From those early days as the NFL’s first modern-day expansion team, to the championship years of the 1970s under coaching genius Tom Landry, to the 1990s dynasty led by the two JJs — owner/general manager Jerry Jones and head coach Jimmy Johnson, to the present day with Dak Prescott and Ezekiel Elliott as the stars of the present and the future. The Dallas Cowboys have had quite an interesting history in close to six decades in the NFL, and they’ve long carved out a reputation as one of the few teams whose logo, culture, and oftentimes players are familiar even to casual fans. In short, they’re “America’s Team,” and a pretty successful one for the most part.
It is indeed true that the Cowboys have had two dominating decades in the NFL, and have made some great personnel moves, through the draft, free agency, and in terms of the coaches they hired. But they’ve also drafted some head-scratching busts, signed some overpaid stiffs or locker room cancers, and hired some coaches who couldn’t quite lead and/or innovate like Landry and Johnson had.
When did the Dallas Cowboys add the right people at the right time, and when did they waste money on players or coaches who ultimately weren’t up to snuff? We’ve got them all listed here — eight of the Cowboys’ best, and seven of their worst personnel moves of all time.
15. BEST: DRAFTING EZEKIEL ELLIOTT AND DAK PRESCOTT (2016)
The reason this ranks so low is because it only happened last year, and Cowboys rookies Ezekel Elliott and Dak Prescott have years of NFL football to look forward to. But it was a brilliant move to draft these two dynamic youngsters in 2016, with Elliott being a no-brainer at fourth overall. Although plagued with legal problems stemming from an alleged domestic dispute, Elliott proved to be worth the hype as one of the best running backs to enter the NFL in quite some time. He finished the 2016 season with 1,631 yards and 15 touchdowns rushing, and looks to be on track to join Tony Dorsett and Emmitt Smith, among others, as an all-time great Cowboys RB in the making.
In an ordinary season, Zeke would have made a good choice for Offensive Rookie of the Year. But that was because the award went to Dak Prescott, a comparatively unheralded quarterback picked in the fourth round in 2016. Originally slated to be a third-stringer, this prospective understudy to Tony Romo turned Romo into a Wally Pipp-ian figure. Prescott led the Cowboys to an 11-game winning streak, as Dallas chose to go with him even when the aging Romo returned from injury. Sophomore jinxes notwithstanding, the Cowboys look to have found their next superstar QB in Prescott.
14. WORST: SIGNING GREG HARDY (2015)
This was a bad deal, but it’s not the worst. And the very reason is that the Cowboys only signed defensive end Greg Hardy to a one-year contract in 2015. But the fact that they signed Hardy was enough to cause uproar among fans, and it’s easy to see why. In the 2014 offseason, he was found guilty of assaulting his ex-girlfriend, and the Carolina Panthers reacted by deactivating him for all but one game in the season. While he was definitely a talented pass rusher, he was also a disruptive personality with multiple red flags. And many of those red flags were flying as the Cowboys dropped from 12-4 in 2014 to 4-12 in 2015.
What red flags were those? Well, there were the “inappropriate” tweets, numerous cases of tardiness, and allegations that he was a bad influence to younger players like Randy Gregory. The Cowboys cut him after that one tumultuous and inconsistent season, and it’s safe to say he isn’t missed by anyone in the locker room.
13. BEST: SIGNING DEION SANDERS (1995)
A two-sport star in baseball and pro football, “Neon” Deion Sanders was one of the fastest and most exciting defensive players of his time, a top-flight cornerback who starred for the Atlanta Falcons from 1989 to 1993, then for the Super Bowl-winning San Francisco 49ers in 1994. That season, he returned a whopping three interceptions for touchdowns and won Defensive Player of the Year honor. But for the 1995 season, he was a free agent, and NFL teams were eagerly taking part in the so-called “Deion Sweepstakes.”
Love him or hate him, Jerry Jones made some great moves as he transformed the Cowboys from afterthoughts to contenders, and one of them was signing Sanders to a free agent contract 1995. Despite the fact that Oakland offered him bigger money, he was still the highest-paid defensive player in the pros as a Cowboy, and he was worth every cent of his seven-year, $35 million deal. Just as he hoped, he won a second straight Super Bowl as a player at Super Bowl XXX, and made four Pro Bowl appearances before his 2000 release due to salary cap reasons.
