Ranking the Biggest Fail in the History of Each NFL Franchise

Adam LazarusSenior Analyst IMarch 3, 2011

Ranking the Biggest Fail in the History of Each NFL Franchise

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    Elsa/Getty Images

    Determining the biggest failures in the history of each NFL franchise is easy if you limit the shortcomings strictly to personnel moves.  Every franchise has the infamous Draft Day bust and the regrettable trade or free agent acquisition.

    But we’ve done both of those lists lately! Power Ranking the Most Disappointing Acquisition in the History of Each NFL Team and 2011 NFL Draft: Worst First-Round Pick in Every Team's History

    Instead, we’ve chosen each franchise’s biggest fail from other avenues. Whether it’s firing (or hiring) a coach, cutting a future superstar, or choking in a big game, these 32 moves were extremely embarrassing. 

Philadelphia Eagles: The 2002 NFC Championship Game

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    Al Bello/Getty Images

    When: January 19, 2003

    Perhaps it was fitting that the last Eagles game ever played at Veteran Stadium would leave the Philadelphia fans depressed.

    The Eagles were the NFC’s top seed in 2002, having posted a 12-4 record. They had the fourth highest scoring offense in the NFL and the second best scoring defense in the NFL.

    But that wasn’t the main reason why Donovan McNabb’s team was a huge favorite over visiting Tampa Bay in the 2002 NFC Title Game: the Bucs had never won a game (0-for12) in games played in temperatures 32 degrees or below. And the forecast for their showdown in Philly was 20.

    Still, after an explosive start—70-yard return on the opening kickoff, touchdown two plays later—the Eagles, not the Bucs, froze.

    The Eagles could only produce a field goal the rest of the way and allowed four scores by the mediocre Tampa offense. Ronde Barber sealed the crushing defeat by picked off a McNabb pass midway through the final quarter and returning it 92 yards for a game-clinching touchdown. 

New York Giants: The Miracle at the Meadowlands

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    When: November 19, 1978

    Perhaps the ultimate “fail” in NFL history.

    Against the moribund Giants, the visiting Eagles were buried: 31 seconds remaining, behind 17-12, no timeouts, opponent with the ball.

    Then the unthinkable happened. On third and two, rather than take a knee, Giants offensive coordinator Bob Gibson inexplicably called a handoff from Joe Pisarcik to Larry Csonka.

    The rest is history.

Washington Redskins: Hiring Steve Spurrier

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    A. Messerschmidt/Getty Images

    When: January 14, 2002

    Firing Marty Schottenheimer—who had just finished his first season with the Redskins on an 8-3 run—was bad enough.

    But to replace him with Steve Spurrier, a man with zero NFL coaching experience, was risky to say the least.

    That didn’t dissuade owner Daniel Snider from making the biggest blunder (among many) of his decade-long tenure in Washington.

    As bad as the overall record was—12-20—the poor offensive output from the legendary “Ol’ Ball Coach” was worse: they averaged 18 points per game, nearly half Spurrier’s mark in Gainesville.  

Dallas Cowboys: Jackie Smith’s Drop in Super Bowl XIII

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    When: January 21, 1979

    St. Louis Cardinals tight end Jackie Smith was a Hall of Famer. He went to five consecutive pro bowls, caught 490 passes for 7,918 yards and 40 touchdowns.

    And in his first and only season with the Dallas Cowboys—his last in the NFL—Smith caught a game-tying touchdown pass from Roger Staubach in the third quarter of a playoff win over Atlanta.

    But all most people remember him for was the pass he dropped three weeks later.

    Trailing the Pittsburgh Steelers by a touchdown late in the third quarter of Super Bowl XIII, Staubach spotted an open Smith in the back of the endzone. On third-and-three from Pittsburgh’s ten, Staubach fired a perfect pass to Smith, who promptly dropped the would-be touchdown.

    Dallas settled for a field goal instead of a touchdown and ultimately lost by that same four-point margin. 

