Aug 5, 2026 12:00 PM

Cowboys Whitt's End: From the glory of the Triplets to decades of quarterback carousels, a veteran insider traces 30 years of heartbreak, roster gambles, and Jerry Jones’s elusive championship pursuit.

DALLAS - Eight head coaches. 26 starting quarterbacks. 2 stadiums. 30 dashed Super Bowl dreams.

One general manager.

I know Jerry Jones is the obvious common denominator in the Dallas Cowboys’ record drought. But there’s plenty of blame to go ‘round.

The Cowboys won Super Bowl XXX in the 1995 season. Since then they’ve held 30 training camps boasting supposed catalysts, hyped heroes and, ultimately, irrational championship hopes.

Though this week in Oxnard Jones said “it’s not a far reach” to think his team can reach Super Bowl LXI in February, expectations are undeniably muted. There’s no contract drama. No significant injuries. But, also - given 250-1 longshot odds - no unbridled optimism.

In the past, mantras like “Glory Hole!” and “All In!” wound up on Cowboys’ training camp T-shirts. Doubtful that fans will clamor for “Not a Far Reach!” bumper stickers this summer.

This year’s hope is founded on the belief that the NFL’s second-best offense will be supplemented by new coordinator Christian Parker and two first-round defensive picks in Caleb Downs and Malachi Lawrence.

Alas, we’ve been sold a version of this story before. In my 30 For 30, a look at the Cowboys’ season-by-season dreams of a Super Bowl … and the ultimate disappointment.

1996

Dream: Troy Aikman, Emmitt Smith, Michael Irvin, Deion Sanders in their elite prime.

Disappointment: NFL Suspensions to Irvin, Erik Williams and Leon Lett harpoon the dynasty.

1997

Dream: Aikman, Emmitt, Irvin, Deion in their prime. Still.

Disappointment: Tension and conflict between Aikman and head coach Barry Switzer tear apart the locker room.

1998

Dream: New head coach Chan Gailey brings offensive creativity, discipline.

Disappointment: Drafting Greg Ellis over Randy Moss.

1999

Dream: One last gasp from the Canton-bound Triplets.

Disappointment: Irvin, fullback Daryl Johnston suffer career-ending injuries.

2000

Dream: Trade for receiver Joey Galloway gives Aikman a fresh, deep threat.

Disappointment: Galloway tears ACL in opener; Aikman suffers career-ending concussion.

2001

Dream: Free-agent quarterback Tony Banks brings increased athleticism, energy.

Disappointment: Banks is cut during training camp, replaced by rookie Quincy Carter.

2002

Dream: Emmitt sets NFL rushing record in season featured on HBO’s Hard Knocks

Disappointment: Head coach Dave Campo botches multiple in-game decisions, leading to his firing after three consecutive 5-11 seasons.

2003

Dream: Legendary new head coach Bill Parcells infuses championship DNA.

Disappointment: Quincy starts all 16 games at quarterback, including lopsided Wild Card loss.

2004

Dream: Under Parcells’ stern tutelage, Quincy blossoms into elite quarterback

Disappointment: Failing yet another drug test, Quincy is released during training camp and replaced by 41-year-old Vinny Testaverde.

2005

Dream: Parcells steadies ship by bringing in another of his former quarterbacks, veteran Drew Bledsoe.

Disappointment: Darren Woodson retires; Bledsoe just another re-tread.

2006

Dream: Controversial signing of receiver Terrell Owens proves Jerry’s urgency to win now.

Disappointment: Undrafted Tony Romo emerges as quarterback, but fails in playoff loss as a holder. After only referring to T.O. as “the receiver” during the season, Parcells quits.

2007

Dream: Laid-back, defensive-minded new head coach Wade Phillips brings welcome attitude adjustment to talented roster.

Disappointment: Despite a 12-1 start and home-field advantage in NFC Playoffs, upset loss to Giants stunningly ends promising season.

2008

Dream: Talented-but-troubled cornerback/kick returner Pacman Jones signed as missing piece.

Disappointment: After getting suspended for a fight at a Dallas hotel, Pacman plays only nine ineffective games.

2009

Dream: Releases of Pacman, safety Roy Williams and quarterback Brad Johnson signal commitment to youth, discipline.

