Inside Bill Belichick's Relationship With Charles Barkley

New England Patriots coach Bill Belichick might be one of the winningest coaches in the NFL, but he's also garnered a reputation for being hard-hearted. Fox Sports even argues that his take-no-prisoners demeanor has paved his way to greatness. Belichick reportedly views his players as "assets," and this seemed to be the case when NBC Sports reported on a potential feud between Belichick and the Patriots' longtime QB, Tom Brady. Brady won six Super Bowls with the Pats, but ESPN noted that Belichick was unwilling to give the star player the contract extension he was looking for. Furthermore, after Rob Gronkowski left the franchise, fans took Belichick's decision to reissue Gronk's No. 87 jersey as a sign of disrespect. These are just a few ways in which Belichick is seen to be callous; at the very least, he's not afraid to take a stand or go against the grain.

Another great sports mind who's unafraid to speak his mind? Charles Barkley. In a 2020 interview with Cigar Aficionado, the NBA superstar discussed his outspoken nature. "It doesn't matter what you say — half the people are going to like it and half the people are going to dislike it," he told the outlet. "You got to realize when you're being honest with yourself, some people aren't going to like that." Beyond their willingness to speak out when they have something to say, Barkley and Belichick have more in common than you might think. Could that be one reason why they're friends?

Charles Barkley and Bill Belichick's relationship dates back to the 1990s. During a 2021 appearance on "Brother From Another," Barkley explained that he first met Belichick three decades prior, when he was coaching the Cleveland Browns. After learning that Belichick was a fan of his, Barkley agreed to have dinner together. "We had a great time at dinner, and we stayed in touch all these years," the former NBA power forward said. "I go up to Foxborough ... every chance I get to go to a game. ... Coach Belichick has been a great man and friend."

It looks like the admiration is mutual. At a 2019 press conference, Belichick ignored a jab toward Barkley, instead taking the opportunity to praise his friend (via Patriots Wire). Joking that Barkley would have made a "great tight end," Belichick added, "[Barkley] is one of the most impressive people I've ever met." That says a lot, coming from someone who coached Tom Brady for 20 seasons.

As a rule, it looks like Belichick and Barkley often gush about each other. On an episode of "Jimmy Kimmel Live!," Barkley seemed keen to dispel public perception that Belichick is a dour, humorless man. "He's really a great guy," Barkley argued. "He's funny when you're around him and get to know him." "Funny" isn't an adjective most people use to describe the eight-time Super Bowl winner, but maybe it's something only a true friend would know.

Bill Belichick isn't the only Patriot for whom Charles Barkley holds a soft spot. Just as Barkley admitted he views Belichick as the OG "GOAT" (via "Brother From Another"), he also feels Tom Brady is the greatest athlete. Thanks to his incredible work ethic, Brady even inspired the NBA player to improve his golf game. "The last Match that I televised with you guys ... [Brady] hit balls for like 10 hours straight," Barkley told Bleacher Report, speaking of a charity golf match. "He got up Sunday morning and played 18 holes before The Match, and when I got to the course, he was in the parking lot running wind sprints." This tracks with TB12's well-documented work ethic, which he's credited as essential to the longevity of his career, per People.

Just as Brady's cannon of an arm is a talking point, so too are his model-good looks. Even Barkley wasn't immune to his charms, when he met the record-breaking quarterback at a training session. "I made a mistake. I looked Tom Brady in the eyes," he revealed on an episode of "Jimmy Kimmel Live!" "I look him in the eyes, and I said, 'Damn, you a pretty man.'" Barkley then joked that he suspects Brady of "mesmerizing" his opponents on the turf. Whether or not that's true, Barkley's bond with both Brady and Belichick proves his continued influence in the sports arena, even though he's left the court behind.