     

Green Bay Packers: 4th and 26, 2003 NFC Divisional Game.

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    When: January 11, 2004

    You’re ahead 17-14 with 1:12 remaining in the fourth quarter. Your opponent, the Eagles, have no timeouts and they have the ball on their own 25-yard line. And it’s fourth-and-26. Gotta like those odds of advancing to the NFC Championship Game for the first time in five years.

    Nevertheless, the deep middle of the Packers Cover 2 didn’t get the job done. Eagles quarterback Donovan McNabb hit Freddie Mitchell right past midfield for a 28-yard gain. The Eagles promptly tied it with a field goal, then won the game in overtime.

    Not much more explanation needed: an epic fail. 

Chicago Bears: Heads, Not Tails

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    When: January 9, 1970

    Both the Steelers and Bears finished the 1969 regular season with horrific 1-13 records, so a coin toss was needed to determine who was to be given the first overall pick in the next year’s draft.

    Three weeks before draft day, Commissioner Rozelle asked Bears team president Ed McCaskey—George Halas' son-in-law—to call it in the air.

    But no one had taught him the old adage: Tails never fails.

    McCaskey called heads, the 1921 Silver Dollar landed tails, and Pittsburgh was awarded the top pick.

    The Steelers took Terry Bradshaw, the centerpiece of their four Super Bowl titles. The Bears dealt away the second-overall pick for Elijah Pitts (who was released in training camp), Lee Roy Caffey (who was traded away the following season), and Bob Hyland (who was dealt to the Giants the following season). 

Detroit Lions: Hiring Matt Millen

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    Tom Pidgeon/Getty Images

    When: January 10, 2001

    The Lions have never been to the Super Bowl. So hiring Matt Millen—a man who had won four Super Bowls during the 1980s—as team president and general manager made sense, from a distance. A very long distance.

    Millen had no administrative or coaching experience; he had only been a broadcaster.

    And it showed during his eight-year stay in Detroit.

    The Lions went 31-81, wasted a handful of top draft choices (Joey Harrington, Charles Rogers, Mike Williams, Roy Williams), endured an embarrassing string of on-the-field moments, like Marty Mornhinweg’s overtime decision and not long after Millen left, the worst single season (0-16) in NFL history. 

Minnesota Vikings: The 1998 NFC Championship Game

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    Jonathan Daniel/Getty Images

    When: January 17, 1999

    That Vikings team in 1998 was absolutely incredible. Everyone remembers Randy Moss, Cris Carter, and Randall Cunningham blowing up the scoreboard.

    Robert Smith also had an outstanding season, and on the other side of the ball was Hall of Famer John Randle and a pretty good defense.

    Now, people want to blame Gary Anderson for missing the field goal that would have clinched victory over the Falcons in the NFC Title Game—and they should since it was only a 38-yarder, on Astroturf, indoors—but that unstoppable offense was held to one score in the game’s final 35 minutes.

    That’s a tough pill to swallow since the Falcons were hammered pretty good two weeks later by Denver in Super Bowl XXXIII.

Atlanta Falcons: Hiring Bobby Petrino

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    Chris Graythen/Getty Images

    When: January 7, 2007

    Maybe the Falcons shouldn’t have fired Jim Mora. Regardless, they made the wrong choice for their next head coach.

    Forget the fact that he had only three years of NFL experience. There should have been “character issue” concerns about him: just six months earlier, he had signed a 10-year contract with Louisville, a contract that he honored about 1/20th of.

    Sure, Michael Vick’s sudden incarceration wasn’t “fair” to Petrino, but a head coach shouldn’t take a job for one player. He also shouldn’t resign in the middle of the season and do so by leaving a note in his player's locker.

    And he definitely shouldn’t take a new high profile head coaching job the next day. As bad as Nick Saban’s departure from the Dolphins was, Petrino’s was much worse. At least Saban lasted two full seasons. Petrino didn’t even coach one. 

