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ARLINGTON, TX - NOVEMBER 27: Tony Romo #9 of the Dallas Cowboys passes against the Philadelphia Eagles in the second half at AT&T Stadium on November 27, 2014 in Arlington, Texas.

It is Dallas week. Cowboys vs Eagles. It’s the first matchup we circle on the schedule every single year. The time all the loser fans who grew up in South Philly but for some reason root for the Cowboys crawl out of their holes to puff their chest out. This Sunday the Cowboys come to town for the team’s first matchup this season.

It is really the only thing Dallas fans have to look forward to since we know they won’t win anything come playoff time. They have just 5 playoff wins since 1996. Nearly 30 years, and 5 wins, none of which came in the 2nd round. The Eagles meanwhile have more to look forward to. I was 3 the last time the Cowboys actually won anything. In that same time, the Eagles have not only been in the playoffs nearly every season, but they win when they get there. 16 playoff wins, 1 Superbowl win, 3 Super Bowl Appearances, and 7 NFC Championship appearances. Losing in the Conference Championship that many times hurts, but being as irrelevant as the Cowboys would hurt way more.

Still, even though they have had zero relevance in the past 20+ years, we all still hate them. Maybe it is because their local fans are the most annoying people on the planet. Or maybe it is because the National Media still treats them as the best team ever even if they haven’t won crap this century.

But which Cowboys do we hate the most? Whose face makes us cringe just by appearing on our TVs? In honor of it being Dallas week, let’s look at some of the Cowboys we hated the most. From the current team, through the Tony Romo years, the Troy Aikman era, and all the way back to when it was Roger Staubach.

Here are 11 Cowboys Players We Loved To Hate:

 

  • Dez Bryant

    GREEN BAY, WI - JANUARY 11: Dez Bryant #88 of the Dallas Cowboys attempts a catch over Sam Shields #37 of the Green Bay Packers during the 2015 NFC Divisional Playoff game at Lambeau Field on January 11, 2015 in Green Bay, Wisconsin. Initially ruled a catch, the call was reversed upon review.

    (Photo by Mike McGinnis/Getty Images)

    For one, Dez Bryant was pretty damn good when he was with the Cowboys and was a consistent source of annoyance in Eagles-Cowboys games. But he is also just an obnoxious person. Between his on-field and off-field antics, he made it easy to hate him. Also, just a reminder, Dez didn’t catch it.

  • Tony Romo

    ARLINGTON, TX - NOVEMBER 27: Tony Romo #9 of the Dallas Cowboys passes against the Philadelphia Eagles in the second half at AT&T Stadium on November 27, 2014 in Arlington, Texas.

    (Photo by Ronald Martinez/Getty Images)

    Not only did we have to deal with him as a player, with the media gushing over him even though he never actually won anything. But now we have to deal with him on CBS every week. Thankfully people are finally coming around on him kind of sucking as an announcer, because the whole predicting plays thing went out the window as he got further out of the league and more out of touch with what NFL teams are doing.

  • Deion Sanders

    8 OCT 1995: DALLAS CORNERBACK DEION SANDERS ON THE SIDELINE DURING THE COWBOYS 34-24 VICTORY OVER THE GREEN BAY PACKERS AT TEXAS STADIUM IN IRVING, TEXAS.

    Mandatory Credit: Al Bello/Allsport

    Deion is a weird one. Because with all of his bluster, part of me actually likes him. Like if he was an Eagle, or even anything other than a Cowboy, I would probably love him. But him being so loud, and also a Cowboy, you can’t help but hate him. It doesn’t help he is constantly in the news because of his job at Colorado. And I still can’t get over him making the media members call him Coach. There is a level of ego there when you need other grown men to call you, another grown man, coach.

    Shoutout to Jason Garret who also told reporters to call him coach when he was the Giants Offensive Coordinator. Garrett almost made this list, but then I decided him being such a bad coach was a good thing for the Eagles, so I don’t hate him. Deion Sanders was a Hall of Fame Player and looks like a good coach, so he is actually worth hating.

  • Michael Irvin

    Dallas Cowboys wide receiver Michael Irvin competes in a flag-football legends game during 2005 Pro Bowl week in Ko Olina, Honolulu February 11, 2005.

    (Photo by Al Messerschmidt/Getty Images)

    He was annoying as a player because he was a Hall of Fame Wr who played for the enemy. But as a TV Personality he is somehow worse. The guy is everywhere. We constantly have to hear his take on everything, and his takes are never that good or interesting. They will push him even more this week, and he will have a ton of bluster about the Cowboys, even though they never do anything of worth. Beating the Eagles in the regular season is the most they ever aspire to. It’s funny because those roles used to be reversed when Irvin was a player. 

  • Jimmy Johnson

    INGLEWOOD, CALIFORNIA - OCTOBER 16: Former NFL head coach Jimmy Johnson looks on before the game between the Dallas Cowboys and the Los Angeles Chargers at SoFi Stadium on October 16, 2023 in Inglewood, California.

    (Photo by Harry How/Getty Images)

    Buddy Ryan definitely stoked the hate on this one. Jimmy and Buddy famously had several run-ins, including the infamous Bounty Bowl. But we also just hate him because he was the last successful coach for the Cowboys. He is the only Cowboy coach I put on here because none of the guys since didn’t coach well enough to be hated. I don’t hate Wade Phillips or Mike McCarthy, because they didn’t win. Say what you will about Jimmy, but he was a good coach and Jerry hasn’t been able to find a suitable replacement since him.

