Bill Belichick’s 50-year coaching journey is full of lessons, wisdom, and unmatched football insight. While he rarely sought the spotlight, his words and principles resonated deeply with his players. Now, in his new book, The Art of Winning, Belichick gives fans, coaches, and aspiring leaders a rare glimpse into his philosophy.
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Naturally, Tom Brady—arguably his greatest success story—makes an appearance. Fittingly, Belichick devotes page 199 to the seven-time Super Bowl champion, a nod to Brady’s legendary draft number.
That page features one of Belichick’s signature quotes: “You cannot win the game until you keep from losing it.” It’s a mantra he’s repeated often over the years—so have many of his players, including Bailey Zappe, in a press conference last season after a loss to the Jets. But no one embodied it quite like Brady.
Belichick explained the quote in depth during a recent episode of The Pivot Podcast, breaking down how Brady personified it through three fundamental traits.
“As a QB, we all know the worst situation you can be in is long yardage. And so as long as the ball moves forward, you stau out of long yardage. Tom did such a great job of not allowing negative plays to happen to our offense. No pre-snap penalties, no sacks, if the run didn’t look good, he would check it to the other side. But he kept us out of negative plays,” he revealed.
Second, his timing and distribution were elite. Brady consistently got the ball out quickly and accurately, spreading it across his arsenal of weapons. He studied his teammates—understanding their strengths, tendencies, and roles—allowing him to elevate their performances and use the full width of the field.
” Number two, as I’ve told Tom many times, Tom, we can’t gain any yardage until to get rid of the ball. Give the ball to somebody else who can. And he did a great job of that. Tom really understood how Randy could be productive, how Julian can be productive, James White cam be productive. It’s like point guard.”
Third, and perhaps most crucially, was his decision-making. Brady rarely turned the ball over. His vision and field awareness were unmatched, and he excelled in situational football, always seeming to make the right choice at the right time.
“And then, of course, he made great decisions under pressure and had a tremendous ability to see the field understand situational football, and make quick decisions under pressure.”
Bill speaks highly of Tom every time someone mentions him. No wonder he paid tribute to him in his book, though the idea wasn’t his to begin with. We can thank Jordon for that.
Bill paid tribute to Brady in the Art of Winning, but the idea wasn’t his
Given how their relationship unraveled toward the end, when Belichick let the Michigan alum walk away, there was reason to wonder if Brady would feature in the book at all. Robert Kraft, who ultimately fired Belichick, doesn’t appear in The Art of Winning, making Brady’s inclusion even more notable.
Fortunately, the two seem to be on good terms again. Not only does Brady appear in the book, but he’s also given his own tribute chapter. But it wasn’t Belichick’s idea to assign symbolic page numbers to the greats who shaped his coaching career. That credit goes to his girlfriend, Jordon Hudson.
Belichick has referred to Hudson as his “creative muse,” and it’s easy to see why. It was her idea to pay homage to key figures by assigning them pages based on symbolic numbers—like 199 for Brady, or 56 for Lawrence Taylor. The concept instantly resonated with Belichick, and it helped form the structure of the book.
“She had a lot to do with it.One of the great ideas that she came up with was, when I was writing the acknowledgments and kind of tribute to Coach Parcells, Lawrence Taylor, Tom Brady, my dad… she came up with the idea of why don’t you give them their page.”
It’s a fitting way to honor the individuals who helped Belichick turn winning into an art—and to highlight the players who, like Tom Brady, became legends under his watch.
