#131. Bill Belichick and You

What the Heel is going on?

May 12, 2025

Hi everyone,

First of all, a happy belated Mom Christmas to all the mothers out there. And a hearty “hey, at least that’s over” to people who have a tough relationship with Mother’s Day. I got to talk to my own mom on the phone yesterday (BRAG!) and then as a gift to my mother-in-law, Maris and I rented a car and drove Maggie the Pug down to New Jersey to meet her maternal grandparents. Although if you’re the people from the rental car place who told me “no pets” while I was lightly hungover on Saturday morning…no we didn’t.

I published a whole bunch of freelance work this week, almost all about basketball, which was kind of a funny set of circumstances. It’s been a while since I’ve done much freelance work on the internet, and I was a little nervous to put so much writing out into the world. I was especially antsy because (and I don’t know if you’ve noticed this) people tend to have strong opinions about sports, and they (I’m breaking new ground here I’m sure) do not always read past the headline before commenting. I am so grateful for all the people who read this newsletter and let me jettison thoughts out of my head and into the universe without putting them into the eyeballs of too many random jerks!

Fortunately, things went pretty well (aside from a few scattered jerks)! Here’s a longwinded rundown, in case you missed any or all of this stuff. (Not unlikely!)

Shout out to my friend (and brilliant editor) Ashtyn Butuso who asked me to write a little something about Boston Celtics coach Joe Mazzulla for the OffBall newsletter. I came up with some advice that imitated Mazzulla’s famously intense press conference quotes. I also wrote a piece for the basketball print magazine (

Flagrant Mag

) that Ashtyn co-founded, and that’s out this week too. Sadly because I live thousands of miles from where the magazine is printed, I don’t have my copy yet. I can’t wait to get it in my hands assuming the USPS isn’t defunded while it’s out for delivery. I love every issue of Flagrant and am over the moon to have gotten to write about three-pointers for the new issue. Flagrant finally offered a way to subscribe, and I recommend if you like NBA or the WNBA (or both) that you do so!

Ashtyn and her co-founder Alex (who both make me laugh so much!!!) also had me on the Flagrant podcast last week, where we talked a bunch about basketball as well as a vast assortment of other subjects such as whether Mrs. Met is (in Alex’s words) “caked up.” I maintain she (Mrs. Met) has a pretty big butt for a baseball, but not on the overall spectrum of butts. Here’s a little video clip from our episode!

flagrantmag

A post shared by @flagrantmag

Another friend and brilliant editor Gaby Paiella asked me to write for GQ about the feeling of being a Celtics fan living in New York City as the C’s fell down 0-2 to the Knicks in the Eastern Conference Semifinals. (The Celtics have since won a game in the series, lowering my blood pressure by 50% in the process.) I appreciated the opportunity to say a lot of backhanded and petty things about my friends and colleagues who cheer for the New York Knickerbockers. I finished my first draft faster than I’d ever written anything, and I’m really delighted by how it turned out. The experience also offered a catharsis that group texts with other Celtics fans did not afford me. AND, I love the artwork they created for the piece!

MS Paint style drawings of a bunch of Knicks fans and one lone Celtics fan, who looks dismayed from GQ's website. — See? Isn’t this fun?

Finally, I wrote a little essay about the Miami Heat for

Katie Heindl

’s newsletter Basketball Feelings. Katie is such a thoughtful and entertaining writer. I’ve learned so much about how to talk about sports with humanity and creativity from reading her work. She’s just the best, and I was delighted/intimidated to do a little writing for her.

If you are not sick of me yet, here’s my performance from last weekend’s 54/54/54 show at 54 Below. I do not have a great singing voice, but I had a wonderful time performing (part of) a They Might Be Giants song for a group of musical theater fans who kept asking me: “What show was that from?”

PEP TALK FOR BILL BELICHICK

Fun fact! That jacket is made from repurposed red flags! (Credit: Kevin Mazur/Getty)

Over the weekend, 24-year-old Jordon Hudson finished third in the Miss Maine competition, which is not the kind of thing you’d normally hear about at all, except that Hudson is in a romantic relationship with 73-year-old UNC football coach Bill Belichick. And look, I believe that love can take all kinds of different forms. Honestly, I tip my hat to Belichick for defying the stereotype of an older man dating a woman half his age by going out and dating a woman who is one third of his age. But there are some weird details at play here. Wait, scratch that. There are only weird details in this story.

During a recent television interview Belicheck was doing to promote his new book, which I believe is called Tales From The Hoodie although I may have made that up entirely, Hudson shut down a question about how the couple met. (You know, the most obvious question to ask any two people when you find out they are dating.) Pablo Torre and Katie Nolan hypothesized on a recent podcast that the topic may be uncomfortable because it seems as if Hudson was only nineteen years old when the pair first met. I don’t think that counts as grooming, but it certainly sounds like…primping to me.

