Skip to Content
Arts And Culture

Tom Brady: The Leather Years

US former football player Tom Brady walks the runway during the Gucci Cruise 2027 collection fashion show at Times Square in New York on May 16, 2026.
Angela Weiss/AFP

The post-retirement track record for your hyper-competitive, multiple-champion GOAT-class athletes is not necessarily one you'd want for yourself. So often they seem stranded, often surrounded but generally quite alone, peering down from atop a mile-high butte of money and notoriety at a world that is much too far away to recognize; the people moving through and within it, to the extent they are visible at all, have a busy and eminently squashable ant-like aspect. We can probably assume that we look roughly as strange and unreal to them as they do to us.

There is something alien about this type of person that goes beyond their superhuman and highly public accomplishments, and that is true even before wealth and fame shove them further and further into abstraction. That otherness is sort of spiritually hypertrophic, in the way that tennis players tend to have one really strong arm and one comparatively normal one, but mostly just a reflection of how lopsided this sort of lifetime spent in relentless pursuit tends to leave one's being. As any/every sports biography or feature profile can tell you, this is just What It Takes. Everything combustible enough to serve that all-consuming pursuit gets consumed; it becomes fuel, and things that might be necessary later in life are chucked into the furnace in the moment to keep the engine stoked and burning.

The more distance that time puts between these champions and their old glories, the more that deficit tends to come into relief. There's a type of feature story about this, too, and it's common enough to be a sort of genre unto itself. Sometimes the dramatic action is someone who has burned what these people burn wondering where everything went; think of Michael Jordan telling Wright Thompson, in 2013, "I drove myself so much that I'm still living with some of those drives. I'm living with that. I don't know how to get rid of it. I don't know if I could." Sometimes, usually but not always in instances that require writing around an uncooperative subject, that incapacity for insight is the story. Think of Tiger Woods clearing rooms in a Navy SEAL "Kill House" training facility and wrecking his body in an attempt to better understand his domineering and rapacious military father, also in a Wright Thompson story. Steve Kerr, a much more enlightened and insightful being than Jordan or Woods, presents a different version of this protagonist in a much more recent Wright Thompson story, one who is trying to figure out what his existence might be like without the old rhythm of competition and camaraderie, and with nothing but his own very full life to fill it.

There is a reason why Wright Thompson writes so many of these, beyond the basics of supply and demand, his talent, and a certain editorial/cultural bias towards these kinds of stories being both grand in scale and grandiose in tone. In the broad strokes, this is a pretty common trajectory for a champion's afterlife, and one that lends itself to Thompson's heroic scale and register. It is, at some level, always the same story. It's about men who shaped and stunted their beings around the need to command and dominate trying to figure out what to do with themselves when their bodies no longer permit them to do it as they once did.

In the abstract, this is poignant stuff. People have written tragedies about the difference between what you can reach and what you can grasp, and what you can touch and what you can keep, and what that all costs, for as long as people have written about anything; sports deliver enough of this sort of thing that I have written them about a former Mets pitcher who retired with 9.3 Wins Above Replacement and a different Mets pitcher who retired with 15.7 WAR for this website. In a more specific sense, though, these stories are mostly just about swapping new appetites for old ones, and this type of guy continuing to throw important things into the furnace out of habit, or just because our protagonists naturally run cold. Seen from that angle, this story still retains some pathos, but also looks much more obviously pathetic—extraordinary men giving the last full measure to avoid acknowledging the same sad, obvious stuff that they have in common with everyone else; people uniquely positioned to take on any challenge in the world who mostly just get divorced instead.

What pathos there is to find here lies in the fact that while the men in these stories do things traditionally associated with masculine leisure—upscale gun shit, committed campaigns of adultery that play out as a series of escalating heat checks, gambling, sports-adjacent drinking in all-male groups, the catechistic going-over of old slights and beefs, compulsive golfing—they are categorically incapable of doing it in a leisurely way. Jordan, approaching 50, winds up locked in a too-intense game of one-on-one with one of his team's best players that leaves him sore for days. Instead of regular-style narcissistic validation-seeking, Tiger Woods haplessly and inexorably commits himself to becoming The Tiger Woods Of Adultery. These men don't have to work, but they forgot how to do anything else, and long ago lost any other way to treat every day but as another thing to be defeated. There are millions of Americans like this, as it turns out, many of whom have never done even one single cool sports thing in their lives—comfortable people who fundamentally cannot be at ease; people whose lives of unconscionable but undeniable leisure are nevertheless haunted at every turn by their concerns regarding the troubling likes on Zohran Mamdani's wife's social media accounts.

