The Dallas Cowboys were one of the best teams at wheeling and dealing in the early 90’s, but the trend stopped.
What happened to the maverick owner Jerry Jones, who put his money where his mouth was and went out and bought the best players?
Is it old age, lack of urgency, or too many chefs in the kitchen?
One thing is for sure: The Dallas Cowboys do not seem to care about winning by paying free agents; instead, they draft to fill needs.
Let’s look at the past and see where the wheeling and dealing trend started and stopped for the Dallas Cowboys.
Jerry’s First Big Acquisition
Everyone knows Jerry Jones bought the Dallas Cowboys in 1989. One of the first moves was getting rid of legendary Coach Tom Landry.
The second move was making a big trade.
On October 12, 1989, the Dallas Cowboys made a trade with the Minnesota Vikings, sending running back Herschel Walker, a third and 10th-round pick from the Cowboys in 1990, a fifth-rounder from the Chargers, and a third-round pick from the Cowboys in 1991.
The Chargers received running back Darrin Nelson.
The Dallas Cowboys received defensive end Alex Stewart, linebacker David Howard, linebacker Jesse Solomon, and cornerback Issiac Holt first, second, and sixth-round picks in the 1990 NFL Draft, first and second-round picks in 1991, and first, second, and third-round picks in the 1992 draft.
This was a massive trade made by the wheeling and dealing Jerry Jones.
This trade brought the Cowboys future players such as Emmitt Smith, Russell Maryland, Stan Smagala, Danny Stubbs, Alonzo Highsmith, Kevin Smith, and Darren Woodson.
It’s not a bad haul for a running back who did not amount to much in Minnesota.
On September 25, 1990, Jerry Jones made another trade. The Cowboys received the New Orleans Saints’ first—and third-round picks in the 1991 NFL Draft and a second-rounder in 1992 in return for quarterback Steve Walsh.
In the third round, the Cowboys picked up tackle Erik Williams.
The Next Big Trades for the Cowboys
On February 14, 2000, the Dallas Cowboys traded for wide receiver Joey Galloway from the Seattle Seahawks. In exchange, the Seahawks received first-round draft picks from the Cowboys for both the 2000 and 2001 NFL drafts.
On March 22, 2004, the Cowboys traded Joey Galloway to the Tampa Bay Buccaneers in return for wide receiver Keyshawn Johnson.
On October 14, 2008, the Cowboys acquired WR Roy Williams and a 2009 seventh-round pick from the Detroit Lions in exchange for first, third, and sixth-round draft picks in 2009.
It’s not Jerry’s best work, but it’s a trade nonetheless.
On May 9, 2014, the Cowboys received a second-round pick in the 2014 NFL Draft from the Washington Redskins, who received a second and a third-round pick in 2014.
This second-round pick became DeMarcus Lawrence.
On October 22, 2018, one of the best trades made by Jerry Jones occurred. The Cowboys received wide receiver Amari Cooper from the Oakland Raiders, who, in return, received a first-round pick in the 2019 NFL Draft.
These were big-time trades that showed Jerry Jones’s wheeling and dealing when trading for established players. He didn’t send fourth-round picks for players who were terrible or didn’t see the field.
It’s as if other front office members stepped in and stopped the big-time trades Jerry Jones is used to making. Once Stephen Jones became a more significant presence in the organization, these trades stopped, and penny-pinching became a trend.
Splash Free Agents
Trading was not the only thing Jerry Jones would have done in the past. He would also sign superstar free agents.
Jerry Jones would put the rest of the NFL on notice with the free agent signings in the past. These players were major contributors and made a lasting impact on the team.
The first was signing superstar cornerback Deion Sanders.
After years of competing against him as a member of the Atlanta Falcons and the 49ers, Jones was tired of facing the player and decided to bring him to Dallas.
The Cowboys had lost to Sanders and the 49ers in the 1994 NFC Championship Game. The following season, they signed him to a seven-year, $35 million contract, ensuring he could no longer be a threat to them.
The next best signing was early on in Jerry’s tenure as owner. A well-known Cowboys tight end Jay Novacek.
The history of great Cowboys tight ends features Jay Novacek, who joined the team in 1990. He became a key player and a reliable target for quarterback Troy Aikman.
A five-time Pro Bowler and one-time All-Pro, Novacek won three Super Bowls with the Cowboys, finishing his career with 339 receptions, 3,576 yards, and 22 touchdowns.
He ranks third all-time among Cowboys tight ends in receiving yards, behind Doug Cosbie and Jason Witten, and is remembered as one of the team’s best free-agent signings.
You cannot have Jerry Jones’ best hits without listing Nate Newton.
Nate Newton was a free agent from the then-defunct USFL, where he played for the Tampa Bay Bandits.
He spent 13 of his 14 NFL seasons with the Dallas Cowboys, earning six Pro Bowl selections and winning three Super Bowl titles.
As a key member of the Cowboys’ offensive line, he played a significant role in supporting Emmitt Smith and contributing to the team’s success in the 1990s.
These acquisitions show that Jerry Jones was not afraid to take risks. The only problem is that the last big trade was for Amari Cooper in 2018.
After that trade, the Cowboys’ front office seemed to become much more weary of trading and signing big-time free agents.
The early years were great because the salary cap was not an issue. Understanding and abiding by the salary cap is a must, but it seems other teams around the league know how to circumvent the cap and make their teams better.
The Dallas Cowboys and the Joneses seem lost because they cannot spend money at will and must abide by strict cap regulations. Taking more risks would be beneficial, but the younger Stephen Jones seems adamant about saving money.
Maybe this offseason will be different, and the Cowboys will spend some of the cap they can create.
Looking back on the past shows that the Cowboys know how to do the wheeling and dealing to get superstars, but only time will tell if the trend starts back up.