The Billionaire Midlife Crisis? Philanthropy, Plastic Surgery, Palatial Marriages

Jeff, MacKenzie, and Lauren - and some thoughts on the things we do to stay or look young

I saw her today at the reception
A glass of wine in her hand
I knew she was gonna meet her connection
At her feet was her footloose man

You can't always get what you want
You can't always get what you want
You can't always get what you want
But if you try sometimes, well, you might find
You get what you need
- You Can’t Always Get What You Want, The Rolling Stones

I’m going to wager that you probably know who Jeff Bezos is.

Regular Dude Jeff Bezos driving his 1997 Honda Accord (as pictured here, Jeff is also roughly a decabillionaire)

I will be the first to say my relationship here is … dated. But back in 2003, Jeff Bezos was decidedly more … grounded. (Not on the literal sense, he had a very nice private jet - the Dassault Falcon 900EX.) But that particular indulgence aside, he made a point of staying customer-focused. He drove his 1997 Honda Accord, and said “it’s a perfectly good car” when interviewed on 60 Minutes (as pictured above). And he didn’t go out of his way to look as flashy or live as large as he would later. Here is Jeff and MacKenzie in 2003.

And 15 years later the image of Jacked Jeff Bezos was absolutely a meme.

At this point, Jeff was on top of the world. He was literally the wealthiest man in the world - Amazon’s stock had ratcheted higher over the years as the e-commerce empire had grown and AWS had started to hit maturity, Blue Origin was showing promise and it looked like he was going to actually go to space so he was getting in formidable shape to be astronaut-worthy. Amazon was buying its way into media brands: opening studios; buying the swank grocery store chain Whole Foods and scaring the pants off up the traditional retail space who feared Whole Foods and Amazon coming in from the high end of the spectrum the same way Walmart came in from the low end of the market segment; Amazon Web Services was proving to be an enormous success in cloud computing when all the firms you’d expect to dominate - Microsoft, Google, etc. - were busily dropping the ball.

If you’ve ever read any story of the mighty, you probably expect “but then, hubris was his downfall” to be the next part. Which… maybe.

Jeff’s marked development of physique, at his age, said to most observers not just that he had a good personal trainer but also that he was probably on what’s generally referred to by the shorthand of TRT - testosterone replacement therapy - a certain amount of exogenous androgenic testosterone dosage to bring your levels back up to what you would ideally have at a younger point in life, for anabolic, androgenic, and anti-aging purposes. All sounds fairly ideal, right? And there’s no doubt Bezos had absolutely the best doctors available to guide him in whatever he needed here, so it’s not like he’s just got some steroid-monger quack trying to juice him up into Giga-Chad. But for all that being said, a fairly serious caveat to anyone considering this sort of thing. Suddenly having the testosterone levels of a teenager again, especially when you have the resources of a centibillionaire, can definitely warp your perceptions. Be extraordinarily careful about doing this sort of thing if you are married (and one presumes, monogamous) and especially if your wife is by that point menopausal (or even periomenopausal) because she may really not be entirely enthused about you suddenly having teenage sex drive once again. (I would tend to suspect it probably works better in an open discussion where you both decide to go on hormone replacement therapy to some sort of matching levels of enthusiasm, but that’s a theory on my part; I have only anecdotal data to back it up.) In any case, that may not have been exactly what happened - I wasn’t there - but that’s a bit what it looks like from the outside looking in at the situation.

I suspect you would make any short king jokes at your own peril but it’s your funeral - if you’re curious, he and Mark Zuckerberg are both 5’7”

And so, the starring ladies of our story:

MacKenzie Scott (who was, of course, MacKenzie Bezos when I knew her)

I believe this is her author photo, and perhaps what she might have chosen to be remembered as in less tumultuous times. But of course, as the song goes, you can’t always get what you want.

This is one of the relatively current photos she uses these days when putting a face to her philanthropy work - but as has been her general philosophy, she finds groups she believes in and gives them money to put to work, rather than trying to involve herself or be more of a director for it.

MacKenzie Scott Tuttle was originally from San Francisco, born there in 1970, and had a talent for writing from very young - anecdotally, she had a 142 page manuscript called The Book Worm at age 6 which was destroyed in a flood. But she’d always thought of herself as an author, and when her family had a financially bumpy time she decided she’d make a career path that would either lead her there or permit her to do that also.