New Orleans Saints: Hiring Mike Ditka

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    Elsa/Getty Images

    When: January 29, 1997

    Ditka’s overall record in the Crescent City was bad, but not atrocious: 15-33. In fact he won a far greater percentage of games than the other former Super Bowl winning head coach, Hank Stram, that the Saints hired long past his prime. 

    But his Chicago act didn’t work in New Orleans. The self-confidence and brashness that made Iron Mike fodder for Saturday Night Live prompted him to make moves like dealing the Saints entire 1999 draft for Ricky Williams.

    And since Jim Haslett immediately turned the team into a playoff contender the next year, that team had plenty of talent.

    Still, Ditka deserves endless credit for one thing: he is the only head coach in NFL history to keep not one, but two quarterbacks named Billy Joe.  

Tampa Bay Buccaneers: Letting Doug Williams Go to the USFL

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    When: August 9, 1983

    In addition to taking the Bucs—who had recently lost 26 straight games—to the 1979 NFC Championship Game, Doug Williams led Tampa Bay to two additional playoff berths in the next three seasons. In his final three seasons Williams was very good quarterback, averaging over 220 yards per game.

    And since Williams' demands weren’t terribly unreasonable—except to the stingy Hugh Culverhouse—letting him leave for a different LEAGUE and not just a different team, was a mistake.

    But because the Bucs spent basically the next quarter-century searching for another young franchise quarterback— Steve Young, Vinny Testaverde, Trent Dilfer, Craig Erickson, Shaun King, Chris Simms—the move had dire repercussions. 

Carolina Panthers: John Kasay’s Kickoff in Super Bowl XXXVIII

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    Andy Lyons/Getty Images

    When: February 1, 2004

    We tried not to put too much blame on kickers in some of these entries. For example, the biggest fail in Vikings history isn’t “Gary Anderson’s missed field goal” and, since it was a terribly difficult field goal (47 yards on grass), we didn’t choose Scott Norwood’s miss for the Bills entry.

    Panthers kicker John Kasay, however, doesn’t get a pass, not for a botched field goal, but for a botched kickoff.

    After tying the game in the final 1:08, the Panthers kicked off to the Patriots. Kasay couldn’t keep the ball in bounds and New England was given the ball at the 40-yard line.

    Maybe the Patriots would have scored the game-winning field goal anyway.

    Maybe Bethel Johnson would have returned the kickoff for a touchdown and Adam Vinatieri wouldn’t have even needed to attempt a game winning field goal.

    But maybe the Panthers would have tackled Johnson inside the 30, the Panthers would have stopped the Pats, and then won the game in overtime.

    Who knows?

    Still, in the final minute of a Super Bowl loss—the only one in team history—those questions will haunt a franchise. 

Seattle Seahawks: Hiring Jim Mora

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    Otto Greule Jr/Getty Images

    When: January 21, 2007

    Why hire a head coach—especially one who grew up, played his college ball, and started his coaching career in town—for one year?

    Mora wasn’t exactly Vince Lombardi, but he was young and had been fairly successful in Atlanta.

    Perhaps it was the right move: Pete Carroll seems to be off to a great start in Seattle.

    But it was still a blunder.

     

St. Louis Rams: Releasing Kurt Warner

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    Al Bello/Getty Images

    When: June 1, 2004

    Marc Bulger was a pretty good quarterback for a few seasons. He went to two pro bowls, led the Rams to a 12-4 record in 2003 and a playoff win.

    Hindsight is most definitely 20/20, but Bulger’s resume probably wasn’t enough to offset releasing the most popular player in the history of the St. Louis Rams.

    Now, the Rams didn’t make a mistake by cutting Warner because he was popular or because he HAD won them a Super Bowl.

    But considering Kurt Warner’s outstanding performance in Arizona from 2007-09, a period in which the Rams won a total of six games, it was a major miscalculation.

San Francisco 49ers: The Second Half of the 1957 Western Division Playoff

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    When: December 22, 1957

    We don’t know what long-lasting impact the mistakes made by the current regime in San Francisco will have.

