I'm going to try and put down into words about what my thoughts where I rank this loss both before and after I watch the actual broadcast and try to explain the intricacies and how I decided it.
I was born in '92. I didn't really start having any grasp of what sports actually were really until I was 7 and at that point I really only liked the Rams because they were good but, hey, the Rams are still with me in a capacity 20+ years later. So the '97 Flyers and the '93 Phillies, I didn't experience.
Like I mentioned, my initial thought was that it was outrageous to have this loss at the top of the list of worst losses in Philadelphia sports history but it did get me thinking...
The number one worst loss in city history for me will forever be Game Five against the Cardinals in 2011. We could have the absolutely most absurd way to lose happen sometime in the future and that one will still be #1 for me. It's unbeatable.
I wrote about this one at length in the Quackverse as it was my Crushing Sports Moment. We didn't want to admit it at the time but deep down when Furcal hit that triple and got knocked in we knew it was over. That Phillies team was the best team that I have ever seen in this city and probably will ever see so to see them go down in such a way will haunt me forever. It was a "what could have been?" type of thing that is a stain that will never go away. The Halladay situation that we have since learned that was spawned from that game put it into a tier that it'll never be approached to me.
Now to the hard part where thinking actually had to be done. At his very moment I honestly have to have this Eagles loss at #2 but it's not in such a way that a lot of you probably answered this question. I also have yet to see the broadcast so I very likely missed 99% of the things that happened.
The Eagles lost to an unbelievably great team. They put up a valiant effort and lost. There is absolutely no shame in that. I am not upset about that even in the slightest. This one, similar to my #1, is going to fall under the "What could have been?" category. This Eagles team was the greatest that the organization has ever put together and yet it still wasn't enough. That's sports though. The best team doesn't always win.
The thing that I am going to take away from this game and it's what is going to make it the second toughest is that we'll never know. We'll never know what would have happened if the flag was never thrown. Jalen Hurts very well may have fumbled the ball again or thrown a pick and this loss would have been rather bearable all things considered, IMO. It would fall in line with all of the other championship losses that were hard fought but the end of the day it just wasn't meant to be. Maybe for others that outcome would have made it worse.
We had the chance to see one of the all-time great Super Bowl performances go onto the pantheon of THE greatest Super Bowl performance if he and the offense were able to drive the ball down and either get a field goal to tie the game and likely send it to OT or even win it in regulation. Do they lose the game anyway? Maybe but at the end of the day we'll never know and that is so unbelievably hard to swallow.
Now I want to be clear that I am not saying that that flag cost the Eagles the game. It didn't. They had their opportunities to win the game or to put it away and they didn't because they were facing an equally great team.
I turned to my brother when the Chiefs got the ball with 5:15 left and said "they're not getting the ball back." Yes, these type of nothings are said all of the time but similar to 2011, we all likely felt that way a little bit. We were going to sit there and have our heart ripped out in slow agonizing fashion with no power to stop it.
So to see that ball fall into the end zone uncaught on third down knowing that it would provide the Eagles at least a chance to win the game and my premonition was incorrect, it was elation for only a millisecond because at the same time the flag flew across my line of vision as everyone around me was celebrating I fell down into my seat as it really was over then.
This isn't #2 because of a blown coverage (or two, Sup Corn Dog?), a fumble returned for a touchdown, a dropped pass, or an actual heart breaking single moment of finality ala a Joe Carter homer. It's because i'll never know. This game won't ever have closure for me. Yes, I know the penalty was called and the game ended so factually closure should be achievable but fandom doesn't work that way. I recognize that this isn't the first time that this has happened to the Eagles. We saw it in 2005 against the Pats but that was their own doing by running clock themselves. We saw it in 2009 but at least the Eagles still had a chance on the field to tie the game after Warner's eight minute drive.
I don't want to put it at #2 but that's where it's at the moment. As time passes on it'll likely fade and it's also probably heavily influenced by me being in the stadium for it along with it being tied to the financials of it but that's like 0.01% of the reason.
I know this is already entirely too long of a post so i'll be short here with the rest:
3: Quadruple Doink (Sixers Vs. Raptors, Game 7)
4: 2004 NFC Championship Game (Eagles Vs. Bucs)
5: ECF 2000 Blowing 3-1 Lead In Series (Flyers Vs. Devils, Game 7) (This is a personal pick)
After that my rankings would probably change on a day to day basis of where i'd put them but...
2010 NLCS Game Six - Uribe's Homer (Phillies Vs. Giants)
2010 SCF Game Six - Kane's Goal (Flyers Vs. Blackhawks)
2009 WS Game Six - Pedro/Matsui (Flyers Vs. Yankees)
2009 NFC Championship Game (Eagles Vs. Cardinals)
2004 ECF Game Seven (Flyers Vs. Lightning)
Obviously my losses are heavily skewed to the 2000's because that was my prime area of being a sports fan. As time has gone on and as priorities have changed with growing up sports don't hit the same.
TL;DR after writing all of that out, maybe this isn't actually #2 and you probably shouldn't bother reading any of that.