12. WORST: THOSE MID-‘90s DRAFT CLASSES (1994-95, 1997)
It would seem as if the Dallas Cowboys suddenly forgot how to make good draft picks in the mid-‘90s, just as they were winning Super Bowls or at least contending for them. In 1994, they selected DE Shante Carver, a player who routinely shows up when people list the worst Cowboys draft picks of all time. The next two years, they didn’t have any first-rounders. In 1995, Sherman Williams and Kendell Watkins didn’t make much of a splash, even as backups, and offensive lineman Shane Hannah got injured before eating his way out of pro football, never getting to play in the NFL. And how can you forget tight end David LaFleur, the 1997 first-rounder whose performance, unlike his surname, stunk to the high heavens?
On a positive note, the 1996 draft class wasn’t too shabby, as second-rounders Kavika Pittman and Randall Godfrey became solid starters, and Dexter Coakley played even better as a 1997 third-rounder. And 1994 second-rounder Larry Allen is a Hall of Famer at offensive guard. Still, this was an era that produced two epic first-round failures, and a good percentage of second- and third-rounders with limited impact.
11. BEST: DRAFTING WELL IN THE EARLY YEARS (1961, 1963-66)
The Dallas Cowboys took just six seasons to crack the .500 mark, and the year after, in the 1966 season, they had their first of 20 straight winning seasons, which is still an NFL record. Seven seasons from winless expansion team to championship contender is quite the feat to pull off, and the Cowboys did it largely through their productive rookie drafts.
Bob Lilly (1961), Lee Roy Jordan (1963), Mel Renfro, Bob Hayes, and Roger Staubach (1964), Craig Morton and Jethro Pugh (1965), and John Niland and Walt Garrison (1966) were all key players as the Cowboys rose from the bottom to the top in very quick fashion. Most of them have gone on to the Pro Football Hall of Fame or may be in consideration for future inductions. Sure, there were some bad picks, such as 6’7” quarterback Sonny Gibbs (second round, 1962) and defensive lineman Scott Appleton (first round, 1964), but the Cowboys had an great track record in those early drafts.
10. WORST: DRAFTING STEVE WALSH (1989)
It was a selection that didn’t make any sense for anyone not named Jimmy Johnson. With the Dallas Cowboys having picked UCLA quarterback Troy Aikman first-overall in 1989, America’s Team appeared set for the future, and ready to rebuild. But Jerry Jones fired Tom Landry soon after, replacing him with Johnson, who wanted to pick his own star quarterback at the University of Miami, Steve Walsh, first-overall, in the supplemental draft. That meant the Cowboys would have two promising rookies competing for the starting QB role, and would have to surrender their 1990 first-rounder.
It was evident that Johnson had more faith in the last QB he coached in college, but it didn’t make much sense, as Dallas already had a potential future stud in Aikman. But with both rookies competing for minutes, they struggled accordingly, and the Cowboys stumbled to a 1-15 record. Just think what could have happened had the Cowboys still gotten to pick first-overall in 1990 —they could have addressed their linebacker woes with Junior Seau, while still getting to draft Emmitt Smith at 17th overall. Instead, they got Walsh, who had a fairly long, yet mediocre NFL career, and was gone from Dallas early in his second season.
9. BEST: TRADING STEVE WALSH (1990)
If drafting Steve Walsh with the first pick in the 1989 supplemental draft was a blunder, trading him in the third week of the 1990 season was a genius move. Troy Aikman was still figuring things out in the NFL, but he was clearly the better young quarterback, and Dallas chose to stick with him, trading Walsh to the New Orleans Saints and getting their first and third-round picks in 1991 and second-round pick in 1992 in return.
The Cowboys would use that third-round Saints pick to draft Erik Williams, and the giant-sized small college offensive tackle went on to become a four-time Pro Bowler and three-time All-Pro. The other picks were traded away in a series of deals, but even if you consider Williams alone and his eventual impact with the Cowboys, it’s clear to see who got the better end of things, and who ultimately made up for a boneheaded draft move.
8. WORST: HIRING BARRY SWITZER (1994)
They say nice guys finish last, but as Lenny Wilkens had proven back in his NBA coaching days, that isn’t necessarily true all the time. But Barry Switzer fit this trope to a T by the end of his coaching years in Dallas. He was hired in 1994 when the hard-nosed, always confrontational Jimmy Johnson left the team after his relationship with the other JJ (owner/GM/supreme overlord Jerry Jones) completely broke down.
