Bill Belichick was one of the most popular assistants in New York during his 12-year stint with the team. He spent all of his time on the defensive side of the ball, taking over the defensive coordinator duties in 1985.
The year after he took over, the Giants won the Super Bowl. In six years as the defensive coordinator, the Giants had one of the most feared units in the NFL. They finished fifth, second, 13th (strike year), ninth, second and first in scoring defense in those years.
The 1990 Giants defense was legendary, and during the playoff run they held the vaunted 49ers offense to 13 points in the NFC championship, and then held Jim Kelly and the Bills to just 19 points. His game plan for the Bills is part of the NFL Hall of Fame.
Bill Parcells retired for health reasons after that season, and for some reason George Young, the GM at the time, had already named offensive coordinator Ray Handley as the eventual successor for Parcells and didn't budge when he promoted Handley to head coach.
After several years of defensive dominance, the Giants stiffed Belichick and he left the team to be the Browns head coach. How ironic is it that eventual Giants GM Ernie Accorsi hired Belichick as the Browns GM in 1991. If only he had joined the Giants a few years earlier.
Handley went on to coach two straight 6-10 teams and was fired. Although Belichick struggled with the Browns and you could argue that he may have done the same with New York, there is no denying the Giants were a more talented team than the Browns.
Another reason he likely would have succeeded with the Giants is that they loved him and would have gone to war for him, whereas in Cleveland he was not as popular, especially when he was chastised for releasing Bernie Kosar, a fan favorite.
Who's to say the Giants don't win another Super Bowl or two with Phil Simms and Bill Belichick calling the shots?
Hell, even Tom Coughlin was on the coaching staff that year and would have been a better hire than Handley. Coughlin went on to coach the expansion Jacksonville Jaguars and had some incredibly successful years there.
It's been 20 years since that 1991 offseason, and the Giants have only one ring in that time. Who knows how many more we could have with "The Hoodie" patrolling the sidelines.