Dallas Cowboys Choke in the Playoffs Again! Most Painful Loss Ever?

​So, as a lifelong Dallas Cowboys fan, I have been asked multiple times if the recent playoff loss to the Green Bay Packers was the most painful loss ever. It was certainly agonizing to watch them get beat to a pulp, but I would not rank it as the most painful playoff loss. I would, however, rank the game as the most EMBARRASSING playoff loss for the Dallas Cowboys!

Honestly, the loss would have been more tragic if Dallas was the heavy favorite to win the Super Bowl, but they were not. Not even close. I’m as loyal as they come, but even I have to admit that beating the Detroit Lions, and then beating the San Francisco 49ers at their home stadium, and THEN beating the AFC champion in the Super Bowl, would have been an extremely high task for Dallas. They had difficulties in beating quality opponents in the 2023 season. Though not impossible, the chances of beating quality, top-tier teams three consecutive weeks almost seemed unrealistic for Dallas.

So what was the most painful playoff loss for Dallas? Well, keep in mind that I was not a full-fledged NFL fan until around the year 1985, so I can’t include the game in which Dallas lost to the 49ers in the 1981 NFC championship, which is forever famous for “The Catch” by Dwight Clark in the back of the end zone to break Cowboys’ fans’ hearts.

During MY time of viewing Dallas (1985 to Present), I can easily say the most painful playoff loss was in 2007 against Eli Manning and the New York Giants. During the 2007 season, Tony Romo led Dallas to a 13-3 record and a #1 playoff seed. Keep in mind that one of those three losses was the last game of the regular season, taking place after Dallas had already clinched the #1 seed, so many starters were not playing that game that was essentially meaningless.

Romo was on fire that year! He became the first Cowboys quarterback to throw for over 4,000 yards. Watching Romo, Terrell Owens, Marion Barber, Jason Witten, and all of the other talent on that team was a thing of beauty week after week! Dallas was undoubtedly a heavy favorite to go to the Super Bowl. It was already a foregone conclusion by many that Dallas would be there.

Dallas was a high-scoring team that had already beat the Giants two times during the regular season. There was no reason to think the result would be different in the divisional playoffs against New York, although some say the hardest thing to do in the NFL is to beat the same team in the NFL three times in the same season. Well, I guess that was proven to be correct!

As many Cowboys fans know, Dallas lost that game by a score of 21-17. To get eliminated early in the playoffs as a mid-tier favorite for the Super Bowl is difficult, but losing as a HEAVY FAVORITE is downright excruciating! Romo deserved a shot at the trophy and this was his arguably his best chance. This game gives me nightmares, especially certain plays that could have changed the game dramatically! 

Whenever I hear the name of Patrick Crayton (Wide Receiver), I automatically think of a play with about a minute left in the 3rd quarter of that game in which he DROPPED a perfectly thrown pass on a 3rd and 14 from deep in their own territory. It would have been at least a 30-yard gain, if not more. They then had to punt and give the Giants the ball back with good field position. Things went downhill after that. To make matters worse for Crayton, he missed another big opportunity when he randomly pulled up momentarily during a fade route to the end zone with just seconds left in the game. The throw ended up being overthrown, but likely only because Crayton slowed down! Should have been a touchdown! Thanks for the memories, Patrick!

So, yes, the Cowboys giving up 48 points to the Packers was hard to handle, but the 2007 playoff loss to the Giants will always be the most painful one for me!

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