At first, Switzer was winning games with the talented Cowboys, and he took them to another championship in the 1995 season, as they won Super Bowl XXX. But it was becoming clearer and clearer that the Cowboys, who also boasted of hard-partying, often-combustible personalities such as Michael Irvin and Charles Haley, missed Johnson’s disciplinarian approach and were veering out of control with the laissez-faire Switzer in charge. By the end of 1997, the Dallas Cowboys went a disappointing 6-10 just two years after their last Super Bowl win, and Switzer was gone, with his Cowboys teams having generally underachieved under his lax leadership.
7. BEST: MOVING ON UP IN THE ’74 AND ’75 DRAFTS (1974-75)
We did mention in here that the Cowboys had 20 straight winning seasons from 1966 to 1985. So how on earth were they able to draft first-overall in 1974 and second-overall in 1975? It all started in 1973, when the Cowboys traded disappointing, injury-prone defensive end Tody Smith and promising backup receiver Billy Parks to the Houston Oilers for their first- and third-rounders in 1974. With the Oilers going 1-13 in ’73, that gave Dallas the top draft pick in ’74, and they used that selection on Ed “Too Tall” Jones, a 6’9” defensive end who promptly made an impact as a sack machine. Their third-round pick acquired from the Oilers, Danny White, would replace Roger Staubach at QB in 1980, and he did a pretty good job at it.
Then there was the trade that sent Craig Morton, then languishing behind Staubach, to the similarly-struggling New York Giants midway through the 1974 season. Inexplicably, the Giants surrendered their 1975 first-rounder as part of the deal, and as they went 2-12 in 1974, the Cowboys were picking second in ’75. With that, Jones was joined in the defensive line by DE/DT Randy White, and both men are now in the Hall of Fame.
6. WORST: THE JOEY GALLOWAY DEAL (2000)
By the start of the 21st century, the once-mighty Cowboys were a middle-of-the-road NFL team. Troy Aikman was aging, and Michael Irvin, who likewise was no spring chicken, had suffered a career-ending injury in 1999. The Cowboys’ receiving corps still had Raghib Ismail, but Dallas needed another elite WR in their lineup, hence the decision to trade their 2000 and 2001 first-rounders to Seattle for Joey Galloway. His stats were down in 1999 due to a contract dispute that had him missing half the season, but he had otherwise passed the thousand-yard receiving mark in three of his first four seasons.
Galloway would retire in 2010 after 16 seasons and even more thousand-yard campaigns, but his time in Big D was, well, a big D of another kind – a disappointment. He missed all but one game in 2001 with an ACL injury, and while he played solidly from 2002 to 2004, his fat contract (second-richest for WRs at the time) was the epitome of albatross. Meanwhile, the Seahawks used their 2000 draft pick on Pro Bowl RB Shaun Alexander, and traded down in 2001 to get WR Koren Robinson, who put up similar numbers to Galloway from 2001 to 2003 at a fraction of the price.
5. BEST: USING A LATE-ROUND PICK ON ROGER STAUBACH (1964)
Roger Staubach looked like a potential NFL star quarterback in the making when he won the Heisman Trophy as a junior in 1963. But since he played for Navy and had a four-year military commitment to follow after graduation, that hurt his draft status in 1964 as a “future” pick; his color-blindness didn’t help his potential draft position either. Yet the Dallas Cowboys took a flyer in him in the tenth round of the 1964 draft, knowing full well that he would be a 27-year-old rookie when he’d finally get to play in 1969.
The Cowboys patiently waited for Staubach to arrive, and kept waiting for him to emerge as a star, as he sat behind the well-above-average Craig Morton in the 1969 and 1970 seasons. But when Morton struggled in 1971, coach Tom Landry decided to platoon both his QBs, and eventually promoted Staubach to a full-time starting job later that season. It was a great decision, as Staubach led the Cowboys to win Super Bowl VI, then to three more championship games, including another win at Super Bowl XII. What’s also remarkable is that he maintained a high level of play even as a 37-year-old in his final season in 1979, which was fairly rare back in his time.
