Former New England Patriots head coach Bill Belichick was the architect of a football dynasty that spanned nearly two decades. He returned to Foxboro in 2000 and was given near total control of the team as a de facto general manager.
That same year, Belichick made a draft choice that would forever shape his and the franchise’s fate. He chose quarterback Tom Brady in the sixth round with a compensatory pick. Brady hadn’t performed well at the NFL Scouting Combine and wasn’t taken very seriously by most draft analysts. Belichick said he saw something in him and felt he had the potential to develop into a strong player.
Boy, was he right. He and Brady would win six Super Bowls together over their 20 seasons in New England. Brady is widely considered the best draft pick of all time. For decades, the other 31 teams that passed him up over and over have regretted it. Belichick admits that while he struck gold with Brady, there’s another elite quarterback he feels he missed out on: Lamar Jackson.

In His New Book, Bill Belichick Shares How He Dropped the Ball in the 2018 NFL Draft
Belichick recently released a book titled “The Art of Winning: Lessons from My Life in Football.” The usually reserved, stoic coach opens up in the book about the lessons he learned during his nearly 50 years as a coach.
The Boston Globe cautioned in their review that the book is not a “tell-all” but rather a “paean to his favorite players, coaches, and mentors.”
However, one shocking confession caught some off guard. In the book, Belichick admitted that not drafting quarterback Lamar Jackson in 2018 was a huge mistake. Instead, Belichick chose running back Sony Michel with the 31st overall pick. The Baltimore Ravens traded up with the Philadelphia Eagles and selected Jackson 32nd.
Wild: Former Patriots HC Bill Belichick admitted that not drafting QB Lamar Jackson in 2018 was a big mistake:
Belichick selected RB Sony Michel at 31, and the Ravens traded up with the Eagles to take Jackson at 32.
Imagine if Lamar went to the Patriots 😱
(via… pic.twitter.com/01ajWnaXUw
— Dov Kleiman (@NFL_DovKleiman) April 11, 2025
If the Patriots had chosen Jackson, it could have created continued success for Belichick. Brady decided to leave New England after the 2020 season ended, partly due to a breakdown in the relationship with Belichick. He also hoped for a long-term extension, which the Patriots weren’t interested in.
Instead, the Patriots signed veteran free agent Cam Newton. They struggled all season, finishing with a record of 7-9 and missing the playoffs for the first time since Belichick and Brady’s inaugural season.
In 2021, they drafted quarterback Mac Jones with the 15th overall selection. While they improved that season, they never regained the footing they lost after Brady moved on. After the 2023 season, Belichick and the Patriots chose to part ways. He now coaches for the University of North Carolina.
Jackson has flourished with the Ravens. Although they have yet to win a Super Bowl together, they continue to get closer. Jackson has been named the league’s MVP twice, is a three-time First-Team All-Pro, and is a four-time Pro Bowler.
Michel won a Super Bowl in his first season with the Patriots, scoring the only touchdown in that game. He only played for five seasons with four different teams. Before his sudden retirement in 2023, he won a second Super Bowl with the Los Angeles Rams.
There are many what-if situations in the NFL, but imagining a partnership between Belichick and Jackson is especially interesting.