4. 1994 Cleveland Browns
Team record: 11-5
Belichick sat there and took his lumps during the first three seasons of his tenure in Cleveland. Quarterbacks were dropping like flies during those three initial seasons and the roster flat out wasn’t good enough to do much of anything.
In 1994, however, Belichick was finally given a bit of stability as Vinny Testaverde started 13 games that season. With his man under center, Belichick guided them to their first double-digit winning season in a number of years.
A Super Bowl berth was a bit of a stretch, but not for Belichick. In the opening round of the playoffs, he led the Browns to a win over — ironically enough — the New England Patriots, in the Wild Card Game.
Belichick has relished in playoff football, but the Browns were unceremoniously eliminated in the divisional round against the Pittsburgh Steelers, losing by 20 points.
All in all, Belichick believed his time in Cleveland was just getting started. That ’94 team had the best defense in the league by far, holding opposing squads to just 12.8 points per game. If given more time, Belichick could’ve kept the Browns relevant for decades to come.