4. WORST: PASSING ON RANDY MOSS (1998)
You had one job, Jerry Jones. Here’s an ultra-talented college wide receiver who makes no bones about how he wants to play for the Dallas Cowboys in the NFL, the team he grew up rooting for. You’ve got the eighth overall pick, and he’s got the talent, speed, and athleticism, as well as the eye-popping stats – 54 receiving TDs in two years at Marshall. Michael Irvin is still playing well, but at 31, he won’t be around forever, and Anthony Miller is even older at 32 and on the decline. He wants you to draft him, your scouts want you to draft him. But do you draft him?
Of course not! Jones was concerned about Randy Moss’ off-the-field issues, so he went ahead and drafted linebacker Greg Ellis instead with the eighth pick in the 1998 draft. Ellis was far from a bad player for the Cowboys, but he was no Randy Moss, who arguably became the NFL’s greatest wide receiver since Jerry Rice. Sure, Moss wasn’t always a saint during his 14-year NFL career, but the man has the receiving touchdown record, and the man is now a legend and a future Hall of Famer. Oh, and if you’re wondering, he never did get to play for the Cowboys.
3. BEST: HIRING TOM LANDRY AS THEIR FIRST HEAD COACH (1960)
A former NFL defensive back and punter who made the Pro Bowl once in his seven-year career, Tom Landry entered coaching in his second-to-last year season as a player, and created the now-ubiquitous 4-3 defense as the New York Giants’ defensive coordinator. The Dallas Cowboys liked his football IQ well enough to hire him as their first head coach in 1960, and the youthful coach then added a twist to the 4-3, coming up with the Flex Defense in an effort to slow down Vince Lombardi’s running game with the Green Bay Packers. Then he popularized the shotgun formation on offense in the mid-‘70s, as his Cowboys were sharing the limelight with the Pittsburgh Steelers as one of the NFL’s top two teams of the decade.
All in all, Tom Landry spent 29 long years coaching the Cowboys, and aside from innovating, he won a lot of games, ending his career with a 250-162-6 record and two Super Bowl wins. His firing after nearly three decades of loyal service created quite the outrage in Big D, though as Jimmy Johnson proved, he was far from being a shabby replacement.
2. WORST: THE ROY WILLIAMS DEBACLE (2008)
Sometimes, the Cowboys can work magic with midseason trades, as we’ve documented in this list. But sometimes, they could end up left holding the proverbial bag, just like what happened in 2008 when they traded future first-, third, and sixth-round picks to the moribund Detroit Lions in exchange for wide receiver Roy Williams. And it was more than just a chance for Dallas to have two players named Roy Williams in their lineup – Williams the WR was a Pro Bowler, and seemingly an ideal complement to Terrell Owens. (Who narrowly missed this list, in case you’re wondering.)
With Williams signed through 2014 on a rich six-year, $54 million deal, he was extremely unproductive alongside TO immediately after the trade. The year after, he remained in the shadows as undrafted backup Miles Austin replaced Owens following his release and enjoyed a breakout year. And in 2010, first-rounder Dez Bryant, despite his reserve status, outplayed Williams, who was released in the 2011 offseason. While none of the picks Dallas traded away for Williams became stars, he was, plain and simple, an overpaid bust for the Cowboys.
1. BEST: THE HERSCHEL WALKER TRADE (1989)
The Dallas Cowboys were playing with fire when they pulled off this trade early in the 1989 season, trading franchise running back Herschel Walker and a few draft picks to the Minnesota Vikings, and getting five journeymen and a TON of draft picks, most of them conditional first-to-third-rounders. The Vikings thought they were getting the man they needed to take them to the Super Bowl, while Cowboys fans had largely believed coach Jimmy Johnson, who had thought of the trade, was crazy. The team was struggling mightily, so why trade away one of your few certified stars for scrubs and future picks?
In the end, the Cowboys had the last laugh and then some, as a lot of those picks were used on key players in the 1990s dynasty in Big D. Although some additional trades and conditional cuts were involved with some of the picks, Dallas ended up with Emmitt Smith, Darren Woodson, Alvin Harper, and Dixon Edwards, among others. Smith and Woodson alone are good enough to make the trade look extremely lopsided in the Cowboys’ favor, and while Walker did help the Vikings for some time, we’ve yet to see them back in the Super Bowl.
Dallas, meanwhile, won three of them in the ’90s. ‘Nuff said.
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