Is it Okay to be A Gold Digger?

What’s more American than the NFL? Going berserk when someone gets something they don’t “deserve.”

Folks, I had a big birthday last week, which felt by turns wonderful and shocking. I won’t dwell on the latter, but under the former heading, I was delighted to spend the weekend with my extended family and the actual day with beloved friends who made it special for me thanks to an impromptu celebration at a great restaurant. When I was asked what I know now that I didn’t ten years ago, I didn’t hesitate to answer: the quality of my relationships and people in my life is as good as it has ever been: filled with people who listen and show up, who hold themselves accountable, tell the truth and care about the needs of others. I couldn’t always tell the givers from the takers, and now I can. If you’ve ever seen those features where they ask older women for what kept them looking and feeling great into old age, maybe you’re used to replies like “moisturize your neck” or “don’t neglect the backs of your hands when you put on sunscreen,” but this is mine: surround yourself by people with a lot of beauty on the inside.

It's with that bit of advice that I will attempt to segue into this week’s topic. As my contemporaries and I stand firmly in what I used to call “Middle Age” but have now decided I should rechristen as “Dawn of Elderhood,” the relative appeal of one’s outsides over time tends to become as frequent a subject of conversation as it was in our teens and early twenties. The way women of my vintage tend to cope is by contemplating (and even booking) a visit to the plastic surgeon; after a certain point, you accept that needles are no match for the efficacy of the scalpel. This had made us fairly obsessed with scoping which of our contemporaries have “had work,” and why we know the clinical terms for nearly every cosmetic procedure and region of the face. For men, however, the most effective expressway to the restoration of your youth still seems to be far more painless (at least at first): getting a girlfriend who might have been born after you got a driver’s license, registered to vote, or graduated from college. Fellas: date someone who might be old enough to rent a car but is a few years (at least!) from being eligible to run for president and you will have a new lease on life.

Society teems with such examples, and I would say it’s enough of a given that most men who marry late in life or remarry will select younger women that a difference of a decade will not be remarked upon or even noticed, especially if the woman is established in her own right and the man is considered a “catch.” Ryan Reynolds is 11 years older than his wife Blake Lively, while Jay-Z has a dozen years over his spouse Beyoncé; George Clooney married 17 years-younger Amal but they rarely seem to draw any jabs about their age difference (surely it helps that she’s an Oxford-educated human rights lawyer). But even if they did, would it matter? Not only does cresting the hill of 40 help you to stop basing your life decisions on what others think, it’s hard to imagine that any of them would care: by and large, men do as they please and can expect to take minimal shit for it.

And then there’s Bill Belichick.

Even if you knew as little about his record-making coaching legacy as I did and were far enough removed from the hometown of his former team that it would have been difficult for you visually identify the man even in a lineup of two, by now you likely know it all thanks to the fact that since 2023, he has been dating Jordon Hudson, a woman 48 years his junior.

While I am not jumping to hoist “the heart wants what it wants” flag that I more or less waved in defense of the so-called “lavender marriage” of von Furstenberg-Dillers the last time you were here, I’m still figuring out exactly what I think of these two. Of course, it has not been hard to pinpoint just what it is about this relationship that shocks people, or puzzles them. Though I’m no famous man, I too think I could date 10 years older or younger, but make it 15 and I might be out. There’s also the fact that someone 48 years younger than I is currently a baby. So while I am legitimately stumped, it hardly makes me angry as angry as it has made quite a few sports fans.

When I shake out the coverage of this love story, I have been surprised to see how little of it hinges on the indecency or implied power inequality in a relationship between much younger woman and a much older man; in fact, I cannot remember any recent column inches suggesting that someone old enough to have fought in Vietnam might be somehow exploiting someone who just finished school (though the fact that “consensual” and “consenting” are so often used when describing them suggests that many people only grudgingly approve). Is this the magic of feminism? Or a strange by-product of the position that people’s sex lives are their own business? If only.

Don’t they say you should marry your best friend?