    But there is no denying what happened to the 49ers after their 1957 playoff loss: they didn’t reach the postseason for another 13 years.

    Clearly suffering one of the worst collapses in NFL playoff history had a long lasting impact.

    Thanks to three touchdown passes by Y.A. Tittle, the host 49ers jumped out to a 27-7 second half lead over Detroit. Since the Lions were being quarterbacked by backup Tobin Rote, San Francisco certainly had the upper hand.

    Nevertheless, Rote led the Lions on a remarkable comeback, scoring 24 unanswered points to give his team a 31-27 victory and a berth in the NFL Title Game.

    The 49ers wouldn’t reach the league title game for nearly another quarter-century.  

Chicago/St. Louis/Arizona Cardinals: Firing Don Coryell

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    When: January 10, 1978

    Chicago/St. Louis/Arizona Cardinals: Firing Don Coryell

    From 1949 to 1981 the Cardinals franchise reached the playoffs only twice: in 1974 and 1975. The man at the helm of those two clubs was innovative head coach Don Coryell. He turned Jim Hart into a four-time Pro Bowler, won a pair of NFC East titles, and won over 60% of his games.

    But by the end of the 1977 season, a budding feud between Coryell and Cardinals management , especially owner Bill Bidwell—who actually changed the locks on Coryell’s office in early January 1977—prompted the team to fire their coach.

    It was a huge fail since Coryell immediately put together an incredible team in San Diego, taking the Chargers to consecutive AFC Championship Games.

    But since the Cardinals—who replaced Coryell with former Oklahoma Sooners legend Bud Wilkinson, a man 15 years removed from coaching—spent the next 30 years looking for a good replacement, it was an epic fail. 

New England Patriots: Super Bowl XLII

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    Jim McIsaac/Getty Images

    When: February 4, 2008

    Losing a Super Bowl really shouldn’t qualify as a historic fail. Unless it comes when the club is double-digit favorites, has arguably the greatest offense in NFL history, a defensive genius at head coach, and is one game away from a fabled “perfect season.”

    Of course the Pats fell to the underdog Giants, scoring just twice; a pretty paltry showing for a team that averaged 37 points per game and had scored 20 or more points in each of the previous 24 games.

    Everything seemed to go wrong for New England that day: the non-sack of Eli Manning, David Tyree’s helmet catch, allowing five sacks when they allowed just 21 all season.

    So even if the stars and the fates conspired to keep the 1972 Dolphins happy, the Pats' Super Bowl XLII  failure  was without a doubt the worst in franchise history.  

New York Jets: Richard Todd’s Performance in the 1982 AFC Championship Game

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    When: January 23, 1983

    Since Joe Namath and the Jets heroic moment in January 1969, the franchise has come to the doorstep of the Super Bowl four times.

    And although they lost each of those AFC Championship Games, the worst by far came in 1982.

    Certainly the 1982 Dolphins had a fine defense, the Killer B’s. And the nasty rain in South Florida made the Orange Bowl a quagmire.

    But that still can’t be enough to excuse Jets quarterback Richard Todd throwing five interceptions, only three less than he threw during the entire nine-game 1982 regular season.

    What would Todd’s college coach Bear Bryant—who died just three days later—have said?

Miami Dolphins: The 4th Quarter of “The Monday Night Miracle”

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    When: October 23, 2000

    The post-Dan Marino era was off to a great start in the fall of 2000. With Jay Fiedler under center, the Dolphins darted out to a 5-1 start.

    And in a huge Week Eight AFC East showdown on Monday Night in the Meadowlands, Fiedler and running back Lamar Smith gave the Dolphins a 30-7 lead heading into the final period.

    But—as Arnold Schwarzenegger told the ABC viewing audience—the Jets and Wayne Chrebet roared back.

    In that final period, Miami’s defense, which had allowed only 8.5 points per game coming into the game with the Jets, surrendered 23 points in the fourth quarter, forcing overtime.

