In close to six decades in the NFL, the Dallas Cowboys have been one of the league's most successful, in terms of their five Super Bowl wins, the many Hall of Fame players who passed through their ranks, and their 20 straight winning seasons from 1966 to 1985. Up to this day, we remember people like Tom Landry, his fedora, and his 29 seasons as head coach, that Hail Mary pass-innovating Roger Staubach, '90s heroes Troy Aikman, Emmitt Smith, and Michael Irvin, and more recently, tight end extraordinaire Jason Witten, and we look forward to guys like Ezekiel Elliott and Dak Prescott taking their place alongside said greats.
Then we also remember the shameful and lowly moments that have come with the good times for "America's Team." We remember the decadent shenanigans of Irvin, Nate Newton, Charles Haley, and others during the '90s Super Bowl era, and cringe as we recall how Barry Switzer and Dave Campo aren't exactly Landry, Jimmy Johnson, or Bill Parcells. We think of the legal problems of the aforementioned '90s Cowboys, Randy Gregory, and Greg Hardy. And we think of every time Tony Romo disappeared or made boneheaded plays when he should have been playing like he did for most of the season.
The 'Boys may have achieved greatness several times over in the NFL, but they aren't perfect either. Here are 20 moments that rank as the most embarrassing, disappointing, or just plain lowest in the team's history.
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20 Romo Disappears In Win-And-In Games (Take Your Pick)
Tony Romo deserves a lot of credit for enjoying tremendous NFL success as an undrafted Division I-AA quarterback, but he's also been criticized heavily for his inability to deliver when it matters the most. That includes quite a few moments when the Cowboys were in a “win-and-in” situation — one win, and you’re in the playoffs.
Probably the most infamous example of such came in Week 17 of the 2008 season when the Philadelphia Eagles hosted the Cowboys in a game. Sure, it was a road game, but that didn’t excuse Romo for throwing one pick-six and no touchdown passes and underperforming (with the rest of the team) as Dallas got walloped, 44-6.
19 Tashard Choice Asks For Michael Vick’s Autograph
Players have been sanctioned for laughing after a loss or, if you want the exact opposite, for making a scene by lashing out at a teammate or coach after a loss. But running back Tashard Choice was different, as he went up to Eagles quarterback Michael Vick after the Cowboys lost to Philadelphia in a December 2010 game. He didn’t get physical, and he didn’t even talk trash — he asked the guy for his autograph!
It’s fair enough — Choice wanted to show his respect to the winning quarterback, he’d known Vick for a while, and the autograph was for his nephew. But it was weird and awkward nonetheless for most — the Eagles, as you should know, are the Cowboys’ divisional rivals!
18 Randy Gregory’s Waste Of Potential
A second-round pick who nonetheless came with first-round talent, Randy Gregory dropped down in the 2015 draft after failing a test during the combine. During his rookie season, Gregory battled injuries which stifled his productivity quite a bit but didn’t disguise the fact that he was still showing a lot of promise. Then came the 2016 season, when he failed multiple tests and played just two games, and the 2017 season, where he didn’t play a single down, again due to suspension.
Gregory was finally reinstated into the NFL earlier this month, and while he’s still young enough to live up to his tremendous potential, it’s going to be quite hard to trust him to stay clean going forward.
17 Drafting Dwayne Goodrich
Already, it was seen as a reach for the Cowboys to select cornerback Dwayne Goodrich in the second round of the 2000 draft, with hopes that he’d fill the void to be left by Deion Sanders. It wasn’t like there were Hall of Fame-caliber corners hidden at that point in the draft, but Goodrich definitely didn’t produce like a second-rounder is expected to.
The bottom fell out for Goodrich in January 2003, when he was involved in an off-field issue that ended up with him being incarcerated. It was a waste of talent and a draft pick for Dallas.
16 The 1989 Season
Things had the potential to get much better for the sadsack Dallas Cowboys of the post-Tom Landry era, but before they did, they had to get a little worse. The Cowboys had not just one, but two potential quarterbacks of the future in Troy Aikman and Steve Walsh. Young guys like Michael Irvin, Daryl Johnston, Nate Newton, and Ken Norton Jr. were already in place as future Super Bowl mainstays.
However, that was just it – this was a very young team with two rookie QBs, and they played like one from the very first regular season game, where they got routed by the Saints, 28-0. The 1989 Cowboys finished with a pathetic 1-15 record, bad enough for second worst in team history.
15 Ezekiel Elliott's Issues
When Ezekiel Elliott made a huge impact in his rookie season in 2016, Cowboys fans immediately thought they had someone who could one day rival Emmitt Smith as the team's greatest running back ever. Unfortunately, there was a huge cloud hovering over his head all throughout that season.
