Charles Woodson is set to follow Tom Brady into NFL ownership, purchasing a 0.1% stake in the Cleveland Browns. According to reports from The Athletic and Cleveland.com, Woodson will pay $5 million to Browns owner Jimmy Haslam, valuing the team at $5 billion.

The deal comes with conditions, mirroring those Brady faced when he acquired a minority stake in the Las Vegas Raiders. As an analyst for Fox Sports, Woodson must adhere to broadcasting restrictions. These rules prevent him from accessing other teams' facilities, practices, and production meetings with coaches, players, and executives of teams whose games he is covering. Brady faced similar conflicts of interest as both an owner and broadcaster, although the NFL lifted some restrictions for Super Bowl LIX.

Brady's share of the Raiders is significantly larger at 5%, and he had a more active role in football operations. It remains unclear whether Woodson will have similar responsibilities with the Browns. Additionally, Woodson must remove his name, image, and likeness from other business interests, notably his "Charles Woodson's Intercept" wine label. Ironically, Brady's Raiders have previously served this wine at a luxury tailgating event.

Haslam and Woodson reportedly connected last year, leading to the agreement. Woodson, a native of Fremont, Ohio, is joining a growing trend of former athletes investing in teams. His history with Brady includes being on opposite sides of the infamous "Tuck Rule" game, where Woodson appeared to force a fumble from Brady, which was controversially overturned.

Woodson and Brady were also teammates at Michigan during the 1997 national championship season, though Brady was not a starter at the time. Woodson's resume includes winning the Heisman Trophy, Super Bowl XLV with the Green Bay Packers, the 2009 Defensive Player of the Year award, and nine Pro Bowl selections. He was inducted into both the College Football Hall of Fame in 2018 and the Pro Football Hall of Fame in 2021.