Though I haven’t seen too-too many Attaboys (though it seems like that would be reaction of a tok that I’m simply not on), I think the reason any fervent labeling of Mr. Belichick as a “dirty old man” (consider this fact: he married the mother of his three children around the that Ms. Hudson’s own father was born!) has been held back is that almost everything the public doesn’t like about these two as a couple has been blamed on her.

What is absent in the commentary regarding le sex is all lit up around gender: vixen, sugar baby, gold digger and even “elder abuser”: how else could such a woman have so much power over such a man? In Katherine Rosman’s article from the May 20 edition of the New York Times, she quotes former Patriots general manager Upton Bell: “It’s ironic that a man who really controlled everything – and I mean everything – now is being controlled by some other person.”

Given her involvement in his business affairs, it seems clear that Ms. Hudson has no fear of claiming her seat at the table, overseeing things that would generally fall under the purview of manager, publicist or maybe attorney, and for which we may be open to the idea that while she may have interest and even aptitude (already debatable), she is too young to have any real experience. However, as someone who seems to have as much information (read: none) everyone else who has been drawn in by this saga, it’s not immediately clear to me if and how that control is coercive. And that leaves me to wonder if – just as people Ms. Hudson’s age are given to seeing feedback as “abuse” – those of us who have been around longer are confusing “ill-advised” with ill intent.

People do a lot of stupid things in the name of what they understand to be love; it may mean something different to Bill, or Jordon, or both of them than it does to you or me; perhaps it means something different to him at 73 than it did at 23 or even 63, and means something different to her at 25 than it will in the future. But he would not be the first old person to define “love” as Companionship, nor she the first young one to define it as Security (though again, there’s no evidence that they do). Who is to say that Mr. Belichick does not believe in his heart that the commodities he exchanges with Ms. Hudson are not worth the price that they have negotiated, or even that she herself has set? If they are both in the market for the thing the other offers, can their transactions still be morally wrong?

According to the commenters in the referenced article, yes. “The way Ms. Hudson had aggressively manipulated the situation to acquire her own fame, money and power in her own name, out of thin air!” wrote one reader. “I was married for thirty years to a man 39 years older than me…however there was no money or fame or ambition involved – that is what makes this story worrisome,” said another. Interesting, isn’t it, that it’s not her innocence or youth – things you cannot grow, invest or reclaim – that all these strangers are concerned with protecting — it’s his cash.

At the risk of giving away my formula for determining whether we should give people a break or hold them to account, I always try to imagine the contested scenario with different vital statistics, other identities and proper nouns. Life experience does count for a lot, but it’s hard to quantify, and it’s not everything: I recently finished reading Bill Gates’s Source Code; he had come up with most of the programming that would constitute Microsoft’s key products by the age of 19. Since I think I’m plenty smart but would not even compare myself Bill Gates, I also submit that the business of “content creation” has enriched a lot of young and not particularly business-savvy people — a fact surely not lost on Ms. Hudson. In her mind, I am sure there is no reason to think she should be any different, especially with the sudden notoriety that brands are as eager to monetize as the fame-aspirant.

Were it Belichick’s daughter or son – or even granddaughter or grandson – and not she who were trying to get the coach’s merch empire off the ground, would we have as much of a problem with it? And what skills would we really obligate this relative to have before we dimissed them? Scions from Rockefeller to Ford to Walton to — ugh — Trump — have been recruited to grow dynasties forever, and if she indeed plans to become his wife, should she not have at least visibility to the plan? Is there not a version where we applaud a man for handing power over to his wife instead of a board of directors? As for her qualifications, before “Free Britney,” it was extremely rare to see critics or fans question a parent who oversaw the career of their performer child (her father Jamie famously has only a high school education and no entertainment industry experience of his own), and presumably a minor is much more vulnerable to financial and emotional harm than a six-time Super Bowl winner. Were Ms. Hudson the privileged daughter of some captain of industry and not a Maine fisherman, would we be more easily persuaded that she is not merely “in it for the money,” but just more at home with rich and powerful men than most, as well as possessed of some “native” business acumen that qualified her to act as her fiancé’s representative? Were she a product of Harvard and not a hair academy followed by little known state school 35 miles away from its ivy-covered walls, were she a little less of a glamourpuss and he a little more handsome, what might we say then? I don’t make these queries in the pursuit of “Justice for Jordon,” I’m trying to filter out the classism and anti-feminist elements of the backlash before I decide.

