Which player has lost 5 Super Bowls in a row?

The final game of every NFL season is been the Super Bowl since 1966. It was part of a merger agreement between the NFL and the American Football League (AFL) which justifies its first name the AFL-NFL World Championship Game. Lamar Hunt, owner of the Kansas City Chiefs first thought of the term Super Bowl in the mid-1960s. We have identified each Super Bowl with Roman numerals since the fifth edition in 1971. The Green Bay Packers lifted the first two Super Bowls while The Jets were the first AFL team to win a Super Bowl. The Trophy we see the winners lift is called the Vince Lombardi Trophy, named after the Packers coach who won the first two Super Bowls.

The Super Bowl is one of the most watched sporting events with the viewership being mostly domestic. Tom Brady who has seven championship rings sits on top of the most championships won by a player list. Marv Fleming of the Packers was part of the first two Super Bowl-winning squads, he also went on to win two more rings with the Miami Dolphins a few years later. While we discuss the winners, there were plenty of players who made it to the Super Bowl but could never lift the trophy.

Player With 5 Super Bowl Losses in a Row

Gale Gilbert

Gale Gilbert is the only player to be appearing in five straight Super Bowl losses. The quarterback played a total of eight seasons in the NFL playing for three franchises. He signed with the Seattle Seahawks as an unstaffed agent in 1985. On moving to the Buffalo Bills in 1989, Gilbert and the Bills advanced to four Super Bowls (XXV-XXVIII) in a row, losing all of them. Gilbert switched teams and signed with the Chargers in 1994. San Diego Chargers and Gilbert in his first year there, lost the Super Bowl XXIX making Gilbert lose five straight Super Bowls. Gilbert played his last season in the NFL the following year where the Chargers lost to the Colts in the wild card round.

Some More Players with Multiple Super Bowl Losses

Alongside Gilbert, there are a few others who have suffered multiple Super Bowl losses. Cornelius Bennett was also a part of the Buffalo Bill's straight four losses from 1991 to 1994. Furthermore, the linebacker went on to play for the Atalanta Falcons who lost the Super Bowl XXXIII, 34-19 against the Denver Broncos.

Glenn Parker the offensive linebacker was also part of the same Bills squad as Gilbert and Bennett. After losing in four straight Super Bowls with the Bills, he joined the New York Giants. Parker appeared in what would be his fifth Super Bowl seven years later in the 35th edition, losing 34-7 to the Ravens.