Philadelphia Sports can be a lot of fun. As a city, we have shared many great moments. With all that fun though, comes heartbreak. Much of our sports-watching life has been heartbreaking moments. Even with our teams actually being better this century, that has only made the eventual heartbreak that much worse.

Heartbreak only happens when you love something enough in the first place. When your team just sucks, you can’t get your heart broken. It may be soul-crushing watching them lose year after year. But you never get your spirits up enough to have your heart broken. If your team is good, and you start to think you can maybe they can win it all, that is when true sports heartbreak can happen. And especially in recent history, we have been put through it.

Since the Eagles did win it all in 2017, we have seen 3 of our teams get to their respective championship game. The Eagles made it back in 2022. The Phillies got all the way to the World Series before that. And the Union were in the MLS Cup at the same time as the Phillies were on that run.

All of them lost. Not to mention the Sixers have broken our hearts with 2nd round exits 5 times just in the Joel Embiid era. The Flyers haven’t been good enough to break our hearts in that time. The only one that could maybe be heartbreaking was their collapse in the Covid Bubble after looking so good early on.

While it may hurt to re-live the past, it is also part of the healing process.  So let’s look at some of the most heartbreaking moments from our past. The times our teams came so close, just to fall apart in the very end.

Here are 7 of the most heartbreaking moments in Philadelphia Sports History:

• Joe Carter Walks It OFF

  When this happened, I wasn’t even 1 yet. So I didn’t experience the heartbreak myself. But I have talked to people who did. Just the mention of it to them changes the atmosphere of the room. For such a magical run to end like that? I get it. If that happened now I don’t think I would ever recover.

• The Quadruple Bounce

  This was my Joe Carter moment. I was so sure this Sixers team would win it all. And then in an instant, the run was over. It genuinely felt like time slowed down while that ball was bouncing. And it just had to bounce into the net. Maybe if it bounced out, the Sixers would have won in OT, and gone on to win it all. But it was not meant to be. And this wound up being the last game Jimmy Butler played for the Sixers, making it even more painful.

• James Bradberry Called For Defensive Holding

  PFF on Twitter: "James Bradberry owns up to the late defensive holding penalty pic.twitter.com/g5TUXhU2jO / Twitter"

  James Bradberry owns up to the late defensive holding penalty pic.twitter.com/g5TUXhU2jO

  Whether you believe it was holding or not, this was the moment the Eagles lost the Super Bowl. If they had gotten that stop, the Chiefs would have kicked an FG and gone up by 3, and Jalen Hurts would have gotten the ball back with time. Given how Hurts was playing, there is a real chance he would have either won the game or at least forced OT. Instead, the Chiefs were able to run out the clock even more. All Hurts had time for was a Hail Mary. We were robbed of a chance at seeing if Hurts had what it takes to march down the field for a game-winning TD.

• Ben Simmons Doesn't Dunk It

  This one hurts not just because it killed their chances of winning that season, but because of what it represented for the future of the franchise. It was the end of the Ben Simmons era. Him not dunking it the was the final straw. He never played another game in Philly. And now is one of the most hated players by Philly fans. He went from team savior, to a pariah. people give Sixers fans hard time for how they reacted. But they never mention how supportive we were leading up to that moment. We defended the guy harder than any other fan base would. But the pass, and his subsequent quitting, was too much for us to forgive.

• 1 Bloody Nil

  Gateway Grinders on Twitter: "The Cardinals face the Phillies in the postseason for the first time since 2011 Game 5.In one of the best pitching duels you'll ever see, Chris Carpenter bested the late great Roy Halladay in a 1-0 shutout. #stlcards pic.twitter.com/PLiZD1VcaR / Twitter"

  The Cardinals face the Phillies in the postseason for the first time since 2011 Game 5.In one of the best pitching duels you'll ever see, Chris Carpenter bested the late great Roy Halladay in a 1-0 shutout. #stlcards pic.twitter.com/PLiZD1VcaR

  This one hurt for so many reasons. I remember just watching the game in the common area of my dorm freshman year. This was the best Phillies team I have ever seen. Over 100 wins in the regular season. One of the better pitching staffs ever assembled. And they couldn’t get past the first round. Chris Carpenter shut them out in game 5 to end the Phillies season. Worse yet, Ryan Howard suffered an injury that derailed his career. It took over a decade for the Phillies to get back to the playoffs.

• Eagles Lose To The Bucs in 2002

  Ari Meirov on Twitter: "The #Bucs will celebrate Ronde Barber's induction into the Hall of Fame in Week 3 when they host the Philadelphia Eagles on MNF.Barber's 92-yard pick-6 vs. the Eagles in the 2002 NFC Championship game is one of the most iconic moments in team history.pic.twitter.com/ds4vAAC5nW / Twitter"

  The #Bucs will celebrate Ronde Barber's induction into the Hall of Fame in Week 3 when they host the Philadelphia Eagles on MNF.Barber's 92-yard pick-6 vs. the Eagles in the 2002 NFC Championship game is one of the most iconic moments in team history.pic.twitter.com/ds4vAAC5nW

  Is it weird if this one hurts more than the Super Bowl loss two years later did? It felt like this was their year. Everyone had them beating the Bucs. And then it would have been the Raiders waiting for them, that year, not the Patriots. But they blew it again in the NFC Championship game. All capped off by the Ronde Barber pick 6. This may actually be the first time I had my heart broken in Sports.

• Patrick Kane Wins It In OT

  The 2010 run to the Stanley Cup was some of the most fun moments watching sports in my life. You couldn’t write it any better than it happened. The Bruins series to get there was as dramatic as it gets. They go down 3-0 in the series, but then even things up. Then they go down 3-0 in game 7, but come back to win it. If you put that in a movie people would call it too cheesy. But it happened. Then they sputtered out. The nail in the coffin was Patrick Kane’s game winner in OT of Game 6. The Flyers have yet to get close to a Stanley Cup since 2010. The wait to see if the goal was actually good made it even worse.

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