Top 15 Most Embarrassing Moments in Dallas Cowboys History

The Dallas Cowboys are quite possibly the most polarizing franchise in all of professional sports. In the 1990s they were dynamite with Tory Aikman, Emmit Smith, Michael Irvin, and a stellar defens

The Dallas Cowboys are quite possibly the most polarizing franchise in all of professional sports.

In the 1990s they were dynamite with Tory Aikman, Emmit Smith, Michael Irvin, and a stellar defense. Before that, Roger Staubach brought many great memories to Cowboys fans. Things were good.

Recently, things haven't been as pleasant. While the Cowboys have still managed to have ultra talented teams, the hardware has been absolutely no where in sight. Jerry Jones had some pretty spectacular seasons as owner in the early years, but of late he has everyone scratching their heads. Most recently with the disturbing signing of Greg Hardy.

Make no mistakes about it, Tony Romo is one of the most talented quarterbacks to ever step foot on the field. The film and stats tell the whole story. He has game.

That clutch gene. The one that quarterbacks such as Tom Brady, Ben Roethlisberger, and Eli Manning possess. Romo missed out on this gene.

It seems as if every year fans have so much hope for Romo, he plays great for most of it, and than finds a way to crack under the pressure at the worst times.

In 2015, Romo didn't get the chance to choke, as he only played two full games as the Cowboys had a disastrous 4-12 season. Still, Jason Garrett remains head coach, and Jerry Jones is, as always, confident the team can turn it around.

Here's a stat that will make any Cowboy fan cringe. Since the Jacksonville Jaguars entered the league in 1995, they have more playoff wins than the Cowboys. The Jaguars have been the laughing stock of the league, so that one has to hurt.

With that, we countdown the Top 15 Moments in Cowboys history.

15 Tashard Choice asks Michael Vick for autograph following Monday Night Loss

The Dallas Cowboys had just suffered its ninth loss of the season to the Philadelphia Eagles on Monday Night. Tashard Choice made it an even more embarrassing night when the players met at midfield.

With all the camera men crowded around, Choice thought it would be a good idea to ask Eagles quarterback Mike Vick for his autograph. And sure enough, the cameras caught every second of it. Of all the teams to do this against, he picked the division rival Eagles?

14 Tony Romo's Short Lived 2015 Thanksgiving Day

Tim Heitman-USA TODAY Sports

Tony Romo broke his collarbone in week two against the Philadelphia Eagles, and the Cowboys were hopeless without him. Then he returned for a road bout with the Miami Dolphins and won to improve the Cowboys to 3-7.

This began talks of Romo running the table and taking Dallas to the playoffs. People were actually beginning to think this could be a real possibility. The next game would be at home against the 10-0 Carolina Panthers. Shockingly the Cowboys were favorites.

They didn't look like favorites, as Romo threw two pick sixes in the first quarter, re-broke his collarbone in the second half, and the Cowboys got blown away. Season over, in awful fashion.

13 Tony Romo Hands the Lions a Comeback Victory


The Dallas Cowboys were running away with a game on the road against the Detroit Lions in 2013. The score was 27-3, and well in hand.

Matt Stafford and company couldn't move the ball one bit on offense. However, two late pick sixes by Tony Romo opened the door for Detroit, and Dallas suffered an unbelievably embarrassing loss.

12 Tony Romo Forgets the Down

The Cowboys trailed by seven late in the game against the Denver Broncos in 2009. Tony Romo spiked the ball on second down to kill the clock, and than threw incomplete on third and fourth down.

When the defense came out onto the field, Romo yelled at them to go back. Based on how he handled the following downs, and how he reacted once he failed to convert, it was pretty clear that Romo neglected the second down spike and thought the last play was on third down. That's not what you want from your star quarterback.

11 Tony Romo Can't Connect with a Wide-Open Miles Austin


The Dallas Cowboys had the path to the divisional title made into a home game against the New York Giants in in December of 2011.

In the fourth quarter, Miles Austin broke free down the field for what would be a sure touchdown, and Tony Romo couldn't connect with him. It looked like Austin may have lost it in the lights. Either way, it was a patented Cowboys loss.

10 Jerry Jones Refused to Pay Emmitt Smith


In 1993, Jones thought it would be a smart move to not pay Emmitt Smith the money he deserved. Despite him being a vital part to back-to-back Super Bowls, the owner wagged his finger at one of the most talented backs in the game.

Smith held out and waited. It's unclear why he waited to pay the man, but when the Cowboys lost the first two games, reality struck and Jones gave Smith a four year deal worth $13 million a year.

9 Jerry Jones Signs Greg Hardy

Kim Klement-USA TODAY Sports

The fact that Greg Hardy isn't rotting in a jail cell for his domestic abuse case is beyond disturbing. There is absolutely no place for him in the NFL.

