New England Patriots owner Robert Kraft made thousands of good decisions to build a dynasty that won six Super Bowls between 2001 and 2019, but one stands out above them all.
During the “Dudes on Dudes” podcast with former Patriots stars Rob Gronkowski and Julian Edelman, Kraft was asked to name his “best decision” as Patriots owner. The longtime owner picked the one he “got questioned the most” over when the Patriots traded for former head coach Bill Belichick.
“I gave up a No. 1 draft pick for a coach who had only won a little over 40 percent of his games, to get him out,” Kraft explained, “I think getting Bill Belichick to come to the Patriots in 1999 was a big risk, and I got hammered in the Boston media. But he was with us for 24 years, and we did OK.”
Belichick was set to become the New York Jets head coach at the time, but the Patriots traded that pick for Belichick’s rights. It led to Belichick’s rise as one of the greatest coaches of all time amid the six Super Bowl wins and a 266-121 record with the Patriots.
That’s a far cry from his 36-44 record with the Cleveland Browns in the 1990s, which had Patriots fans rightfully skeptical. Belichick, of course, found a player in New England that he never found in Cleveland — former Patriots quarterback Tom Brady.
Bill Belichick Found Tom Brady in Sixth Round
Belichick, who served as the de facto general manager, had the Patriots take Brady in the sixth round for the 2000 draft with the No. 199 pick out of Michigan. Scouts didn’t have Brady on the radar as a future franchise quarterback, and the Patriots were established with former quarterback Drew Bledsoe at the time.
Belichick’s first season with the Patriots didn’t go well as the team went 5-11, which was a drop from the 8-8 season under former head coach Pete Carroll in 1999. The Patriots had a two-year playoff drought and no playoff wins since the 1997 season going into 2001, and Bledsoe went down with a severe injury against the Jets that year.
It ushered in the opportunity for Brady to take over, and he led the team to an 11-5 record and a playoff appearance. Brady then led the Patriots to a snowy Divisional Round win over the then-Oakland Raiders, but Bledsoe took over in the AFC Championship Game against the Pittsburgh Steelers after Brady struggled.
Bill Belichick Going Back to Tom Brady Changed Everything
Belichick then made one of the most pivotal coaching decisions of his career when he went back to Brady for the Super Bowl in a win over the then-St. Louis Rams. Bledsoe left the Patriots after the season, and Brady became the starter, which led to back-to-back Super Bowl wins in the 2003 and 2004 seasons.
Belichick then coached an extra-loaded Patriots squad in 2007 to the only 16-0 season in NFL history, which resulted in a massive Super Bowl upset loss against the New York Giants. While the Giants thwarted the Patriots’ Super Bowl hopes again the 2011 season, Belichick retooled a consistent Super Bowl winner again with Brady amid championships in the 2014, 2016, and 2018 seasons.
While Belichick didn’t enjoy as much success after Brady’s departure to the Tampa Bay Buccaneers in 2020, the longtime coach built an unprecedented two-decade dynasty in Foxborough. Belichick stepped away after the 2023 season, but he returned to the coaching ranks for 2025 in college football at North Carolina.
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