One is Game 7 of the 2013 first round in Boston, where the Leafs took a 4-1 lead over the Bruins in the third period. Final score: Boston 5, Toronto 4, in overtime.

That was bad, for sure, and for a lot of other teams, it would be easily their worst moment. But then there’s the 1993 Western Conference Finals and Kerry Fraser not calling it when Wayne Gretzky high-sticked Doug Gilmour.

Gretzky’s hat trick in Game 7 lifted the Kings to a 5-4 win and an appearance in the Stanley Cup Final, where they lost to the Montreal Canadiens. Imagine what a Toronto-Montreal final in ’93 might have looked like. Imagine what a Toronto-anyone final in any year might have looked like, because the Leafs haven’t just not won a Cup since 1967, they haven’t been to a Final since the Original Six era.

Advertisement

17 / 22

5. Pittsburgh: 1992 National League Championship, Game 7

5. Pittsburgh: 1992 National League Championship, Game 7

undefined
Look away, Yinzers.
Photo: Getty

The Steelers experience is a weird one, because the end of any season, in whatever fashion, is accompanied by the thought that the next Super Bowl is right around the corner, and they’re just about always in the mix. For that reason, the most painful thing to happen to the Steelers might just be a referee’s mistake on a coin toss on Thanksgiving that started a five-game losing streak to knock Pittsburgh out of the playoffs.

The Penguins? They did once blow a 3-0 series lead to the Islanders, back in 1975. Eighteen years later, there was David Volek’s goal to again lift the Isles over the Pens in a second-round series, this time ending a two-year run for Pittsburgh as the Stanley Cup champions.

But if you want to make a Yinzer cry, all you have to do is say two words: Sid Bream. That slide didn’t just end the 1992 NLCS, it ended the Pirates for the next two decades. Winners of three straight NL East titles, but without having reached the World Series, the Pirates saw Barry Bonds leave for San Francisco as a free agent and didn’t have a winning record again until 2013. That the wide throw to home plate was Bonds’ last act as a Pirate only makes it hurt that much more.

Advertisement

18 / 22

4. Nashville: Super Bowl XXXIV

4. Nashville: Super Bowl XXXIV

undefined
The longest yard.
Photo: Getty

It would still be easy even if Nashville had more pro sports history to draw on, but coming up one yard short on the last play of the Super Bowl is the easiest call on this entire list.

Advertisement

19 / 22

3. San Francisco: 1962 World Series, Game 7

3. San Francisco: 1962 World Series, Game 7

undefined
Bobby Richardson and Yanks celebrate.
Photo: AP

The 1990 49ers were two-time defending Super Bowl champions, and started 10-0 before losing to the Rams in November. A week after that loss, the Niners hosted the Giants, scratching out a 7-3 win on Monday Night Football. So, they knew New York had a tough defense when Big Blue came back to the Bay for the NFC Championship Game.

San Francisco had a good defense, too, maybe even better than the Joe Montana-led offense. And the Giants were without injured quarterback Phil Simms, leaving Jeff Hostetler to lead them. Expectedly, it turned out to be a defensive struggle, but Montana connected with John Taylor for a touchdown in the third quarter to make it a 13-6 game.

With the Giants down 13-9 and struggling for offense, Bill Parcells called a fake punt and Gary Reasons ran for a first down, setting up Matt Bahr’s fourth field goal of the game. It wound up coming down to one more field goal attempt at the gun, and Bahr nailed it, ending the 49ers’ dream of a three-peat.

But when it comes to the Giants breaking hearts in San Francisco, it’s of course baseball that’s the main culprit. In Game 6 of the 2002 World Series, Barry Bonds’ moonshot in the seventh inning gave San Francisco a 4-0 lead and should have been a dagger. The Giants even added another run in the seventh. But Scott Spiezio hit a three-run homer in the bottom of the inning, Darin Erstad led off the bottom of the eighth with another homer, and finally Troy Glaus doubled home the tying and eventual winning runs. The Giants did take a short-lived 1-0 lead in Game 7, but fell behind 4-1 on Garret Anderson’s bases-loaded double in the third inning and that was how it ended.

At the time, those last few outs were about as close as the Giants had come to winning a World Series since moving to San Francisco. About as close, because Game 7 in 1962 happened.

The Giants trailed 1-0 when Matty Alou led off the bottom of the ninth with a bunt single. After Ralph Terry struck out Felipe Alou and Chuck Hiller, Willie Mays doubled to right, putting the tying and winning runs in scoring position. Willie McCovey hit a screaming line drive that would have been a series winner had it gone anywhere except for where it wound up, right in Bobby Richardson’s glove. More than half a century later, San Francisco still hasn’t matched that moment for heartache.

Advertisement

20 / 22

2. Cleveland: 2016 World Series, Game 7

2. Cleveland: 2016 World Series, Game 7

Weren’t we just lamenting a Cubs loss? They finally exorcised ALL the demons by continuing Cleveland’s agony.
Weren’t we just lamenting a Cubs loss? They finally exorcised ALL the demons by continuing Cleveland’s agony.
Photo: AP

As the “Factory of Sadness,” Cleveland has been almost fortunate in its second football incarnation to be routinely awful, because the alternative is the 1980s method of getting routinely stabbed in the heart. There was Red Right 88, there was The Drive, and there was The Fumble. Oh, and there’s also Michael Jordan over Craig Ehlo to twist the knife with basketball, which also had LeBron James leaving town twice, although at least he did bring home one championship.

And it’s not like baseball has been much better. There’s a reason Cleveland is the team featured in the Major League movies. Sure, 1995 and 1997 hurt. So did blowing a 3-1 lead in the 2007 ALCS. But there was also a 3-1 lead in the 2016 World Series, and that moment in Game 7 when Rajai Davis hit the tying home run off Aroldis Chapman and it felt like destiny that this would be Cleveland’s moment. And then it rained. And then the Cubs won in 10 innings.

Shoutout to J.R. Smith for not even warranting consideration for this. That’s how bad Cleveland’s had it over the years. Losing the 2016 World Series, with so many chances to win it, after the Cavs had won the NBA title that spring and seemingly ended Cleveland’s misery… that’s the worst of the bunch.

Advertisement

21 / 22

1. Buffalo: “Wide Right,” Super Bowl XXV

1. Buffalo: “Wide Right,” Super Bowl XXV

undefined
Pretty much the defining image of sports “heartbreak.”
Photo: Getty

For a city that’s had a lot of sports suffering, there are really only two possibilities for the worst heartbreak. You know it’s rough when the Music City Miracle isn’t even in the conversation.

One is Brett Hull’s goal with his foot in the crease in triple overtime to end the 1999 Stanley Cup Final and stamp out the Sabres’ best chance at winning a championship. But as rough as that was, it was Game 6, and the Sabres, had they won it, still would have needed to find a way to win Game 7.

The Super Bowl is a one-off, and Super Bowl XXV came down to one play: a 47-yard field goal attempt by Scott Norwood. It was, of course, wide right.

The Bills returned to the next three Super Bowls and got demolished in all of them. At least that assured their place as one of the great would-be dynasties in modern sports. And you have to wonder how different it all might have been had Norwood’s kick curled through the uprights. Those other Super Bowls only add to the pain of the first.

Advertisement

22 / 22

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