While he was supposed to be suspended for the first six games of the 2017 season, Elliott appealed the decision, which led to a frantic back-and-forth of sorts – will he, or won't he have to sit out? Ultimately, it was decided that he would, though Elliott came pretty darn close to a thousand rushing yards despite missing all those games in his second pro season.
14 The Winless Debut Campaign
Very few sports expansion teams will ever go as far as the Vegas Golden Knights did in their first NHL season. Even the NFL's own Panthers and Jaguars had losing debut seasons, one year before they both made surprising playoff runs. The Dallas Cowboys, on the other hand, were more like your typical expansion team.
In 1960, the Cowboys were winless, going 0-11-1 in what was then, and up to now, one of the worst win-loss records in NFL history. They had no stars whatsoever (Don Meredith was still a rookie, and a backup), and their coach was an innovative, yet young and inexperienced guy named Tom Landry. Good thing the Cowboys held on to him despite those early struggles.
13 Not Immediately Replacing Troy Aikman As Franchise QB
The New England Patriots had better take note, because they wouldn’t want to be like the Cowboys from 2001 to 2005, in between Troy Aikman and Tony Romo. For five futile years, the Cowboys toggled between mediocre youngsters (Quincy Carter, Chad Hutchinson), certified draft busts (Ryan Leaf), nondescript journeymen (Anthony Wright), and past-their-prime veterans (Vinny Testaverde, Drew Bledsoe) as they went 35-45 in this comparatively “dark age,” 40-56 if you count Aikman’s final season behind center.
Fortunately for big D, Tony Romo proved to be an undrafted gem when he replaced Bledsoe midway through the 2006 season, though his poor clutch performance, as evident in this list, has been well-documented.
12 The Joey Galloway Debacle
There are bad signings and trades in Cowboys history, and there’s the Joey Galloway deal. Galloway had a productive run with the Seattle Seahawks, and the Cowboys thought he was worth first-round picks in the 2000 and 2001 drafts. Heck, they needed someone to replace Michael Irvin, and Galloway looked like the perfect choice.
Unfortunately, Galloway was dead weight in his first season as a Cowboy after he tore his left ACL, and when he returned a year later, he was as average as you could get. He was definitely not worth the two first-round picks the Cowboys gave up for him, and he was arguably the player fans remember when they think about the much-lamented Dave Campo era in Dallas.
11 Emmitt Smith's Holdout
When you've got one of the NFL's best running backs, you want to pay him every cent of what he deserves, even if it means breaking the proverbial bank. But that's not how it was for Jerry Jones in the 1993 offseason, as he thought he could lowball Emmitt Smith and give him an unsatisfactory deal, with the expectation he'd still want to play, no questions asked, for the defending Super Bowl champion.
As it turned out, Smith was offended enough by the offer to hold out for the first two games of the 1993 season, which Dallas lost. That finally forced Jones to open up his wallet and re-sign Smith to a lucrative (for the era) four-year, $13 million deal.
10 Draft Busts David LaFleur And Bobby Carpenter (Tie)
Throughout the years, the Dallas Cowboys have had a very good drafting record, as so many high draft picks have lived up to the hype, while several later-round picks like Roger Staubach and Jason Witten proved to be absolute steals. However, the Cowboys have also chosen their share of absolute stinkers in the first round.
Most teams would have seen LaFleur’s weight (272 pounds for a tight end) as a red flag, but that didn’t stop the Cowboys from choosing him 22nd overall in 1997 and getting four mediocre-to-bad seasons from the former LSU star. Carpenter, a linebacker picked 18th in 2006, was given the unflattering nickname “Barbie” for his soft, uninspiring play over four similarly disappointing Cowboys seasons.
9 The Barry Switzer Regime
When the friction between Jerry Jones and Jimmy Johnson led to the latter's departure as head coach, everyone knew the Cowboys, and Jones had made a mistake. Johnson was a stern disciplinarian, but he was probably the only man who could keep the hard-partying, Super Bowl-winning Cowboys in line. In his place stepped Barry Switzer, who was the exact opposite.
With nice guy Switzer in charge, Dallas still won one Super Bowl, but it was increasingly a case of the inmates (Michael Irvin, Charles Haley, et al.) running the asylum in Big D. Switzer resigned after an underachieving 6-10 season in 1997 and a much-publicized incident where he was arrested for carrying a gun into an airport and fined a whopping $75,000 by the Cowboys.
8 The Quincy Carter Experiment
Despite a subpar junior season at Georgia, the Dallas Cowboys thought they had their quarterback of the future when they selected Quincy Carter 53rd overall in the 2001 draft. While the Cowboys made Carter their Week 1 starter in 2001, he was soon splitting starts with a motley crew of busts and nobodies that included Ryan Leaf, Anthony Wright, and Clint Stoerner.
