Allie Sherman (New York Giants)
Few coaches could’ve asked for a more perfect situation than the one Allie Sherman got. The New York Giants were a stacked football team in the early 1960s. They had Hall of Fame and perennial Pro Bowl talent everywhere. Y.A. Tittle, Del Shofner, and Frank Gifford on offense. Sam Huff, Eric Barnes, and Jimmy Patton on defense. They were one of the most complete teams in franchise history.
So for them to reach three-straight NFL championship games from 1961 to 1963 and lose all three? That has to fall at the feet of the head coach. What makes it even worse is how they lost them. They scored seven points total in two games against the Vince Lombardi Packers. Then they self-destructed against a Chicago Bears team that they were frankly better than.
If that weren’t bad enough, towards the end of his run in New York, Sherman secured the services of future Hall of Fame quarterback Fran Tarkenton. The best he managed was two 7-7 seasons. Sherman was fired in 1969.