The first player to accumulate five Super Bowl Rings was Charles Haley, who collected the first two of those finger jewelry as a San Francisco 49er.

When the Dallas Cowboys acquired Charles Haley in August 1992, they were getting a proven champion still in his physical prime. Haley had already won two Super Bowls and earned three Pro Bowl nods in San Francisco, but friction with head coach George Seifert made him available via trade. Jimmy Johnson seized the opportunity, bringing in the explosive edge defender to serve as the missing, mean-spirited catalyst for a rising contender.

Haley converted seamlessly into the defensive end spot in Dallas's 4-3 scheme. Though his intense, unvarnished personality could cause friction behind closed doors, his on-field impact was immediate and transformative. He injected an unquestioned edge into the defensive front, demanding perfection from teammates and giving the Cowboys the premier pass-rushing threat they needed to get over the playoff hump.

Over his first four seasons in Big D, Haley helped usher in a golden era, capturing three Super Bowl titles (XXVII, XXVIII, XXX) and becoming the first player in NFL history to win five Super Bowl rings. He earned two Pro Bowl selections in silver and navy, pairing them with a First-Team All-Pro nod in 1994. In both of those Pro Bowl campaigns (1994 and 1995), he posted double-digit sack totals, wreaking havoc on opposing protection schemes in big-game moments.

Severe back issues and personal family matters led to brief retirements near the end of his tenure, though he returned to help secure his third ring in Texas before retiring after the 1996 season. He later mounted a brief comeback with the 49ers in 1999, but his legacy as the ultimate championship catalyst was already secure.

Haley had 34.0 sacks, 172 combined tackles, six forced fumbles, and four fumble recoveries with Dallas.