20 Years Ago Today: Charles Woodson Became Jon Gruden’s First Draft Pick with the Raiders
Two decades ago today, a pivotal moment in Raiders history took place — one that would shape the franchise for years to come. On April 26, 1998, Charles Woodson, the electrifying cornerback out of Michigan, became the first-ever draft selection of new head coach Jon Gruden, ushering in a new era for the Silver and Black.
When the Raiders hired the then-34-year-old Gruden earlier that year, it marked a major shift for a franchise rooted in tradition but hungry for innovation. Tasked with restoring the Raiders’ mystique, Gruden wasted no time making an impact. With the fourth overall pick in the 1998 NFL Draft, the Raiders selected Woodson — a Heisman Trophy winner whose rare combination of athleticism, instincts, and playmaking ability made him one of the most coveted prospects in years.
Woodson’s arrival in Oakland immediately energized the fan base. Known for his physical style, supreme ball skills, and fierce competitiveness, Woodson embodied everything Al Davis valued in a defender. From the moment he stepped on the field, Woodson delivered, winning NFL Defensive Rookie of the Year honors after snagging five interceptions and forcing two fumbles in his first season.
Beyond the stats, Woodson helped reestablish the Raiders’ identity on defense. His swagger, toughness, and penchant for making game-changing plays fit perfectly with the franchise’s storied past. Under Gruden’s leadership — and with Woodson anchoring the secondary — the Raiders quickly transformed from perennial underachievers into legitimate contenders.
During Gruden’s first run as Raiders head coach from 1998 to 2001, the team posted two playoff appearances and a trip to the AFC Championship game. Woodson became a cornerstone of that resurgence, earning four consecutive Pro Bowl selections and two first-team All-Pro honors during Gruden’s tenure.
Though Gruden would famously be traded to the Tampa Bay Buccaneers before the 2002 season — and later defeat the Raiders in Super Bowl XXXVII — his first major move in Oakland remains one of his most significant. Drafting Woodson laid the foundation for both immediate success and long-term greatness.
Woodson’s legacy with the Raiders stretched across two stints. After leaving the team in free agency in 2006 and winning a Super Bowl with the Green Bay Packers, he returned to Oakland in 2013. Even at an advanced age, Woodson remained a force, mentoring young players and continuing to produce at a high level until his retirement after the 2015 season.
In all, Woodson’s NFL career spanned 18 seasons, 65 interceptions, and nine Pro Bowl selections. He was inducted into the Pro Football Hall of Fame in 2021, cementing his place among the greatest defensive players in league history.
Today, as the Raiders continue to search for a return to glory, the memory of Charles Woodson’s selection serves as a reminder of the kind of transformative talent — and leadership — that can change a franchise’s fortunes. Twenty years later, Gruden’s first draft pick remains one of the best in Raiders history.