For context: When they first encountered one another, Jordon Hudson had been alive for one fewer year than Bill Belichick had been Tom Brady’s head coach in the NFL. The story actually is that they met on an airplane, and if I was seated next to a 19-year-old woman on an airplane, here’s what I, a 40-year-old man would say to her.

Me: “It’s okay to wake me up if I’m snoring and it bothers you.”
Her: “Okay, old man.”

But who is (potentially) sex-criming whom? Is it weirder for an old guy to date a way way way way younger woman, or for that woman to install herself as a de facto agent and publicist in her way way way way older boyfriend’s career? (Honestly, both the “boy” and the “friend” in the word “boyfriend” seem inaccurate here. He’s more like a “makeoutgrandpa.”)

So to you, Bill Belichick, I want to offer some words of encouragement. First of all, if you two are legitimately happy together, and there’s a legal mechanism in place for protecting you if she tries to write your way-older-than-her children out of your will, and to compensate her for having to see your balls, god bless. If that’s the case, wow. I’m so glad a college cheerleader was able to find the love of her life who happened to be a guy with the disposition you’d imagine the human father of The Thing from The Fantastic Four having.

If this relationship doesn’t work out though, that’s okay too. There are plenty of other fish in the sea. And many of those fish are of an age where you can publicly admit when and how you met them.

(For more substantial coverage of this ongoing story, follow

Madeline Hill

’s newsletter Impersonal Foul or her podcast—The Sports Gossip Show—with

Charlotte Wilder

PEP TALK FOR A READER

I’ve made a couple of little tweaks to this request but nothing ridiculous.

Hi, Josh. I’m losing my house this month. I tried very hard to keep it, but my ex-husband and his lawyer have spent the last 11 months intentionally delaying and obstructing my settlement from the divorce so now I have no choice but to sell. I have no idea where we’re going to find to rent…but wherever we do will have a higher monthly payment than my current mortgage and will put my poor daughter through even more upheaval than she’s already suffered. I am devastated.
- There Goes The Neighborhood

For pretty obvious reasons, I don’t have a ton of upbeat things to day about losing your home. There’s not even really a cliché for this. There’s that saying about how god never closes a door without opening a window, but in this context that sounds like permission to commit divinely-aided breaking and entering. We’re talking about literal doors and windows, here, and for legal reasons I can’t recommend that you try to pry them open.

I also don’t believe that things need to be really bad sometimes for you to appreciate the happier periods in your life. It seems unlikely that as much as you are accustomed to your home’s specifics, you haven’t been taking the concepts of having a roof and walls for granted. So this doesn’t seem like a situation that’s going to be rich with the learning of hard but necessary lessons, or important perspectives you hadn’t considered before.

So many people in America are so close to finding themselves unhoused, and our culture is so unkind to them. Some places have a social safety net. Here’s it’s more like just…a net. Gotcha! You’re stuck here now! This is a terrible reality, and it’s important to acknowledge, but I don’t imagine a ton of character-building comes from experiencing it firsthand. You’re not some Ebenezer Scrooge-type of miser who needs to be reminded that other people exist.

The only flicker of optimism that I can see here is that someday this period will be in the past. That’s not true of all misfortunes, but it seems fair to surmise here. It sounds like you’re in a position to find a new place to live, even if it’s a downgrade from your current situation. On top of that, it sounds like an enormous psychic improvement to not be fighting over a house anymore, even if this new state of being is brought about by losing the house. (It’s the inverse in many ways of how a wedding is a wonderful celebration, but one of the things about having one is that it means you’re done with wedding planning.) Once this dispute is over, you’ll know what you need to do to make your life as hospitable as possible under new conditions.

And, with regards to your daughter, I completely understand your impulse to protect her from further upheaval. But all you can do is provide the best life you can for her, full of the most love and support. Plenty of kids who have experienced turbulence at a young age have happy and healthy future. And plenty of absolute ghouls grow up in two-parent homes with massive square footage. This might not have been your happiest Mother’s Day, but there will be better ones ahead!

PICK-ME-UP SONG OF THE WEEK:
Maura Weaver - “Goner”

My buddy Tommy McNamara came with me to see Chris Farren and Oceanator last Wednesday, and we arrived early enough to see opening act Maura Weaver. We walked into the showroom from the outdoor patio when we heard the opening chords of Maura’s set. Immediately we looked at each other and affirmed what we were both thinking: “This rules.”

Weaver’s 2023 album is very good, but live, there’s even more muscle and groove to the songs. The show was end-to-end one of the best concerts I’ve seen in a long time. The tour is still going on! See them if you can! I ran into Tommy again on Friday night for our friend Anthony DeVito’s standup special recording (which was great) and our conversation returned to Maura Weaver’s excellent opening set. It was a real unexpected treat.

Okay also though there’s been so much good music lately! The new Adult Mom record rules. The HORNS on this one. (I am, as always, a sucker for horns!!!)

And Um, Jennifer?’s album Um Comma Jennifer Question Mark is so specific and fun and full of songs about things I’d never heard songs about before. It’s great! I’ve just heard a bunch of great new stuff this week and I’m feeling hyped about it.