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The NFL season is underway, and my fantasy team is already in last place! As the season begins, there are a lot of interesting headlines, from Tom Brady’s debut as an announcer to Dak Prescott becoming the highest-paid NFL player. I got to thinking about some of the most remarkable negotiations in NFL history. These high-stakes negotiations offer some great lessons that you can take into your next deal.
Tom Brady: Sacrificing for the Greater Good
Let’s start with future Hall of Famer — and current Fox Sports color commentator — Tom Brady. One of the greatest quarterbacks of all time, he’s known not only for his seven Super Bowl rings, but also for his approach to compensation. Brady took several pay cuts throughout his career to help the New England Patriots build a stronger team around him. By doing so, he ensured that the organization had the salary-cap flexibility to sign and retain key players, contributing to its dynastic status.
Most of us are negotiating with those we live with, work with, and do business with. It’s imperative that we keep the bigger picture in mind. If we don’t, we can let short-term gains hamper long-term growth. In addition, short-term thinking can damage relationships and establish unwanted precedent. You’ll be better at creating long-term value and lasting relationships if you think about the big picture.
Dak Prescott: Know Your Value
Dak Prescott took a slightly unusual approach to become the highest-paid NFL player. His negotiation was very protracted, taking months to complete. But his story actually starts back in 2020, when the then-rising star was looking for a long-term, high-paying contract. The Cowboys were hesitant: Prescott hadn’t proven himself yet.
Instead of accepting a lower-value deal or holding out, Prescott bet on himself. He took the franchise tag (a tool an NFL team can use on one free agent player to lock them in at a set rate for a year). It paid off: In 2021, he signed a contract extension worth $160 million. This year, he signed another deal and became the NFL’s first $60-million-a-year player (over four seasons).
Understanding your value can give you the confidence to persist in the face of pressures during a negotiation. This is not about being inflexible, but rather protecting your value along the way.
Dallas Cowboys: Giving to Get
Since we’re talking about the Dallas Cowboys, let’s continue with a blockbuster trade made in the ’80s. Way before Herschel Walker was a politician, he was one of the most dominant running backs in the NFL, playing for the Cowboys. In 1989, the Minnesota Vikings were trying to make their first Super Bowl appearance in over a decade and felt they needed a powerful running back. They wanted Walker. It seemed unthinkable that the Cowboys would trade their Pro Bowl running back to Minnesota, but they did it.
In return, Dallas got five players and six future draft picks. That trade eventually involved 18 players who helped the Cowboys build a dynasty. Prior to the trade, the Cowboys ended the 1989 season, winning only one game. But that trade set them up to win three Super Bowls in the ’90s. The Vikings? They didn’t even make it back.
It’s tempting to ignore or dismiss an impossible ask during a negotiation. However, an impossible ask is also an opportunity to create an impossible get. The next time someone asks for something from you that seems impossible to give, pause and ask yourself, “What’s my impossible get?” Be creative, think big, and stretch your imagination. You might be able to parlay that into your own Super Bowl-esque victory.
Negotiating like an NFL pro isn’t about brute-force tactics — it’s about finesse. It means understanding the bigger picture, knowing your worth, and being open to opportunities. Whether you’re negotiating a salary, a business contract, or a major life decision, these NFL lessons apply to help you get better outcomes. As you watch the games this season, hopefully you appreciate that a lot of negotiating went into making them happen.
We Can Help You Negotiate Like an NFL Pro.
Negotiating like an NFL pro isn’t about brute-force tactics — it’s about finesse. It means understanding the bigger picture, knowing your worth, and being open to opportunities. Rely on Scotwork’s nearly 50 years of experience to help you make your goals.
