The 49ers, who lost Charvarius Ward in free agency last offseason and struggled in their secondary during 2025, could benefit from adding the 6-foot-4, 210-pound playmaker. Woolen, 26, has recorded 12 interceptions and 53 pass defenses in 64 career games and would give San Francisco a significant upgrade at outside cornerback.
Kay predicts Woolen will sign a four-year, $55 million contract, which could create an expensive but formidable cornerback group alongside Deommodore Lenoir, who is already on a five-year, $88.88 million deal with the team.