MacKenzie graduated from Princeton University - in 1992 - with an English degree in creative writing. She moved to New York City and joined the hedge fund D.E. Shaw, where Jeff Bezos was was the first person who interviewed her. Clearly, it went well.

“My office was next door to his, and all day long I listened to that fabulous laugh,” she told Vogue in 2013. “How could you not fall in love with that laugh?”

The pair were engaged within three months after their first date, and married within six, according to Vogue. In 1994 they left D.E. Shaw, went west - to Seattle - and set up Amazon; it was a very boutique operation at first and didn’t become the juggernaut we all know today for several more years.

Jeff and MacKenzie have four kids (three sons born natively of whom the younger two are twins, a daughter who is adopted from China) - they’ve done a good job of keeping them out of the limelight, and I’ll not be the one to spoil that. There’s a bit that’s been disclosed about them you can read if you’d like; whatever else I may be aware of, you won’t find it here. It’s rather rare to see pictures of the family; this is one of the ones they have publicly available.

Ms. Scott has kept a rather low profile since the divorce despite the amazing amount of philanthropic donations she’s made. Yield Giving tracks this; as I write this it’s somewhat over 19 billion dollars. They cover a wide variety of organizations - thousands of them, in fact - and are extremely hands-off, rather than trying to be tightly involved as the Gates Foundation or other large charitable organizations might be. It will be interesting to see how this works out; the thought of “spread a thousand flowers and see what blooms” will surely bring some unexpected results.

And of course, as expected, we turn to Lauren Sánchez:

This one famously flew around the internet, but apparently it’s not actually real (the Then picture is sourceable - the Now picture cartoonishly exaggerates some of the tendencies of cosmetic surgery) . One might be forgiven for thinking it might be plausible though, because the lady has had a bit of work done here and there.

Here is a photo from June 22nd, 2025 - as the two of them are on display getting ready for their big wedding.

And more directly, you can look at this shot from her Instagram.

I mean, for a man with all the wealth in the world…

It wasn’t my line, but some people closer to him said “What the hell, Jeff?” (OK, perhaps more than “some”.)

Lauren became a little bit famous as a journalist and as an actor, playing journalists of some sort - you probably saw her in Fight Club (playing a news reporter), or The Day After Tomorrow (playing a newscaster), or the Fantastic Four movies (playing a reporter), or White House Down (playing a reporter), or Babylon Five (playing a newscaster)… you get the idea. Do what you know, I guess, although the phrase used to be “typecasting” - but what the heck, I think there’s a certain slice of Generation X who thought April O’Neil was their ideal girl and I’m sure plenty of girls leaned into that. She’s a helicopter pilot, and has managed to entice Jeff back into the chopper - which must have been difficult, as I recall, he was nearly killed in a helicopter crash in 2003 or so, and swore off helicopters.

Back in 2003, Jeff was scouting land for Blue Origin, and his helicopter (not literally this one, but roughly this model) went down. Everyone aboard survived, though it was clear that it could have gone much worse.

In 2024, Lauren put out a children’s book The Fly Who Flew To Space which is described as “a story about a dyslexic fly named Flynn who doesn't do well in school but is curious about life and accidentally gets stuck in the cockpit of a rocket that heads into space.” It immediately debuted on the NY Times bestseller list (can’t say for sure, but one might imagine she had the best promotion money could buy). As you might guess, it’s allegorical-autobiographical, Lauren struggled a bit in school due to her dyslexia, but was still one of the passengers for the “first all-female flight to space” along with Katy Perry and various other high profile celebs. (Incidentally, how can that be? There was a Soviet female cosmonaut back in 1963 - Valentina Tereshkova - who to the best of my understanding went up solo and at least from what I heard, chatted by radio with Khrushchev from orbit and embarrassed NASA.)

When Jeff and Lauren, err, hit it off, they were both married to other people (and had families) - Lauren was married to Patrick Whitesell, a Hollywood agent and founding partner of the Endeavor talent agency; they had been married since 2005 and they had a son in 2006 and a daughter in 2008. Lauren also previously had a son with former NFL player Tony Gonzalez back in 2001, but from my understanding they hadn't actually been married.