But, oh wait. Jerry Jones says otherwise. The Cowboys didn't care how terrible of a person Hardy was, all they cared about was that he could sack the quarterback. Fans should be ashamed and up-in-arms about the fact that Dallas decided to sign such scum to their team. Even worse for Jones is the fact that Hardy didn't help the lost cause of a season, as the team finished just 4-12.

8 Cowboys Get Blown Away by Eagles in Win-and-In Game

It was Sunday night, and a win would put Tony Romo and the Dallas Cowboys into the postseason.

But the game was over before it even started. The boys got absolutely torched, losing 44-6. Not the performance you want to see with the regular season on the line.

That was one of three win-and-in games that were botched in the Romo era. Not a good statistic for a franchise quarterback.

7 Dave Campo's Tenure as Head Coach


Dave Campo coached the Dallas Cowboys for three seasons, with 2002 being his final. In those three seasons the team went 15-33, never had a winning season, and never made the playoffs. He was the only coach in Cowboys history to have neither.

It was a horrid three seasons, and a period of time the Cowboys and their fans would love to forget about as clearly Dave Camp is not a pleasant memory for anybody who follows the storied organization.

6 Tony Romo Takes Vacation with Jessica Simpson Before '08 Playoffs


A week before the Cowboys Divisional Playoff game against the New York Giants in 2008, Tony Romo decided to take a trip to Los Cabos with his then girlfriend Jessica Simpson.

This was arguably the most talented Cowboy team in the past decade or so, and Romo decided that it would be a good idea to vacation right before the big game. The Cowboys had the number one seed, and all the expectations in the world, and a week before, he was probably relaxing and laying out in the sun. A real Johnny Manziel move.

To make matters worse, Romo struggled and the Cowboys lost.

5 The infamous Leon Lett Fumble

The Dallas Cowboys were well on their way to defeating the Buffalo Bills in Super Bowl XXVII. But before the confetti fell, Dallas still somehow managed to do something totally embarrassing.

The Cowboys forced a Jim Kelly fumbled, which defensive lineman Leon Lett scooped up. He looked destined to score, but for some reason decided to hold the football out and showboat his way across he goal line. A Buffalo Bill was hustling behind and managed to slap the ball away and make Lett look really, really dumb.

If Dallas lost, this would be number one. EASILY.

4 Terrell Owens Cries for Tony Romo

When the Dallas Cowboys dropped the Divisional Playoff game at home against the New York Giants, the media immediately asked questions about quarterback Tony Romo. Rightfully so, as the Cowboys star struggled all game long.

Terrell Owens didn't like that one bit. In fact he spurted tears in the post game press conference, and was on camera when he infamously said, "that's my quarterback." Hilarious, sad, ridiculous. There are many words that can be used to described the strange reaction by Owens.

It did seem genuine, though. Regardless, it didn't make the loss any easier for Cowboys fans to bear.

3 Jackie Smith's Drop in Super Bowl XIII

If this drop was game-deciding, it would surely be sitting up at number one.

Down 21-14 against the Steel Curtain, on a third-and-three, Roger Staubach found tight end Jackie Smith all alone in the endzone, completely wide open and uncovered, and it bounced off his chest and fell to the ground.

The Cowboys went on to lose 35-31 as Terry Bradshaw and the Pittsburgh Steelers would take home the Lombardi Trophy.

2 Leon Lett's Thanksgiving Day Blunder

It's difficult to make a list like this multiple times as a defensive lineman, but Leon Lett found a way.

On Thanksgiving Day in 1993, the Miami Dolphins attempted a 41 yard game-winning field goal against the Dallas Cowboys. Trailing 14-13 in the snowy conditions, the odds were in the Cowboys favor.

The odds got even better when the kick was blocked and fell short of the endzone. In fact, everyone thought the game was over. Enter Leon Lett.

Lett, for some reason (which no one but him will ever know) jumped onto the football, pushing it into the endzone where the Dolphins fell on it for a game-winning touchdown. There was no excuse or reason for the play Lett made.

Dallas did win the Super Bowl that season, but this play will always go down as one of the Cowboys all-time worst.

1 Tony Romo's Botched Snap in Wildcard Loss to Seahawks

This might take the cake as the most embarrassing moment in Dallas Cowboys history. Any Dallas fans reading this has to be cringing, as it must be firmly in their minds forever.

Trailing 21-20 in a 2006 Wildcard Game vs. the Seattle Seahawks, the Cowboys were attempting a game-winning last minute field goal. Starting quarterback Tony Romo was the holder. Game over? Right?

That's what the home crowd thought. But in an epic fail, Romo botched the hold, then attempted to run for the endzone and was tackled at the one. The image of Romo grasping his facemask at the goal line will never go away.

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Top 15 Most Embarrassing Moments in Dallas Cowboys History