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There are plenty of opportunities to second-guess trades Bill Belichick has made during his time with the New England Patriots.
Saving you the click. In no particular order
1. Trading Up In 2006 NFL Draft To Select Chad Jackson
2. Giving Away Top Draft Capital For Mohamed Sanu
3. Patriots Get Next To Nothing For Chandler Jones
4. Derrick Burgess Trade Turns Into A Flop
5. Star Wideout Chad Ochocinco Flames Out With Patriots
6. Albert Haynesworth Doesn’t Last Long With Patriots
7. Duane Starks Doesn’t Fill Void In Secondary
8. Not Getting Nearly Enough Back For Jimmy Garoppolo
Disagree with the last one. There weren't any tangible reports out there other than speculation from the Browns beat writer that the Patriots were offered a first rounder for JG and I have a really hard time believing any team would want to give up a first rounder for a guy who played not even 6 quarters of meaningful football before injury.
Hard to argue against the rest of them. I'd actually put the Deion Branch trade in 06 near the top. Surprised they missed that one. It was effectively a trade for Brandon Meriweather. The outcome of that trade was Patriots had no receivers in 2006 and still got to the AFC Championship game so it's easy to imagine they would have beaten Fivehead and then the Bears in the SB if Branch stayed.
I didn't really like the Cooks trade that much. It was effectively a trade for Isaiah Wynn and the Patriots haven't had any deep threat receiver like Cooks since we traded him away.