1. Bill Belichick, Head Coach
The No. 1 former Cleveland Brown to go on and win some Super Bowl jewelry is none other than former head coach Bill Belichick. After winning two Super Bowls as the defensive coordinator for the New York Giants and Bill Parcells, the Browns hired Belichick to be their head coach. He held that title for five seasons and was the final coach in Cleveland before the team moved to Baltimore.
During his stretch with the Browns, they struggled to get wins as he had a losing record in four-of-five seasons. In 1994, Belichick did lead them to an 11-5 mark, but that proved to be the anomaly as they finished 36-44 under his watch.
Belichick was supposed to coach the team in Baltimore and was assured he would be retained by owner Art Modell. However, he changed his mind and fired the head coach shortly after the 1995 season.
The former Browns coach went on to be an assistant with the New England Patriots and New York Jets before taking the head coaching job in 2000 with the Patriots. Now serving in that role for 19 seasons, Belichick has a record of 225-79 for them and is set to be coaching his ninth Super Bowl — and looking for win No. 6.
Belichick is going to go down as the best coach in NFL history considering the insane stretch of success he’s had with the Patriots, which makes Browns fans sick to this day to think about.