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When asked at Fanatics Fest in New York to describe the best move he has made in his 30 years of owning the New England Patriots, Robert Kraft quickly identified the time in 1999 when he traded a first-round pick for the right to hire Bill Belichick from the New York Jets. He also acknowledged that making such a bold move for Belichick was a "big risk," given that Belichick previously had a losing record as the coach of the Cleveland Browns. 

According to Belichick, however, it was he that took the "big risk" in accepting the job. The Patriots had stagnated under former coach Pete Carroll and frivolous spending put them beyond the salary cap, limiting what Belichick could do in terms of roster management. 

"As I told Robert multiple times through the years, I took a big risk by taking the New England Patriots head coaching job," Belichick told ESPN. "I already had an opportunity to be the Head Coach of the New York Jets, but the ownership situation was unstable."  

Regardless of who actually took the "big risk," the move worked out well for both sides. After posting a 5-11 record in 2000 -- his first year with the franchise -- Belichick guided New England to victory in Super Bowl XXXVI. That was the first of six Super Bowls for the Patriots under Belichick, kick-starting arguably the greatest football dynasty the NFL has ever seen. He didn't have a single losing record from 2001-2020, and New England made the postseason every year from 2009-2019. 

Belichick and the Patriots mutually agreed to part ways in January 2024. In December of that same year, the 73-year-old Belichick was hired to fill the coaching vacancy at North Carolina, marking his first stint as a college football coach.