Facebook Pixel

    Best Dallas Cowboys Free Agent Signings of All Time: From Terrell Owens to Deion Sanders

    The Dallas Cowboys are a historic franchise with a rich championship tradition. And although they are not known for much of it now, the team has made many impactful additions in free agency throughout the years.

    Despite Dallas’ tight-to-the-vest approach in recent memory, the Cowboys may not have won some of their most recent Super Bowls without a few of these important additions.

    PFSN NFL Playoff Predictor
    Try out PFSN’s FREE playoff predictor, where you can simulate every 2025-26 NFL season game and see how it all shakes out!

    Ranking the Greatest Free Agency Additions in Dallas Cowboys’ History

    Cowboys owner Jerry Jones was once known for wheeling and dealing. The former oil tycoon was unafraid to take a chance at a massive payout, and that translated to his NFL life as well.

    While that strategy has tempered a bit over the last few years, it didn’t erase the past home runs he hit in free agency.

    Let’s take a deeper look at the five greatest Cowboys signings of all time!

    5) Terrell Owens

    Kicking off the list is a big-name wide receiver who had an ever-bigger personality. Terrell Owens was first a member of the Cowboys’ two biggest rivals: the San Francisco 49ers and Philadelphia Eagles.

    Before joining the team, he infamously disrespected the midfield star, which set up an interesting dynamic when Owens got to Dallas. However, once Owens got on the field and began to produce in a Cowboys uniform, a lot of that was forgiven by the Cowboys Nation.

    Owens joined the Cowboys ahead of the 2006 season after two seasons with the Eagles. He only spent three seasons in Dallas due to clashes with the coaching staff and the front office. However, during his tenure, he had every bit of the impact on the field they had hoped he would.

    Owens only missed one game during his time in Dallas, finishing with 235 receptions, 3,587 yards, and 38 touchdowns as Tony Romo’s No. 1 weapon.

    4) La’Roi Glover

    Much like the man listed above him, La’Roi Glover didn’t provide a Super Bowl title to the Cowboys, but his contributions on the field cannot be overstated.

    With stops in Oakland and New Orleans before signing with the Cowboys, Glover was well-traveled before settling in Dallas. From there, he found stability and played the best football of his career.

    In his four years with the Cowboys, Glover didn’t miss a game and finished with a Pro Bowl nod in all four seasons, as well as two All-Pro selections.

    Glover finished his tenure with 21.5 sacks and 32 tackles for loss while solidifying himself as one of the veteran leaders of a tough defensive group. He’s remembered as one of the very best signings Jones and Co. ever pulled the trigger on.

    3) Nate Newton

    Nate Newton wasn’t just a regular old free agent coming from an NFL team; he came from the then-disbanded USFL, where he played for the Tampa Bay Bandits until the league folded.

    Newton spent 13 of 14 seasons in the NFL with Dallas and finished with six Pro Bowl selections and three Super Bowl titles. He was a staple in the middle of the Cowboys’ offensive line and had the imposing physical presence needed to lead Emmitt Smith and Co. through their reign in the 1990s.

    MORE: Ranking the Best Dallas Cowboys Quarterbacks of All Time

    The Cowboys were known for their tremendous offensive linemen throughout their championship runs, and Newton’s free agent signing was another pivotal piece needed to secure that reputation.

    2) Jay Novacek

    The history of great Cowboys tight ends is well-documented. While players such as Jason Witten receive a lot of attention, Jay Novacek isn’t soon forgotten either.

    Novacek signed with Dallas in 1990 and became a staple in the offense and a security blanket for Troy Aikman. He finished his career as a five-time Pro Bowler and a one-time All-Pro selection. Novacek won three Super Bowls with Dallas, finishing with 339 receptions for 3,576 yards and 22 touchdowns.

    Novacek is third all-time among tight ends in Cowboys receiving, trailing only Doug Cosbie (3,728) and Witten (12,977), setting up what was one of the best free agent signings the Cowboys ever made.

    1) Deion Sanders

    The No. 1 spot belongs to Prime Time himself, Mr. Deion Sanders. When Sanders’ huge personality came to America’s Team, it was everything they had hoped for.

    From years of facing him while a member of the Atlanta Falcons and 49ers, Jones had enough of facing the man and instead brought him to Dallas.

    The Cowboys lost to Sanders and the 49ers in the 1994 NFC Championship Game. The next season, they signed him to a seven-year, $35 million deal, ensuring he could no longer hurt them.

    FREE: Subscribe to PFN’s NFL Newsletter

    Sanders played five seasons for the Cowboys, winning one Super Bowl, totaling 14 interceptions, and was an All-Pro in four of those five seasons.

    Sanders came in and changed the way offenses could attack the Cowboys’ defense. He was electric on special teams and even spent time as a wide receiver catching passes from Aikman.

    Sanders truly did it all and signals the last true superstar signing Jones and Co. went all in for, making him the best Cowboys free agent signing of all time.

    2026 NFL Mock Draft Simulator

    The PFSN Mock Draft Simulator features hundreds of prospects, scouting reports, and free trades -- jump into the mock draft machine and get ready for the 2026 NFL Draft.

    2026 NFL Draft Big Board Builder

    PFSN’s free NFL Draft Big Board Builder allows you to rank every prospect in the NFL Draft and share it with the world.

    2025 NFL Playoff Predictor

    PFSN's 2025 NFL Season and Playoff Predictor is a tool that allows you to play out various weekly scenarios to see how the NFL playoff picture changes with each scenario.

    NFL Offseason Manager

    Do you think you can manage your favorite team’s roster better than the real-life general managers? PFN's Offseason Manager is here to help you prove it.

    Commanders Announce Terry McLaurin, Jacory Croskey-Merritt Injury Updates on Friday for Week 10

    The Commanders will face the Lions in Week 10. Here is the latest update on the injuries to Terry McLaurin and Jacory Croskey-Merritt.

    Rams Announce Important Roster Decision for Week 10 Matchup vs. 49ers

    With a 6-2 record, the Los Angeles Rams find themselves tied for first in the NFC West and they want to maintain the stronghold with this change.

    Raiders Announce Massive Coaching Change After Week 10 Loss vs. Broncos

    The Las Vegas Raiders had a tough night on special teams against the Denver Broncos on Thursday night. It was enough to push Carroll to make a move.

    How Zak Kuhr Became the Patriots’ Interim Defensive Coordinator

    After Terrell Williams’ cancer diagnosis, Zak Kuhr stepped up as the Patriots’ interim defensive coordinator and has led the defense impressively so far.
    Join the Conversation!

    LEAVE A REPLY

    Please enter your comment!
    Please enter your name here