6 Super Bowl questions with Ian O’Connor, author of the latest in-depth Bill Belichick book

"I think win or lose Sunday, this is one of the best coaching jobs Belichick has ever done."

Bill Belichick Ian O'Connor book
Bill Belichick speaks with the media during a news conference on Wednesday, Jan. 30, 2019, ahead of Super Bowl LIII. –AP Photo/Matt Rourke

The Patriots’ return to the Super Bowl – the team’s fourth appearance in five years – proved to be a difficult road. New England overcame a series of midseason issues, and had to go through Kansas City to win the AFC Championship.

Once again led by Bill Belichick, the Patriots did their jobs. The New England coach, who has won a total of seven Super Bowl rings in his lengthy NFL career, produced one of his best performances.

Belichick was the subject of a book released in the fall written by ESPN’s Ian O’Connor. Titled, “Belichick: The Making of the Greatest Football Coach of All Time,” the book became a New York Times bestseller.


O’Connor recently answered a few questions about the subject of his book now that a few months have passed since it was published and Belichick is preparing the Patriots to play in yet another Super Bowl.

This interview has been lightly edited and condensed for length and clarity.

What’s been your reaction to the latest Patriots Super Bowl run? Were you worried at midseason that your book might be timed with the end of the dynasty?

Ian O’Connor: For much of the season I thought the Patriots seemed like an older, slower, less impressive version of their former selves, especially on the road. On the other hand, after their back-to-back losses at Miami and Pittsburgh, I wrote an ESPN column saying it would be a mistake to bury them. You knew they would beat the Bills and Jets at home to go 11-5, and I figured Houston might lose at Philly to give the Patriots the 2 seed and the much-needed bye. It played out that way, and I thought they got a bit of a break in seeing the Chargers instead of the Ravens.

Kansas City was going to face pressure to hold serve at home, and by the AFC title game the Patriots were on a roll. Someone still needs to explain to me how Andy Reid could open the game by giving the greatest quarterback ever the ball.


I wasn’t worried about the impact on my book – it was going to sell how it was going to sell. But I admit I was glad that my final words in a 213,000-word book, on page 455, about Belichick deserving the benefit of the doubt that he could fix last year’s problems and return to the Super Bowl, ending up ringing true.

As the current season has played out, what would you add from this year as a coda on the end of the book? Anything in particular?

IO: I will likely add something on this season for the paperback version due out next September, and I certainly think Super Bowl LIII’s result could shape what that something turns out to be. I’ve gotten so many Brady-Belichick relationship questions since the hardcover’s release, and since to many observers Brady has seemed happier this year, that feels like an area that needs updating. I think win or lose Sunday, this is one of the best coaching jobs Belichick has ever done. If they do win, maybe it jumps ahead of his finest coaching job to date — the 2001 season. I’d certainly want to explore that.

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The cover of Ian O'Connor's book about Bill Belichick.
Have you heard from Belichick or the Patriots organization (or former Belichick players) about the book since it’s been published?

IO: I have not heard from Belichick. I have heard from people who know him well, including former players, that they thought it was a very fair portrayal of him, and that was important to me – that it was seen as fair above everything else. Before I covered my first post-book game in Foxborough, I contacted Patriots PR chief Stacey James and said I’d be more than willing to come up a couple days early in case Bill or anyone in the organization wanted to raise any issues with me about material in the book. Face to face. I was told by Stacey that it wasn’t necessary, that he wasn’t aware of any significant issues that Bill or others in the organization had with the book. That doesn’t mean that Bill liked it, or that he even read it. I just took it to mean that whatever he knew about the book, he didn’t feel the need to sit down with me to discuss it.


Do any Patriots fans give you a hard time for your take about Belichick in 2000? And have those opinions changed at all since you wrote a book about Belichick?

IO: Just about every January, either on the anniversary of Belichick’s hiring or during another postseason run, that Dewey Defeats Truman-esque headline gets tweeted out and the floodgates reopen. There’s no point revisiting why that was not considered a wildly unpopular opinion or hot take after he walked out on the Jets, or how it reminds of the things said and written in Indy after Josh McDaniels walked out on the Colts. If you effectively make your living as a critic, it’s good for the soul to feel the sting of criticism yourself. I swung and missed on the greatest football coach ever, so I deserve the annual reminders. I’ve heard from fans who say, “Hey, at least you tried to make up for it by doing this book.” I’ve heard from others who say, “You’re the last guy in the world who should have written it.” And both groups have a point.

Given his fully formed public reputation, what did you find in your research that most surprised you about Belichick?

IO: The divide between Workplace Bill and Human Bill turned out to be bigger than I expected. It’s a Jekyll and Hyde thing. I have a lot of anecdotes in the book revolving around kind and decent gestures, things Belichick has no interest in sharing for public consumption. I needed those anecdotes to meet my objective — to paint a defining portrait of the man, not just the coach.

How much longer do you think Belichick will coach the Patriots? Do you think there’s a chance he ends up coaching another team before his career is over?

IO: Belichick is a young 66, and I wouldn’t be surprised at all if he’s coaching past his 70th birthday. (I can see Brady playing beyond his 45th birthday, by the way.) It’s probably fantasy football, maybe a one or two percent chance, but I think the only other NFL job he’d ever consider is head coach of the New York Giants, the franchise that told him (via George Young) long ago that he wasn’t good enough for the job. But it’s a near certainty that he’ll retire a Patriot, as he should. And what a nightmare for the Jets, Bills, and Dolphins, huh? Imagine being those franchises right now while staring down the possibility that Belichick and Brady aren’t really that close to the finish line.