1. Cutting Lawyer Milloy (2003)
This is a move that all Pats fans remember as really the beginning of two decades filled with surprising Belichick decisions.
Cutting Lawyer Milloy truly set the tone for the entire Patriots dynasty and sent a clear message: Belichick did not care how successful you had been with the team or how much you were loved in the locker room — no player was bigger than the system itself.
Lawyer Milloy was a seven-year Pats veteran, four-time Pro Bowler, Super Bowl Champion, and team captain. Milloy was even the first person to embrace Belichick after Vinatieri’s kick went through the uprights to help the franchise capture its first Lombardi trophy.
If being team captain and locker room favorite wasn’t enough, Lawyer was known to be extremely close with star QB Tom Brady, even sharing the movie screen with him in “Stuck On You.”
The season after he was cut, Milloy started all 16 games and was a Pro Bowler. He would be picked up promptly by the division-rival Buffalo Bills.
After this earth-shattering decision, ESPN analyst Tom Jackson infamously announced to the world that the Patriots players hated Belichick. The Pats ironically faced Milloy and the Bills in Week 1 and ended up losing 31-0. This loss, of course, added to the criticism of Belichick’s decision, but it was he who got the last laugh after the team capped off the season with another Super Bowl victory.
Other notable shocking Bill Belichick moves
- Letting Adam Vinatieri walk in 2006
- Trading Chandler Jones in 2016
- Trading both Matt Cassel and Mike Vrabel in 2009
- Trading Deion Branch in 2006