When it comes to making a big splash in trades, the Cowboys have made some historic moves.
The big news in Dallas over the weekend did not come from a move Jerry Jones made as that honor belongs to Dallas Mavericks GM Nico Harrison after he traded the face of his franchise, Luka Doncic, to the Los Angeles Lakers. While this huge head-scratching moment doesn’t come from the Dallas Cowboys, it doesn’t stop people from taking a shot a Jerry Jones.
This is dirty work… pic.twitter.com/YZ1g48M6SG
— Newy Scruggs (@newyscruggs) February 3, 2025
Sorry Mavs, you guys are on your own with that one.
People won’t waste an opportunity to criticize the Cowboys owner/GM, but when you’re talking about blockbuster trades, Jones is sitting pretty as he’s done more good than bad in this department. Yes, the Trey Lance and Jonathan Mingo deals are fresh in our minds and most people are still caught up on the fifth-round draft capital with the Amari Cooper trade, but when you think about it, the Cowboys aren’t as terrible as some think when it comes to making deals.
What are the team’s most successful trades? Which ones are their worst? In light of the Mavs’ big splash, let’s take a look at some of the biggest deals the Cowboys have made throughout their history.
BEST TRADES
Trading away Herschel Walker to the Vikings
Most everyone knows all about this one. The Cowboys were terrible in 1989 so they leveraged their best player for a slew of draft picks that Jimmy Johnson turned into to valuable assets. There was also a lot of wheeling and dealing that shuffled around some of those picks, but the return the Cowboys got from that trade is as follows:
- Emmitt Smith – Hall of Fame
- Darren Woodson – Hall of Fame finalist
- Russell Maryland – 10-year starter, Pro Bowler
- Kevin Smith – eight-year starter
That’s a pretty good haul. This trade known as “The Great Train Robbery” remains not only the best trade in Cowboys history, but in NFL history as well.
Trading up to select Tony Dorsett
Both the Cowboys Hall of Fame running backs were acquired through a big trade. In 1977, the Cowboys snookered the Seattle Seahawks out of the No. 2 overall pick that the Cowboys used to take Pittsburgh star running back Tony Dorsett. In return, the Seahawks got the 14th overall pick and three second-rounders.
The Seahawks got a slew of picks, but nothing manifested from them compared to the career that Dorsett had. When he retired, he was second all-time on the NFL rushing list, trailing only Walter Payton.
Trading for Charles Haley
Everything came together for the Cowboys in 1992, and the final piece was acquiring pass-rushing stud Charles Haley from the San Francisco 49ers for a second- and third-round pick. Despite three Pro Bowl seasons (six seasons total) and two Super Bowl wins with the 49ers, Haley had become a headache, allowing the Cowboys to swoop in and grab him for a discounted price.
Haley immediately bolstered the Cowboys’ defensive line and was part of a defense that helped the Cowboys win three Super Bowls in four years. Even more satisfying is that he helped them beat his former team twice in the NFC Championship when Dallas and San Francisco were the two top teams in the league. Haley was elected to the Hall of Fame in 2015.
WORST TRADES
Trading for Roy Williams
The Cowboys wanted to give Tony Romo another receiving talent opposite Terrell Owens so they traded away a first-round pick, third-round pick, and sixth-round pick to the Detroit Lions for Roy Williams. The 27-year-old receiver was just a couple of years removed from a Pro Bowl season where he had over 1,300 receiving yards.
Sadly, he never was that same player in Dallas averaging just 33 yards per game. Making matters even worse is the Cowboys gave Williams a six-year, $54 million extension. He was released in 2011 after just two and a half seasons with the Cowboys.
Trading for Joey Galloway
After Michael Irvin suffered a career-ending spinal cord injury, the Cowboys tried to give Troy Aikman one last chance to make a run by making a trade with the Seahawks for their star receiver Joey Galloway. Dallas gave up two first-round picks to get Galloway.
While the plan seemed okay in theory, everything blew up in their face. Galloway got hurt in his Cowboys debut and was lost for the year with a torn ACL. When he returned the following year, Aikman had retired, leaving the offense in dire straits. With older players leaving and no premium draft capital to help replenish the team, it set the stage for some disappointing seasons at the turn of the century.
Trading up to get Morris Claiborne
The Cowboys are stingy with premium draft capital these days, but as you can see from these examples, that wasn’t always the case. In 2012, the team gave up a second-round pick to move to the No. 6 overall pick to select LSU cornerback Morris Claiborne.
Like the others, the idea wasn’t terrible and Claiborne was highly regarded coming out of college, but the outcome wasn’t favorable. Claiborne dealt with numerous injuries and never lived up to the hype. Additionally, we learned through the grapevine that the Cowboys’ second-round pick would have likely been eventual All-Pro linebacker Bobby Wagner.