    Naturally the Jets won in sudden death, completing one of the most horrible collapses in league history. 

Buffalo Bills: Starting Rob Johnson over Doug Flutie

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    Andy Lyons/Getty Images

    When: January 8, 2000

    As stated earlier in the Panthers entry, it’s not entirely fair to call Scott Norwood’s missed field goal a “fail.” It was a 47-yarder on grass that missed by inches and would have been the second longest field goal in Super Bowl history.

    Although a Super Bowl title wasn’t on the line, the Bills decision to start Rob Johnson over Doug Flutie in the last playoff game Buffalo played, was more catastrophic.

    According to many, it was owner Ralph Wilson’s mandate, not head coach Wade Phillips’ choice.

    No matter who made the call, it was the wrong one. Flutie had led the Bills to a 10-5 record and most recently a critical overtime road win over the Patriots. But for the meaningless Week 17 finale, Phillips started Johnson, who played (24-for-32, 287 yards, 2 TD) well against a Colts defense with nothing to play for.

    That convinced someone to start him the following week in their Wild Card game at Tennessee.

    Johnson completed less than half his passes for 131 yards as the Bills lost via the infamous Music City Miracle. 


Pittsburgh Steelers: Neil O’Donnell’s Second Interception, Super Bowl XXX

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    Mike Powell/Getty Images

    When: January 28, 1996

    Much like the Bills decision to start Rob Johnson over Doug Flutie, the truth behind this epic fail is a bit hazy.

    Many Steelers fans point to the insertion of rookie Corey Holliday into the lineup—to replace the injured Ernie Mills—as the reason why Neil O’Donnell threw the ball to “no one” and/or the Cowboys Larry Brown. Perhaps Holliday didn’t properly adjust his route, perhaps O’Donnell just made a horrible throw.

    Either way, it resulted in perhaps the most costly turnover in Super Bowl history.

    On the verge of a thrilling upset, and snapping the NFC’s 13-year winning streak in the Super Bowl, the Steelers, now down to the Cowboys 20-17 with four minutes remaining, had the ball at their own 32.

    But O’Donnell floated the pass to Brown, setting up the game-clinching touchdown and forever linking O’Donnell to Brown and Super Bowl blunders.

    It would be another 10 years until a Steelers quarterback had the opportunity to underwhelm in the Super Bowl. 

Baltimore Ravens: Letting Trent Dilfer Leave

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    Brian Bahr/Getty Images

    When: August 4, 2001

    Of course Trent Dilfer was, at best, an average quarterback. And even in the Super Bowl XXXV win over the Giants, he missed several open receivers, completing just 12 of 25 passes. (He also complete just 35 passes in four combined playoff games that postseason).

    Those stats were the main reason why the club chose Elvis Grbac over Dilfer the following summer.

    But Grbac—to whom they gave a far larger contract than what Dilfer had asked for—was a disaster, retiring after one year.

    And considering they were continually searching for and failing to find a new QB—Grbac, Anthony Wright, Kyle Boller, Jeff Blake, Chris Redman, Randall Cunningham—they largely wasted five years of Ray Lewis’ prime. 

Cleveland Browns: The Fumble

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    When: January 17, 1988

    The Browns history is filled with epic fails, and not just high draft choices, trades, or free agent signings.

    Everything from firing Paul Brown in 1963, Red Right 88, The Drive, LEAVING Cleveland(!), Orlando Brown’s ref-toss, the second half collapse in the 2002 Wild Card loss to Pittsburgh, Dwayne Rudd’s helmet toss, etc.

    But only one single fail actually kept the Browns from reaching a first-ever Super Bowl.

    After overcoming an 11-point second half deficit at Mile High Stadium, the Browns, behind 38-31, drove to the Broncos eight-yard line with 1:12 remaining in the game.

    Two yards from the end zone Browns back Earnest Byner was stripped by Jeremiah Castille, ending the Browns chances.