  • Jason Witten

    ARLINGTON, TX - OCTOBER 09: Jason Witten #82 of the Dallas Cowboys runs after catching a pass during the second quarter against the Cincinnati Bengals at AT&T Stadium on October 9, 2016 in Arlington, Texas.

    (Photo by Ronald Martinez/Getty Images)

    It was bad enough watching him play since he was a genuinely great TE. But he was more annoying after he left the Cowboys. Because then he became part of the worst Monday Night Football Crew ever. Between his fake hair, his lack of interesting analysis, and Booger McFarland’s dumb sideline setup blocking fans’ views, Monday Night Football became nearly unwatchable for that one season. Thankfully he is gone, and now we get Joe Buck and Troy Aikman (another guy who just missed making the list).

  • Greg Hardy

    ARLINGTON, TX - OCTOBER 11: Defensive end Greg Hardy #76 of the Dallas Cowboys on the sidelines before a game against the New England Patriots at AT&T Stadium on October 11, 2015 in Arlington, Texas.

    (Photo by Christian Petersen/Getty Images)

    This one is far more about him just being an awful person than it is about what he did with the Cowboys. Greg Hardy had one of the worst examples of Domestic Abuse we have seen from an NFL player. And yet even after all the information about what he did came out, including pictures of how badly he beat up his girlfriend, the Cowboys still signed him. Because Jerry Jones and the Cowboys have no morals, so why would they care if their players do?

  • Zeke Elliott

    SEATTLE, WA - AUGUST 25: Running back Ezekiel Elliott #21 of the Dallas Cowboys warms up prior to the preseason game against the Seattle Seahawks at CenturyLink Field on August 25, 2016 in Seattle, Washington.

    (Photo by Otto Greule Jr/Getty Images)

    Zeke was annoying before he became a Cowboy. So him getting drafted by the Cowboys (spending a high pick on an RB, another genius move by Jerry), just made sense. To his credit, he played very well against the Eagles in his time with the Cowboys. So that helped stoke the hatred.

  • Terrell Owens

    PHILADELPHIA - NOVEMBER 04: Terrell Owens #81 of the Dallas Cowboys reminds fans of the Philadelphia Eagles the score late in their game on November 4, 2007 at Lincoln Financial Field in Philadelphia, Pennsylvania.

    (Photo by Jim McIsaac/Getty Images)

    The traitor. TO went from beloved, to hated very quickly. He forced his way out of a great situation with what could have been a Super Bowl contender. To make it worse, he went to the enemy and stuck there for a long time. The guy could have been one of the most beloved Eagles of all time. Instead, he threw it all away because neither he, McNabb, or Joe Banner could put their massive egos aside, and a great team slowly fell apart.

  • Drew Pearson

    ARLINGTON, TX - APRIL 26: Former NFL wide receiver Drew Pearson speaks during the first round of the 2018 NFL Draft at AT&T Stadium on April 26, 2018 in Arlington, Texas.

    (Photo by Tom Pennington/Getty Images)

    I was not alive to watch Drew Pearson play, so I cant speak to what he was like as a player. But after watching his speech at the draft in Philly, it is easy to see I would have hated the guy when he played for the Cowboys. But it would be more like the hate we have for Deion, where there’s a level of respect, rather than the hate we have for Tony Romo. His speech, even if we hated it, was funny. And he is a Hall of Fame WR worthy of respect.

  • Jerry Jones

    INGLEWOOD, CALIFORNIA - OCTOBER 16: Dallas Cowboys owner and general manager Jerry Jones speaks on the ESPN set before the game between the Dallas Cowboys and the Los Angeles Chargers at SoFi Stadium on October 16, 2023 in Inglewood, California.

    (Photo by Kevork Djansezian/Getty Images)

    And the most hated Cowboy of them all. The guy who is the consistent presence across every era of the Cowboys. I almost like Jerry, just because his incompetence is to blame for the Cowboys being so irrelevant these past couple of decades. But then I remember what a weird creepy old man he is. The guy will seemingly do anything to win, which makes it all the more embarrassing for him he hasn’t done any winning these past 20+ years. Ever since they stopped letting him just buy every single player, his teams have been wildly mediocre.

  • The Cowboys Fans From Philly

    PHILADELPHIA, PENNSYLVANIA - OCTOBER 16: A Dallas Cowboys fan looks on during the game between the Dallas Cowboys and the Philadelphia Eagles at Lincoln Financial Field on October 16, 2022 in Philadelphia, Pennsylvania.

    (Photo by Mitchell Leff/Getty Images)

    These people aren’t part of the Cowboys, so they don’t count, but they are the real reason many of us still hate the Cowboys. They grew up here but decided to root for the team all of their friends and neighbors hate. They actively root for the misery of the people around them. I have no ill will toward Cowboys fans from the Dallas area. They are supposed to root for the Cowboys. But these people? They are the worst. They have never even been to Dallas but will wear their Dez Bryant jersey and get all chest even though they haven’t watching winning football in 26 years, and many have them have never seen it at all. These people will be endlessly playing We Dem Boyz on a loop but then cry themselves to sleep because they forget what it is like to have a relevant football team.

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