This is Lauren, Patrick, and the kids back in the days when they were together. Though I can’t vouch for this, Hollywood Life says “Jeff used to be his good friend. In fact, Patrick is the one who introduced him to Lauren 10 years before their romance made headlines”

The Hollywood Life article has a bit more about the couple; I don’t know enough about them to say. But William Morris Endeavor - err, these days, Endeavor Group Holdings - is quite the Hollywood talent agency juggernaut, so Patrick is probably still doing ok; he’s since remarried from what I understand.

That being said, as best the reconstruction of the timeline goes: in 2018 Lauren and Jeff had (or, alternately, started) their affair; in January 2019, Jeff and MacKenzie released a joint statement that they would seek a divorce after 25 years together. In February 2019, Bezos published allegations that National Enquirer publisher American Media, Inc. had attempted blackmail and extortion in connection with Bezos's relationship with Sánchez. At the time, Jeff Bezos had accused the tabloid of leaking the news on behalf of the Saudis - and in turn, the Saudi prince Mohammed bin Salman of hacking Bezos's phone via targeted attack through WhatsApp - because Jeff Bezos owned the Washington Post, which had previously employed Jamal Khashoggi. The Post had been reporting determinedly on intelligence assessments that the Saudi crown prince (the same Mohammed bin Salman) ordered the grisly murder of the Saudi dissident — and Post global opinion contributor — Jamal Khashoggi, who was, incidentally, nephew of Adnan Khashoggi (a name you may otherwise remember; if you don’t, stay tuned, I’ll write about him more later).

The Washington Post (and NPR) had been continuing to follow up on that story; NPR goes into the details of how the Saudi prince and king-in-all-but-name apparently hacked Jeff's phone and got access to the private communications between Jeff and Lauren (including some spicy stuff). Brad Stone talks about this in his book Amazon Unbound - though the New York Post disagrees and makes front page news about it, as they tend to do. Though it may be far simpler, since it appears that the salacious texts may have been leaked from Lauren’s phone by her brother Michael Sanchez for a rather healthy $200,000, according to the New York Post. And if you ever heard that the National Enquirer was run by a guy named David Pecker, you probably saw this headline telegraphed a mile away:

Being the classy folks they are, the New York Post announced this scandal with the headline Bezos Exposes Pecker

The Bezos divorce was quick - it was finalized in April. The day after it was finalized, Lauren Sanchez filed for divorce from her husband Patrick Whitesell, which was probably a surprise on par with the sun rising that day. Patrick is co-CEO of Endeavor along with legendary vegan power broker Ari Emanuel (whose brother Rahm Emanuel is the former mayor of Chicago, White House chief of staff to Barack Obama, investment banker, and most recently ambassador to Japan under the Biden administration). Patrick and Lauren were divorced in October; as of May 2023 CNN reported that Jeff and Lauren were engaged.

(And for anyone who has asked “Why is Jeff Bezos politically swinging more towards the center? Is it to kowtow to Trump?” you should also consider the alternate explanation that it’s who he’s spending all his time with: Lauren Sanchez is, primarily, a Fox News anchor and actor; Mackenzie is a San Francisco-raised author. I can’t speak to their political stances, I have no personal knowledge, but one might draw some inference - or at very least, Lauren is more likely to cross the aisle and hear from the conservative side of the house. Historically, Jeff’s inclinations were more libertarian, though how much that has evolved is unclear - it’s been quite some time, and heaven knows my own have changed a bit over the ensuing years as well. I would assess MacKenzie as fairly traditionally idealist progressive Democrat and in a position to actually see to it that this works if anyone can - she probably has a better chance than most anyone else, as long as she doesn’t get bilked by grifter “charities” and that’s always the challenge when you’re giving away money. But if Jeff’s pillow-talk-advisor is centrist-right as opposed to progressive-left, it might explain why his reality-check on things has shifted a bit.)

Jeff and MacKenzie had been previously relatively in lockstep with the Democrats, which I suppose made sense inasmuch as they were the party in power. This photo is from the purchase of the Washington Post, which has historically been a pretty reliably Democrat-coded publication.

Now for those of you who took note of the “then and now” photos of Lauren Sanchez above, I get that Hollywood is all about plastic surgery and keeping the appearance of youth.

