Charles Haley has five Super Bowl rings.
Haley earned his first two championships with the San Francisco 49ers, winning Super Bowl XXIII after the 1988 season and Super Bowl XXIV after the 1989 season. He then joined the Dallas Cowboys and helped them win three more titles: Super Bowl XXVII, Super Bowl XXVIII, and Super Bowl XXX.
Haley was a versatile and disruptive defender. He began his career as an outside linebacker in San Francisco's 3–4 defensive system, then became a defensive end after the 49ers shifted toward a 4–3 alignment. With Dallas, his pass-rushing ability became an important part of the Cowboys' early-1990s dynasty.
For many years, Haley was the first player to win five Super Bowls. Tom Brady later surpassed him, eventually winning seven as a player, but Haley remains second on the individual list. Another frequent source of confusion is the difference between team championships and a player's rings: Haley's five came from two franchises, not five victories with one team. He started all five championship games in which he played.