Ben Watson thought he hit the jackpot. The second-team All-SEC tight end was selected in the first round of the 2004 NFL Draft by the defending Super Bowl champion New England Patriots. He was about to catch passes from a young Tom Brady during the early stages of what would become one of the greatest dynasties in professional sports. NFL life was kicking off in a big way, but first, there was a contract to negotiate.

The Patriots wanted their first-round pick to sign an uncommon six-year deal. Watson decided to hold out, hoping for a more favorable rookie contract—a standard practice in the NFL at the time, before the implementation of a rookie wage scale. However, the Patriots didn’t take kindly to his decision. Watson told BET that he received calls from the organization that were “derogatory and unprofessional.”

After holding out of training camp for 18 days—back when teams practiced twice daily—and firing his first agent, Watson eventually signed the six-year deal. The pressure had become too much for the rookie, who just wanted to play football.

“I, having no leverage, just wanted to go play,” Watson said. “I [didn't] want to cause too much of a stir.”

When Watson finally reported to camp, Brady had some reassuring words for him.

“He was like, ‘We all understand,’” Watson recalled. “‘All of us have to deal with our battles when it comes to contracts. We’re happy you’re here now, and we’re all behind you.’”

Watson went on to play 15 seasons in the NFL and learned many lessons along the way. One of his earliest realizations was how heavily his eight-figure contract would be taxed. Being in the top federal tax bracket—35 percent at the time—was just the beginning. When pro athletes play road games, their income is subject to that state’s tax rate, and they may also face an “entertainer’s tax.”

“Certain cities or jurisdictions have taxes for performers that come to their cities,” Watson explained. “It’s not much different than when a musician or a performer has a concert. There are certain taxes and fees that jurisdictions have that athletes sometimes fall under.”

After seven years and a Super Bowl championship with the Patriots, Watson signed with the Cleveland Browns in 2010. There, he became active in the NFL Players Association (NFLPA) as an alternate representative for the team. In 2012, teammate Scott Fujita encouraged him to join the NFLPA’s executive committee, where Watson was elected and re-elected every term until his retirement.

“Me being involved was understanding that, number one, player rights don’t just come,” Watson said. “They have to be taken.”

While salary is often the primary focus during collective bargaining negotiations between players and league ownership, other benefits are equally critical. For example, players who are on an active roster, injured reserve, or physically unable-to-perform list for at least three games over three seasons qualify for full medical coverage for themselves and their dependents.

Watson retired from football in 2020 and transitioned into television as a college football studio analyst on ESPN’s SEC Network. He is also taking advantage of benefits from his playing career to further his education.

“I’m in school right now, getting a master’s in public administration and public policy from American University online,” Watson said. “I’ve been in for about a year now, and the NFL, through our benefits package, reimburses continuing education.”

Contracts and collective bargaining agreements are filled with legal jargon—procedures for arbitration, guidelines for injuries—but at their core lies a fundamental struggle between management and labor. In professional football, this dynamic is amplified by high stakes: players endure dozens of full-speed collisions weekly for at least five months each year while generating billions of dollars in revenue for team owners. The NFL remains the most profitable sports league on earth and has been so since the late 1970s.

“As players, you’re trying to get as many advances as you can in a short period of time,” Watson said. “While still trying to pass on a passion and understanding of what it took to get to a certain point and what it’s going to take to get to the next point.”