Besides, while those anxieties may be nothing new, I believe the most interesting thing to emerge here is the particular strain of age hostility attached to these two. What makes it most galling to the mediasphere is not just that she stands to profit from her involvement in his business enterprises: it’s that she is not as good as she thinks she is. What annoys us is that Ms. Hudson seems to have set sights set on a “main character” status that feels generic and largely unearned, making the true tension of this story is not their generation gap but her own generation: the one they call “Z.” For Ms. Hudson’s antics have not endeared her to people old enough to clearly remember any of his big wins (he clinched his first three Super Bowls before Ms. Hudson entered elementary school), but she is likely a lot better received by the people of her time. And because men – especially single ones with a little or a lot of money – will always have the option and will probably always choose to date younger women, we should not be surprised when the next crop of trophy wives are not merely sexy homewreckers or even sweet faced former exotic dancers like Anna Nicole Smith, but terminally online, girlbossing, get that bag and man in finance viral-obsessed vixens who share everything and appear to feel bad about nothing. Thanks to the constant marketing of social media plus the veneration of wealth that bloomed on the reality shows that shaped their language, their attitudes and penchant for drama, this is how they see the world, and they know as anyone can that someone always needs to found to foot the bill.

Before we paint all Gen Z’s emissaries as shallow monsters, however, consider one last thing: the narrative of the conniving fortune hunter always blots out the fact that the owner of the treasure chest has motives too. Some people are so intelligent, successful, or larger-than-life that it is difficult for them not to dominate all the people around them. But we mustn’t assume that a person who is abundantly gifted or compensated also possesses emotional fortitude. In fact, many powerful people surround themselves with those who depend on them for access. This is why, ahem, some leaders take on unskilled or inexperienced people to run their organizations: when you have limited inner resources, these imbalances are what you may count on to look and feel good. It’s possible that Ms. Hudson is steadily building a tower to lock Mr. Belichick away in, but maybe what we don’t like contemplating is that she demolished one – fully enough, in fact, to reveal that this celebrated leader of modern day gladiators is now jsut a regular guy in career transition and late life. His six rings cannot diminish his regular guy insecurities, so he is currently treating them with the company and maybe even love of a girl who is way out of his league. It seems likely (or at least possible) that Ms. Hudson is no more or less powerful than nearly any pretty girl giving some high-quality attention to a guy past the age of retirement, whether he met her at Starbucks or the strip club. But what makes us see her as a threat is that the one she’s giving it to is the winningest football coach of all time, and it’s working. Why? Not because of any evil sugar baby juju she possesses, but because this man…is a just a man.

Some years ago, I read Empty Mansions, which tells the life story of the copper heiress Huguette Clark, who bought and maintained several blue-chip properties that she never moved into or even visited. Years later, she entered the hospital for skin cancer treatment and decided to stay – and that is where she died 20 years later: she could, so she did. 2017’s The Betancourt Affair details the blockbuster criminal trial charging L’Oréal heiress Liliane Betancourt’s confidant François-Marie Banier with undue influence thanks to over one billion euros in gifts of cash, property, art and life insurance policies she transferred to him near the end of her life. Did this leave her a pauper, you may ask? As the onetime richest woman in the world, the amount she bestowed upon him was less than 5% of her holdings, and still likely more than he could have ever spent, so no: she died unimaginably rich, rich, rich. I mention these two tales because of the question they both pose at the end: if it’s your money, who can say what you do with it or whom you share it, no matter how profligate, foolhardy or icky? As much as we might envy the wealthy as well as wish that they had had wisdom (or taste or esteem or perspective or morals or self-knowledge and self-preservation – the list goes on), we can be grateful for the one thing they are nearly always able to provide, no matter how removed we may be from their munificence: the reminder that good, common sense is so dear that sometimes it is even beyond the grasp of the richest of them all.