    As bad as "The Drive" was, that was a series of plays AND only forced overtime, where the Browns still had a chance. And Red Right 88 didn’t come with a Super Bowl berth on the line.

    “The Fumble” was the single most costly, heartbreaking moment in team history. 

Cincinnati Bengals: Lewis Billups Dropped Interception, Super Bowl XXIII

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    George Rose/Getty Images

    When: January 22, 1989

    Everyone remembers Joe Montana and the game-winning 92-yard drive which ended with John Taylor’s touchdown grab.

    But that play might never have happened had the Bengals been able to capitalize on perhaps the only bad throw Joe Montana made in a Super Bowl.

    Almost inexplicably, the Bengals had limited the great 49ers offense to just six points through the first three quarters of Super Bowl XXIII. But on the opening play of the final quarter, Montana hit Roger Craig on a critical 40 yard pass.

    On the next snap, Montana zeroed in on Taylor in the end zone, where Bengals corner Lewis Billups stepped in front of the ball. But he dropped the sure interception and on the very next play Montana hit Rice to tie the game at 13.

    Perhaps they would have won the game anyways, as the 49ers could have come back even with that turnover. But don’t ever give Jerry Rice and Joe Montana a second chance. 

Baltimore/Indianapolis Colts: Last Two Minutes, 2005 AFC Divisional Playoff

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    Jamie Squire/Getty Images

    When: January 15, 2006

    Plenty of number one seeds have lost their first (home) playoff game. So the Colts—who at one point in the 2005 season were 13-0—losing in the second round to Pittsburgh wasn’t the worst fail in team history.

    The way they lost that game on the other hand, is.

    After getting one of the greatest breaks in playoff history, Jerome Bettis’ goal line fumble with two minutes remaining—a remarkable comedy of errors ensued.

    Nick Harper—fresh off a sliced up knee courtesy of his wife the night before—was tripped up at midfield by Ben Roethlisberger. Then, after Peyton Manning drove the team into his range, Mike Vanderjagt, the so-called “most accurate kicker in NFL history,’ missed the game-tying field goal by a mile. 

Jacksonville Jaguars: 2nd Half of the 1999 AFC Championship Game

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    Andy Lyons/Getty Images

    When: January 23, 2000

    If you don’t count games against Tennessee, the 1999 Jacksonville Jaguars went undefeated. Of course, if you do count those three games, the 1999 Jags went winless.

    Losing the AFC Title Game alone isn’t enough to count as an epic fail: although when you’re at home and so close to reaching the first Super Bowl in five years, it’s pretty bad.

    No, it’s how they lost that third game to Tennessee that was pretty shameful.

    Fresh off an incredible 62-7 shellacking of the Dolphins in Round Two, the Jags hosted Tennessee, and jumped out to an early 14-7 lead.

    But after that, the NFL’s best defense (and the special teams) allowed 24 points while Mark Brunell and the AFC’s second-highest scoring offense was shut out.

    The Jags haven’t gotten that close to the Super Bowl since.

     

Houston Texans: Travis Johnson’s Taunt of Trent Green

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    When: October 7, 2007

    For a team that’s never reached the playoffs, there are probably bigger football-specific fails in the Texans short history.

    But Travis Johnson provided a pretty horrible moment in 2007.

    Sure Trent Green delivered a low blow (literally and figuratively) on Travis Johnson. But he saw Green motionless on the ground, and still taunted him. Fail.

     

Houston Oilers/Tennessee Titans: The Last 28 Minutes, 1992 AFC Wild Card Gam

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    Rick Stewart/Getty Images

    When: January 3, 1993

    Eddie George dropping a pass at midfield in the 2000 playoff loss to Baltimore was pretty bad, and cost the Titans a chance to return to the Super Bowl and avenge “The Tackle". But we can’t exclude the greatest collapse in NFL history.

    After taking a 28-3 lead into halftime on the road, the Oilers locked up their first playoff win over the two-time defending AFC Champions thanks to Bubba McDowell’s 58-yard interception return of a pass that went through Keith McKellar’s hands.

