As a guard for the Raiders, Upshaw quickly established himself as a cornerstone of the team's offensive line. His tenure with the Raiders spanned 15 seasons, during which he played in 217 games. Upshaw's presence on the field was instrumental in the Raiders' success during the late 1960s and 1970s. He was part of the team that won two Super Bowl titles, Super Bowl XI and Super Bowl XV, and three AFL/AFC Championships. His ability to protect the quarterback and open up running lanes was a critical factor in the Raiders' offensive strategy.
Upshaw's excellence on the field was recognized with numerous accolades. He was selected to the Pro Bowl seven times and was named an All-Pro five times. His leadership qualities were evident as he served as the team captain for several years. In 1987, his achievements were immortalized with his induction into the Pro Football Hall of Fame, making him the first player to have played guard exclusively to receive this honor.
Beyond his playing career, Upshaw's influence extended into the administrative side of professional football. In 1983, he became the executive director of the National Football League Players Association (NFLPA). In this role, he was a staunch advocate for players' rights and worked tirelessly to improve their working conditions. Under his leadership, the NFLPA secured significant gains for players, including free agency and improved benefits.
Upshaw's tenure as executive director was marked by his negotiation skills and his ability to navigate the complex landscape of labor relations in professional sports. He played a crucial role in the negotiations that led to the 1993 Collective Bargaining Agreement, which introduced the salary cap system and free agency, fundamentally changing the business of professional football.
Throughout his career, both as a player and an executive, Upshaw was known for his leadership and his ability to bring people together.
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