Cher doesn’t precisely look young here, but she doesn’t look 77 years old either.For someone who has spent decades on tour, she’s doing pretty good. (Now, this is both a lot of plastic surgery work, a great makeup artist, and a fair bit of airbrushing, but still: you go, girl; this lady is my mom’s age and I’m pretty sure everyone in my mom’s age bracket would murder people to look this good.)

This is Priscilla Presley - no, not her deceased daughter Lisa Marie Presley, but the lady who married Elvis back in the day. You might have seen her back in the 80s in the Naked Gun movies or the Dallas soap opera, or more recently on Dancing With The Stars. Take a guess as to her age? She’s eighty years old. She looks - casually, I’d say, in her forties. (HowOldDoYouLook.com guesses 48, so I’m not too crazy.) Organic foods, spa therapy, clean living, nutritional supplements, antiaging therapies, good genes, but also probably more aesthetic surgeries than we’ll ever know.

Speaking of good genes, though. This is her daughter, Lisa Marie Presley, age 54, very shortly before she died from a heart attack. If you were to airbrush away the platysmal bands (“turkey neck”) - or if she’d had the relatively common procedure to tighten it - this isn’t a woman who looks mid-fifties, amidst abject grief, and suffering a life threatening heart condition.

Madonna, age 68, Met Gala. She looks stern. But not wizened. If I’m to look this good when I’m 68, I’ll probably need some help, too. To be fair, I think I should ask Cher for recommendations.

Now, I know the stereotype is that women “get work done” and men just age like schlubs, but consensus is that Jeff appears to to have gotten somewhat juiced, which is common enough these days, and there’s a pretty common thing guys do in fact have touched up: their hairline. Going bald - unless you want to lean into it entirely like Vin Diesel or The Rock (or, lately, Jeff Bezos) - is generally frowned upon, so it’s either the cue-ball look of Lex Luthor or whatever effort is necessary to give you back a reasonable head of hair.

Often guys got away with a toupee - Sean Connery famously did - but these days that’s pretty passe.

Every time you saw Connery as Bond, he was in a toupee. Also for that matter, he had a fairly unflattering one back in Disney’s Darby O’Gill and the Little People, which I’m sure the very mention of has him rolling in his grave anyway.

To be fair, this just looks like Elon had a bad haircut in the first one; it’s not terribly convincing; but I’ve got another article on Elon coming here in a post or two.

And of course… Joe Biden, throughout the years.

This seems a little bit Portrait of Dorian Gray to make him age backwards so effectively.

Kind of amazing to see how much he regrew forty years later, huh?

And if this plastic surgeon’s analysis is to be believed - it’s a fifteen minute YouTube video, and he’s more of an expert than I’ll ever be - then wow, Joe Biden has sure had a lot of facial work done, in addition to the obvious cosmetic efforts to give him back a proper head of hair.

Barry Manilow is reported to have had a facelift and eyelid surgery - I would say “yes, and it looks good on him.”

Not sure about this one. Vladimir Putin may just have been having a bad camera day. In any case, more recent photos of him haven’t particularly kept all that youthful, so he hasn’t kept on with this if he’s been going the cosmetic surgery route.

’But … this is a photo of him at age 72, in 2025. He looks fairly respectable for age 72, and he’s been through a lot. One presumes he has good physicians, I suspect he has more than a few people trying to do him in.

Hollywood, and increasingly the rest of society, seems to live by the famous aphorism that one should, in the words of James Dean: “Live fast, die young, and leave a beautiful corpse.” Or at least look as if one had. More than anything, stepping back from the lifestyle of constant stressors keeps you from aging quite so fast; a luxury more readily available to billionaires who are willing to delegate than politicians and celebrities who very often can’t bring themselves do to that (or, charitably, where events will not permit it) or for whom their brand is themselves.

Which is one reason that it looks like Obama aged thirty years when it actually took six.

So who knows. Perhaps better to be one of the richest people around than even a head of state; heaven knows their lifestyles are comparable and once you’re retired, the stress levels seem to be less other than the endless paparazzi. As long as you don’t go all Howard Hughes, that might be the one to choose. I suspect, for most of us, the choice isn’t likely to present itself.