    Or so it seemed.

    With backup Frank Reich at the helm, the Bills scored five touchdowns in the next 12 minute stretch to take the lead.

    The Oilers didn’t completely fold, tying the game at the end of regulation. But the Oilers final miscue of the day, a Warren Moon interception, set the Bills up with an easy field goal attempt, completing the most embarrassing moment in Houston’s rich sports history. 

Kansas City Chiefs: Lin Elliott’s Performance in the 1995 AFC Divisional Playoff

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    Otto Greule Jr/Getty Images

    When: January 8, 1996

    Even after Joe Montana retired, the Chiefs didn’t skip a beat in 1995, posting a 13-3 record and gaining the AFC’s top seed in the postseason.

    And with the “ragamuffin” Wild Card Colts coming to town, they seemed destined for (at least) a trip to the AFC Championship Game.

    Four turnovers greatly did in the Chiefs that night in Arrowhead. But had Lin Elliott not missed a 35-, 39-, and a 42-yard field goal, the Chiefs probably wouldn’t have lost by a 10-7 final score.

    Again, one missed field goal—even from a reasonable distance—doesn’t qualify as an epic fail. But how about three? 

San Diego Chargers: Marlon McCree's Fumble

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    Jonathan Ferrey/Getty Images

    When: January 14, 2007

    The Chargers had their best season in team history in 2006, going 14-2 and earning the top seed in the playoffs. With MVP LaDainian Tomlinson, budding passer Phillip Rivers, and the NFL's seventh ranked defense. 

    In their first playoff game the mighty Patriots came to Qualcomm Stadium, and with the game tied at 13 midway though  the final quarter, Tomlinson's one-yard touchdown took the lead.

    Then, safety Marlon McCree picked off Tom Brady on a fourth down and--since they had the NFL's leading rusher--it seemed they would be capable of running out the clock on New England.

    But while running with the ball McCree was stripped  by the Pats Troy Brown, Reche Caldwell recovered the fumble and four plays later New England tied the game. 

    The Chargers fine defense continued to collapse as Brady drove the Pats down the field for the game winning field goal in the final minutes. 

    San Diego never had a more perfect road to the Super Bowl and they ended up being one-and-done. 

Oakland/Los Angeles Raiders: Trading Jon Gruden

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    Brian Bahr/Getty Images

    When: February 18, 2002

    Gruden and owner Al Davis were never going to co-exist. And since Davis seems incapable of co-existing with any coach, it’s tough to heap the blame on Gruden.

    Still, the decision to trade Gruden to Tampa Bay couldn’t been any more disastrous than it was.

    Forget the fact that when the Raiders reached Super Bowl XXXVII, they had to play the Buccaneers and Gruden, the one man who knew them better than they knew themselves.

    But the two first and two second round draft picks they got in return for Gruden (Tyler Brayton, Langston Walker, Teyo Johnson) produced almost nothing. 

Denver Broncos: Hiring Josh McDaniels

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    Doug Pensinger/Getty Images

    When: January 12, 2009

    Again, for a hiring to land on this list, it has to be about more than just won-loss records: Ditka dealt away the Saints entire draft in addition to a terrible record, Steve Spurrier was all hype, no results, Bobby Petrino bailed on the team after just 14 weeks, etc.

    And the same is true for Josh McDaniels.

    Even if he was extremely young and there was a Yoda-like “he is not ready” vibe coming from Bill Belichick, the move made sense. He was capable, turning the sans-Tom Brady Patriots into the fifth best offense in the NFL, and he had spent nearly a decade with an NFL dynasty.

    Still, even the best laid plans sometimes fall apart. In addition to losing 12 of his last 17 games, he dealt away Brandon Marshall for less than he was worth (two second-rounders) after doing the same with Jay Cutler.

    And if the Tim Tebow selection does turn out to be a bust, McDaniels’ legacy of mistakes will be saddled with that as well.