Tom Brady Reveals Why Watch Collecting Is Such a ‘Rabbit Hole’

Tom Brady is big on watches. Like, really big on watches. “Twenty years ago, I bought my first two watches,” he explains. They were aspirational, signals to himself that he’d arrived as a young pro quarterback. “I always felt like, ‘Man, if I make some money, I’m going to go buy some watches.’ And I went in, I picked out my two favorite ones at the time, and it started me on this journey. I guess it’s a rabbit hole, especially now—this expression of style, and this permanence of time on your wrist, and what it means to you.”

One of of those two original watches, as it happens, was an IWC. Now, a couple of decades on, Brady—not retired, not yet, but keenly aware of where he stands in his career—is waxing philosophical on watches and time as an ambassador for the Swiss luxury brand. It’d been a couple years since Esquire connected with Brady, which happened right after his move to Tampa, so we chatted about how his collection and approach to wearing watches have shifted during the pandemic, why he plays the long game when it comes to style, and what it’s like living in “the golden age of watch collecting.” This conversation has been lightly edited for clarity and length.

Esquire: We last talked with you a couple of years ago. Have there been any additions to your watch collection since then? Are you wearing different things?

Tom Brady: Oh man, I’ve been wearing all my IWCs, obviously, of late. I got a Portugieser, a new one. It’s interesting in football the last couple years. Because of Covid and our travel schedule, we haven’t been required to wear different travel gear, and we haven’t gone out a lot. So, a lot of my watches I’ve been wearing have been more sporty, rather than something that I would wear with a suit. I’ve just been kind of wearing my big pilots. I love the Top Gun obviously, because I just think it’s a really cool name. And I love the movie because that was our era. But the watches are amazing. The new novelties—the Tahoe, the Woodland, the Mojave—are very cool ceramic pieces. You can wear them for everything; they’re very durable.

brady wearing the top gun chronograph in woodland ceramic

Brady wearing the Top Gun Chronograph in Woodland ceramic.


You touched on something that I wanted to ask about, which is just how the pandemic has shifted your priorities, if at all. I’m thinking of watches, of course, but also in life in general.

I moved to Tampa on April 1st, two years ago. And a lot has happened in those two years. It’s crazy when I think about the amount of things that happened personally and professionally, the amazing successes in my professional career. But also…just look at the world in the last two years and what we’ve gone through from the beginning of the pandemic to now. It’s altered all of our views on time, on work. For me, I’ve prioritized the things that I want to spend my time doing. And now I’m at the point where I retired two months ago and then realized, “Oh man, I’m not ready.” You know? But at the same time, I know I don’t have five years of football left, and I’ve got to make the most of it in this moment.

I’m at the point where I retired two months ago and then realized, “Oh man, I’m not ready.”

When you’re faced with something coming to an end, you realize—whether that’s a career choice, whether that’s a moment in time, or whether that’s your life in general—you want to make the most of it. And you think about the people who made your life really special. The people who made your life really joyful, and surrounding myself with people that inspire me, and doing things that kind of bring me closer to what my goals are. Which is to be a great parent, to be the best husband I can be, and to be a great teammate to the organization I’m involved in. And then beyond that to be a great friend, and to work hard. And to show my kids and to be a good example for them of what hard work means, and find something you love to do so you can work hard at it.

It feels like there’s a greater philosophical weight to the idea of permanence right now. With the world feeling so unmoored, finding things that will stick with you for a long time means something more. Buy less, buy better is a cliché at this point, but it seems truer than ever.

You know, I’ve always felt like quality over quantity is most important in my life. And choosing right, not choosing fastest or cheapest. Trying to choose for the long haul, and make permanent decisions as opposed to instant gratification. And I think my career has been built on playing the long game. A lot of that is just recognizing that you’re investing in time, and not investing in an immediacy to a decision that may feel gratifying in the moment, but in the end may take away from what you’re trying to achieve. So, I definitely feel that in my relationship with time, my relationship with style. And fashion has always been an expression of my personality, an expression of my style.

Pilot’s Watch Chronograph Top Gun Edition ‘Lake Tahoe’



Twenty years ago, I bought my first two watches. I bought an IWC that I still have my collection and I bought a Panerai that is not in my collection anymore, at the Tourneau on 57th street in New York. I always felt like, “Man, if I make some money, I’m going to go buy some watches.” And I went in, I picked out my two favorite ones at the time and it started me on this journey. I guess it’s a rabbit hole, especially now—this expression of style, and this permanence of time on your wrist, and what it means to you. And I’ve been very fortunate over the years to work with different watch brands. But working with IWC is really the culmination of that in my life. I love the brand. I love the CEO, Chris; the chairman of Richemont, Johann, has become a great friend of mine.

How much thought do you put into what watch goes with what outfit? Is it very considered, or more of a throw-and-go kind of thing?

I think you can start with your watch or you can end with your watch. That’s the cool part about it. And in this day and age, there’s something for everyone in watches. This is like the golden age of watch collecting. And I think it’s forcing a lot of watch manufacturers to step their game up, too. It’s pretty cool to see what people are coming out with, because people want to appeal to this global audience of watch collectors and watch fans. And I’m certainly one of them. So I want see what people have and what people are doing. That’s really fascinating to see.

brady wearing the top gun chronograph in "lake tahoe" ceramic

Brady wearing the Top Gun Chronograph in “Lake Tahoe” ceramic.


I feel like some people look at back and think, “Oh, if only I’d been able to get into watches way back when…” But we kind of have it all right now.

We have more now than ever. And, I mean, the prices on the secondary market are insane and it’s very difficult to get watches because people are seeing them as collectibles now. People want to kind of buy things for special occasions. In our quarterback room we talk about, “Man, I’m buying so-and-so a watch as a token of appreciation. What can I get all the offensive linemen to show my appreciation that they can keep for a long time?”

I suppose it’s been like that for a while, but now there’s so much awareness about it. People are looking to buy something to celebrate an anniversary, to celebrate a special occasion, to celebrate some moment in your life. And I think it’s a very cool time to be a part of that. And yeah, maybe we missed the last 50 years, but I’ve got to believe the next 50 years are going to be just as amazing, especially to see what time looks like in the future. I think people are finding different ways in this digital age to connect with the future. And I think we’re still at the beginning of that, too.

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