Bud Grant – Minnesota Vikings (IV, VIII, IX, and XI) Three of the four head coaches with four Super Bowl losses are enshrined in the Pro Football Hall of Fame, with Grant the first one. His Vikings’ teams fell over an eight-season span, with only his Super Bowl IX squad being within single digits in the fourth quarter before it lost to the Steelers 16-6. His other teams fell 23-7 to the Kansas City Chiefs (IV), 24-7 to the Miami Dolphins (VIII) and 32-14 to the Oakland Raiders (XI) Don Shula – Baltimore Colts (III), Miami Dolphins (VI, XVII, and XIX) Shula is enshrined in the Pro Football Hall of Fame as the winningest coach in NFL history and a two-time Super Bowl champion, including his 1972 team that is the only one to finish unbeaten. But he also was the Colts coach when they fell to the New York Jets 16-7 in the biggest point-spread upset (18) in Super Bowl history, and lost three times with the Dolphins: 24-3 to the Dallas Cowboys (VI), 27-17 to Washington (XVII) and 38-16 to the 49ers (XIX). Marv Levy – Buffalo Bills (XXV, XXVI, XXVII, and XXVIII) The Bills teams that suffered a record four Super Bowl losses in a row played under Levy, who’s also enshrined in the Pro Football Hall of Fame. Their 20-19 defeat to the Giants in Super Bowl XXV is remembered most for Scott Norwood’s 47-yard field goal attempt that sailed “wide right” with only four seconds remaining. The Bills then lost in succession to Washington 37-24 and the Cowboys 52-17 and 30-13. Dan Reeves – Denver Broncos (XXI, XXII, and XXIV), Atlanta Falcons (XXXIII) Reeves’ Broncos squads, despite having Hall of Fame quarterback John Elway, lost three Super Bowls in a four-season span, and their 55-10 defeat to the 49ers on Jan. 28, 1990 is the most-lopsided in the game’s history. Add in the earlier losses – 39-20 to the Giants (XXI) and 42-10 to Washington (XXII) despite having a 10-0 lead after the first quarter – and the 18 Broncos’ players who participated only in those three Super Bowls were outscored 136-40, a 96-point point differential that is the worst in history. Reeves had it worse, though, going on to tie for the most Super Bowl losses by a coach, falling with the Falcons while Bennett earned his fifth defeat as a player.