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The five most miserable memories as a Cowboys fan for the under-25 set

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Sometimes you have to re-live your worst moments to get over them.

NFL: Preseason-Dallas Cowboys at Seattle Seahawks Kirby Lee-USA TODAY Sports

It’s a solid guess that most of the readers of this blog are Cowboys fans. If you are not, it is nice to have you and this article is the perfect one for you to tag along on. For the majority of you who are fans of America’s Team (slight jab at you non-Cowboy fans… I had to), you are probably familiar with fans of other NFL teams having a specific disliking towards our beloved team. Perhaps it is our team’s rich history, or our owner’s propensity to keep his franchise in the spotlight. Regardless of the matter, the Cowboys seem to be at the interesting intersection of adored and loathed.

If you are a young fan of the Cowboys, say 25 years or under, the rough patches and misery of Cowboys memories actually outnumber the glory moments. Older fans lived through the glory of the 90s, and even older fans got the glory of the 70s, too. Younger fans? We’re still waiting for our time.

As a young fan, here are my five most miserable memories of being a Cowboys supporter.

5) Eagles 44 – Cowboys 6

This game happened in 2008. The reason why this game sticks out to me is that my entire family consists of Eagles fans. In my extended family, we believe in hard fun. Taunting, boasting, and antagonizing is simply a part of our competitive spirit among each other. As the youngest in my entire family, it was not an enjoyable few hours.

With a spot in the playoffs on the line, Dallas did not even come out flat. It really felt like they never came out of the locker room. Dallas was punched in the face immediately in that game. Because of the Eagles’ success within the division around that time, there wasn’t a lot of confidence for the Cowboys to come out of Philadelphia in December with a win. Once Terrance Newman opened the game with a fumble recovery, hope bubbled up. But the Eagles went on to simply trounce the Cowboys, doing so seemingly with ease.

The Cowboys were down 44-3 in the fourth quarter. They put together a decent drive to get them in position to score a touchdown and at least put a more respectful figure on the board. But the drive ended in failure, as the Cowboys came away with three points. Just imagine kicking a field goal down 44-3. And due to the unconventional final score of 44-6, that score will always live in infamy.

4) Tony Romo Intercepted by Rob Jackson

Something that goes underrated is that the Cowboys had three consecutive opportunities to make the playoffs in the last week of the season. Interestingly enough, they squandered each of those opportunities to each of the teams in the division. The reason this one hurts in particular is really due to one of my closest friends in high school being a Redskins fan.

Despite Robert Griffin III’s spectacular rookie campaign, the Redskins were far from a powerhouse. That time was really the peak of the “Tony Romo is a choker” era. I had, have, and will always back Romo. And after backing him for so long leading up to that season, he really chose to have one of his worst performances in this one, completing 20 of 37 passes for just over 200 yards and three interceptions.

3) Patrick Crayton Stops Running, Romo Intercepted by R.W. McQuarters

2007 was quite the year for the Cowboys. They seemed to really be a team destined for success. I remember feeling uncomfortable when the Giants were coming to town to face the Cowboys in the divisional round. Perhaps it was something about the way they finished that season. Regardless, it is always tricky when two teams play each other three times.

Down 21-17, the Cowboys were deep in the Giants’ territory. And because of how they had played all season, this game had the feeling of yet another cardiac Cowboys win. What ensued will always be one of the most frustrating plays in Cowboys history.

On 3rd & 11, Romo saw a seam route that could have ended in six with rotational receiver Patrick Crayton in the corner of the endzone. On the live telecast, it was said that Romo “overthrew” his receiver. But after watching replay, it is clear that Crayton stopped running.

On the ensuing fourth-down play, Romo forced a pass into double-coverage, looking to move the football past the chains. The pass was intercepted by R.W. McQuarters. With a name like that, how could you ever forget the interception? Till this day, it stills feels like the Cowboys should have won that game.

2) Romo Goes Down to Injury….. Again

The team seemed all there. Especially with how well the 2014 team played, it was a shame when Romo went down early with injury prior to the 2015 season. A terrible 2015 season gave the Cowboys an early draft pick, leading to the selection of star running back Ezekiel Elliott. With the offensive line in place, and, at the time, the combination of Romo and Elliott, it seemed like the sky was the limit for Dallas in 2016.

Then Romo opted to play in the Cowboys’ Week 3 preseason game against the Seattle Seahawks. A tackle at an awkward angle from Cliff Avril led to an uncomfortable fall from Romo. At that moment, it was almost as if the air and hype for the entire season was taken away. It seemed that the season was over before the last week of August.

It feels like an indictment on Dak Prescott, considering the Mississippi State product came right in and played spectacular at the helm of the offense. But really, this had to do with Romo and his misfortune. Romo was the guy who could bring the Cowboys to the promised land. Many will knock him for his losses in big games, but the reality is that he was the reason the Cowboys were ever competitive in the first place.

Romo was a warrior. Romo had played through multiple back problems, fractured ribs, a punctured lung, and so many other injuries in between. This Romo injury just had the feeling of the beginning of an end for the Romo era.

1) The Dez Bryant Catch/No Catch

It is a play that will always be in the minds of Cowboys fans. Was it a catch? According to the rulebook, it is now. But back then, it was not. People tend to forget about the game leading up to this play. Dallas was in a position to truly end it, as DeMarco Murray had daylight ahead of him to put the Cowboys up two possessions. Julius Peppers stuck his arm out and forced Murray to fumble the football, leading to jolt of momentum for the Packers.

Even if this play was reviewed and determined a catch, Aaron Rodgers would still have more than ample time to carve up a secondary that was spotty. But even still, anything could have happened in those last few minutes. This call gutted me for months. Even before Bryant went up for the ball, I was upset with the playcall. All season long, the Cowboys were so successful on 3rd/4th & short situations. They opted to go for the home run and unfortunately, the ball was caught on the warning track.

So there it is, Cowboys fans and BTB readers. Those are my five most miserable memories as a Cowboys fan.

Before I go get myself a drink to forget the memories, I ask you, what are your most miserable memories as fans of the Cowboys?