You would not say that Tom Brady isn't in this class, exactly. In the years since he ended his NFL career, Brady has been fantastically busy. He is both an NFL broadcaster and the minority owner of an NFL franchise, but he is also deep into the sort of faddish rich guy things his cohort is into, like podcasts, clothing lines, making stilted half-documentaries about himself, and striking hard-to-parse business partnerships with the Kingdom of Saudi Arabia; he cloned a pet and tied it into a brand deal. Brady is, literally and figuratively, a divorced man, to a sufficiently extreme level that both baseball cards and cosmetic surgery are involved. But one thing that you can say about Tom Brady that cannot readily be said about his peers in the Relentless Pursuit Of Everything (Retired) community is that he would do this and they would not:

US former football player Tom Brady walks the runway during the Gucci Cruise 2027 collection fashion show at Times Square in New York on May 16, 2026.
You know he had to do it to 'em. (Angela Weiss/AFP via Getty Images)

"When the odds are stacked against you, when you’re facing your own 28-to-3 moment—and believe me, it’s coming—you will have a choice to make," Brady said earlier on Saturday, "to quit or to fight your ass off." He was making a commencement speech to undergraduates in Georgetown's McDonough School of Business, shortly after which he got in a helicopter so he could be swaddled into a full leather outfit and walk the runway for Gucci's 2027 Resort Collection. The mood of the show was, in the words of the New York Times, "meta-kitsch." The event was held in Times Square amid screens bearing ads for (currently) nonexistent Gucci-branded water and wellness supplements; a voiceover said things like "dress for the job you want, and the job you have." Brady was one of several participants in the show—Paris Hilton was another—who were there not because they were models but because they were so recognizable. Their presence was supposed to remind you of something, or just of themselves.

As with a lot of high-level fashion stuff, it was clear that there was definitely some irony happening, but less clear what was being satirized, or how. The gambit of dressing the utmost All-American Quarterback—even one who, at this moment, no longer really even looks like someone who Looks Like Tom Brady—in black leather, the fabric of fetish and fascism, is legible as a provocation of some sort or other. The winking idea of the All-American Quarterback as a leather-sheathed figure of domination is right there, but Brady can't quite pull it off; the domination is right there, but the face is somehow too taut and focused to wink. "I believe in manifestation," Gucci designer Demna said before the event, "and I feel like I wanted this show to be about that—what Gucci can become." Times fashion critic Vanessa Friedman approved of Demna's vision, which she described as positioning the brand as "a one-stop shop for the power players of the Manhattan of the mind." She was less impressed with Brady's runway work.

om Brady walks the runway at Guccicore: Gucci Cruise 2027 at Times Square on May 16, 2026 in New York City.
We are the goon squad and we're coming to town. (Taylor Hill/Getty Images)

All of this absolutely makes me feel like I've been kicked in the head by a horse, to be clear. Brady, like everyone else in his rarified cohort of Olympians adrift, is a rare type of warped human being, but also a signifier in his own right. This goes beyond the lacquer and distortion that invariably accompanies becoming a brand, and pushes into further realms of inscrutability—beyond the Manhattan Of The Mind, wherever and whatever that might be, and into the inhospitable cultural dusklands of appetite, accumulation, repetition, and a wrung-dry, ritualistic sort of reinvention.

Brady is a cipher, but he also stands for success, to the point where his presence at a business school graduation or corporate event or on a fashion runway is more or less as a stand-in for the very concept. Success is not a value, though, and the pursuit of it is not a belief system or an especially ennobling or dignified way of being in the world, or really anything but work. This may be why the old heroes seem so lost and so hungry in all those Wright Thompson profiles, or why these photos of Brady seem so uncanny. Send the ghost of some old god sailing down the runway in strange new clothes and you will certainly succeed at creating some kind of provocation, but also only wrapping the same sad American mystery in a new disguise. Maybe that's the gag, or maybe it's just what it looks like.

A referral from a trusted source is the #1 way that people find new things to read. So if you liked this blog, please share it! 

Stay in touch

Sign up for our free newsletter