To the surprise of many, Carter started all 16 games for the Cowboys in 2003 as new head coach Bill Parcells led the team to a 10-6 record. Unfortunately, he was a surprise cut in August 2004 over a failed drug test, as the legal problems (and CFL/minor league stints) mounted up in the years that followed.
7 Tom Landry Gets Fired
As the dust cleared in the aftermath of the Cowboys' disastrous 3-13 campaign in 1988, Jerry Jones purchased the team and immediately tried to flex his muscle, making the most controversial decision any new owner could make – he fired the great Tom Landry after 29 seasons as head coach.
Granted, Landry was to turn 65-years-old in the 1989 season, and changes had to be made as the Cowboys seemed to get progressively worse during their mid-late '80s swoon. But Jones' reckless move immediately turned off legions of faithful Cowboys fans, who were justifiably upset at the firing of an institution. He has to be very thankful everything eventually turned out fine after Jimmy Johnson's arrival.
6 Dallas Lets Emmitt Smith Sign With Cards
When a player’s era is about to end, you want it to end with the same team he’s played for since the start of his career, if applicable. Magic Johnson spent his entire NBA career as a Laker, and unless some cataclysmic rift develops between Tom Brady and Bill Belichick, ol’ No. 12 will certainly be a New England Patriot from start to finish. The Dallas Cowboys, on the other hand, let Emmitt Smith spend the final years of his NFL career with the Arizona Cardinals.
To be fair, Smith was allowed to walk at a point when he was past his prime, but the least Dallas could have done was let him stick around as a backup running back after he was done breaking Walter Payton's career rushing yardage record.
5 Jackie Smith Drops Game-Tying TD At Super Bowl XIII
It may not have been a do-or-die situation for the Cowboys, but it was nonetheless a missed opportunity at Super Bowl XIII, one that could have helped them to a come-from-behind win. With the Terry Bradshaw-led Pittsburgh Steelers ahead 21-14, Roger Staubach spotted a wide-open Jackie Smith and threw the ball to him on third-and-3. Sounds like a sure score, doesn’t it?
While Smith was at the tail-end of a Hall of Fame career at tight end, there was no excusing how he completely botched the play, as the ball bounced off his chest and the pass ended up incomplete. The final score? Steelers 35, Cowboys 31.
4 Dave Campo As Head Coach
Despite all the flak that Barry Switzer and Jason Garrett get from Dallas Cowboys fans, at least they were able to compile winning seasons and lead the team to the playoffs, with Switzer even winning a Super Bowl, as previously stated. At least they didn't end up like Dave Campo, who compiled a 15-33 record in three losing seasons in Dallas.
Up to this day, Campo is still the only Cowboys coach never to lead the team to a winning record or playoff season. However, let's try to be fair to the guy – he took over the Cowboys in 2000, at a time when the team had just lost Michael Irvin, with most of the lineup, including Troy Aikman and Emmitt Smith, either aging and/or ineffective.
3 Leon Let(t)s The Dolphins Steal The Thanksgiving Classic
Leon Lett was a talented part of the Cowboys’ defense in the 1990s, making two Pro Bowls and winning three Super Bowls as a defensive tackle. He’s also been responsible for some truly head-scratching moments in Cowboys history, including his gaffe at the 1993 Thanksgiving Day game between Dallas and Miami.
With the Cowboys up 14-13 with 15 seconds to go, the Dolphins attempted a field goal, which ended up blocked and seemingly guaranteed a win for Dallas. Unaware that the game was effectively over, Lett tried to recover the ball but slipped in embarrassing fashion, allowing Miami to regain possession and retry the field goal, this time making good on it. Now that's what you call snatching defeat from the jaws of victory.
2 Romo's Botched Snap
It's already been established in this list that Tony Romo was a great numbers guy who led America's Team to some good seasons, but as far as you can get from a great clutch performer. No crunch time failure has stood out more than the time he botched a snap in the 2006 wild-card game against the Seattle Seahawks.
It was something so simple, something so routine – Romo merely had to hold the ball and set it up for Martin Gramatica and a potentially easy game-winning field goal. Sadly, Romo fumbled the hold and tried making up by running to the end zone, but got tackled just one yard short of a touchdown. You had one job, Tony. One job.
1 Greg Hardy's Lone Season In The Lone Star State
Greg Hardy was a monster when he played for the Carolina Panthers, as he emerged as one of the NFL's top defensive ends and a seemingly perennial sack leader. Unfortunately, it was during the peak of his career when reports alleged that Hardy was, away from the field, a misguided human being. Off-field issues landed him in trouble with NFL officials, but the Dallas Cowboys still thought he'd be worth the red flags he came with.
Unfortunately, he wasn't. The Hardy who played for the Cowboys wasn't just a shadow of his old self, but also a poor locker room influence to the younger guys on the team. He's since left professional football and kicked off a career as a professional mixed martial artist.
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