Disappointment: One of the worst drafts in franchise history as none of their 12 picks ever makes a significant contribution.

2010

Dream: Coming off a playoff win, Romo has talent to lead team to Super Bowl XLV at Cowboys Stadium.

Disappointment: Romo suffers a season-ending injury in Week 6, replaced by Jon Kitna and Stephen McGee.

2011

Dream: Former Aikman backup and innovative offensive mind Jason Garrett will kick-start Romo as new head coach.

Disappointment: Despite a healthy Romo, four losses in last five including a blowout in a de facto NFC East Championship Game Week 17 in New York.

2012

Dream: Colorful new coordinator Rob Ryan, No. 6 overall draft choice Morris Claiborne and free-agent safety Brandon Carr will drastically improve defense.

Disappointment: Claiborne underwhelms with only one interception in 15 starts in another seasons that ends in a pivotal Week 17 loss.

2013

Dream: Romo, rapidly rising receiver Dez Bryant and running back DeMarco Murray provide elite offense.

Disappointment: Romo suffers back injury in Week 16 win, leaving backup Kyle Orton to start - and lose - do-or-die season finale to Eagles.

2014

Dream: Center Zack Martin - drafted over Johnny Manziel - adds seventh Pro Bowl starter to championship-caliber offense.

Disappointment: Dez caught it. But it was ruled he didn’t.

2015

Dream: New contracts to Garrett and defensive coordinator Rod Marinelli ensures stability at the top.

Disappointment: Injuries to Dez (Week 1) and Romo (Week 2) essentially end a season in which defense records only eight interceptions.

2016

Dream: No. 4 overall pick Ezekiel Elliott and 4th-rounder Dak Prescott provide youthful infusion for oft-injured Romo.

Disappointment: Promising rookie revolution ruined by Packers’ 51-yard field goal on final play of heartbreaking home playoff loss.

2017

Dream: With Romo retired, path is cleared for Prescott to ascend into superstar face of America’s Team.

Disappointment: Dak regresses and No. 1 draft pick Taco Charlton is an immediate bust.

2018

Dream: Departure of Dez mitigated by trades for offensive weapons Tavon Austin, Amari Cooper.

Disappointment: After a home playoff win, defense surrenders three touchdowns and 273 yards on the ground at Rams.

2019

Dream: Trade for Robert Quinn and drafting of Trysten Hill will upgrade porous defense.

Disappointment: Defense improves only marginally as Garrett and Marinelli are let go after season.

2020

Dream: New head coach Mike McCarthy will develop Dak like he did Brett Favre and Aaron Rodgers in Green Bay.

Disappointment: Dak suffers a season-ending injury in Week 5 and is replaced by Andy Dalton, Garrett Gilbert and Ben DiNucci. New coordinator Mike Nolan’s defense coughs up a franchise-record 29.6 points per game.

2021

Dream: In a camp chronicled on Hard Knocks, Dak is armed with a new $160 million contract and the defense invigorated by the drafting of rookie Micah Parsons.

Disappointment: Clock mismanagement and sloppy officiating costs Dallas one last snap in the Red Zone in an excruciating home playoff loss to 49ers.

2022

Dream: Acquisitions of Dante Fowler and Anthony Barr provide defensive playmakers to complement Dak’s offense.

Disappointment: Dak fails to deliver in another post-season loss to San Francisco.

2023

Dream: Veteran receiver Brandin Cooks brings deep threat to offense lacking speed.

Disappointment: Despite record-setting offense in third consecutive 12-5 season, Dak again flops in embarrassing home playoff loss to Packers

2024

Dream: Fueled by playoff pratfalls and a second-place finish in MVP voting, now 30-year-old Dak is supremely motivated to prove his worth.

Disappointment: Dak suffers season-ending hamstring injury in Week 9, replaced by Cooper Rush and Trey Lance.

2025

Dream: New head coach Brian Schottenheimer transforms vibe and culture with refreshing enthusiasm and gimmicky motivational ploys.

Disappointment: Micah is traded to Packers and coordinator Matt Eberflus oversees the worst defense in franchise history.

2026

Dream: Training camp opens with no contractual drama and no injuries, with new coordinator Christian Parker promising to revamp ailing defense.

Disappointment: TBD ...

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