I was really struck by this Sylvester Stallone divorce situation for a number of reasons. The first being that Stallone has been a big influence on me and on masculine culture in broader America for a long time. He’s served to highlight some virtues such as tenacity, commitment, grit, and lots of sports psychology such as a winner’s mindset.

This divorce is not a surprise but you hate to see it. The rumblings were about, Jennifer Flavin released a photo of her with her daughters, it was revealed that Sly had his tattoo of Jennifer covered up, and then came the divorce filing in Florida court. In the filing, Jennifer says that Sly has been deliberately withholding marital assets, thereby adversely affecting her expected quality of living. She contends that he has been doing this in anticipation of being divorced. It is interesting to note that marital infidelity was not mentioned in the divorce filing and judging by social media, there is zero indication that Sly has been involved with another woman. He does have a history of cheating on Jennifer, when they were still dating, and he did famously break up with her through a FedEx telegram back in the 1990’s.

I do not know the full, behind the scenes details of who said what when. All I can do is judge by the court filings and social media. I’ll paint in broad strokes. That said, I see a couple of things that trouble me worth mentioning to my audience.


The closing-ranks photo of Jennifer with her daughters gives one a lot of insight into the situation. When you glance at their vapid Instagram pages, you see unending selfies and glamor shots meant to highlight their sexual market value. They’re fishing for rich men, each of them. Only one of the three has a recent picture with either of the parents and it’s the mother who’s featured. Obviously, it’s the mother heading up the shot across the bow at the father – given the group photo is on her Instagram. None of the daughters are so loyal to their father that they’ve succeeded in dissuading the mother from keeping the photo up, as it unnecessarily raises tensions. You get the sense that Sylvester is broken down enough that this level of female contempt and insolence was a strong dynamic, so strong that it burst to the surface as one of Jennifer’s final acts in the marriage. She went to each of the daughters, or as a group, and secured their fealty. The trust in the marriage has to be pretty far broken for this kind of positioning to happen. It means negotiation between the spouses has completely broken down, the walls have come up, and the war is on.

Such a move on the woman’s part is completely inappropriate and abusive to the man. The sisters are signaling that they buy into the mother’s version of things: something along the lines of Sly deliberately withholding resources and that he’s being a child over wanting this Rottweiler dog at mother’s expense.
I believe this to be the case because the daughters are clearly living hedonist, consumerist lifestyles and are not rooted in their father’s love. For the youngest, who seems really out there, I’d be surprised if she’s more than just dimly aware of a divorce going on. Wealth, in this sense, has become a guard against intimacy. There’s this famous connection that Sly had with the struggle and suffering of his life before he “made it”. He would track down directors on the street and act for them, on the spot. He sold his dog Butkus to make ends meet while he was shopping out his script. He sold the script and immediately went and bought back his dog. Now it appears he’s lost touch. All his success never bought back for him that primal connection to his life’s struggle that he once possessed. It was all roses and red carpets after Rocky.

The man who was an inspiration for so many hundreds of millions of other men ended up having a talented son who died young of a heart problem and had a severely mentally disabled son. At the peak of his high life, Sly married Jennifer, a woman 25 years his junior, and she turned out nothing but daughters for him. You get what you get, of course, but Sly was particularly primed for being a girl dad leading to his downfall. When you build up that much of an empire and you only have daughters to pass it on to, you can’t get away with being an absent father. You will only drive your daughters to your wife, in your absence, and then the lack of intimacy will lead to them scheming to part you from a significant chunk of your wealth. No amount of money can ever make up for an empty childhood, but tell that to pretty young girls who live several-thousand-dollar-a-day lifestyles. Tell that to a woman who modeled for Elite until she met a rich man. The lady never had to develop her maturity.

Jennifer has “secured” for her daughters their lifestyles in perpetuity. She has given them limitlessness and all it cost was divorcing a much older man who once cheated on her. Without love, these are the transactional considerations our closest relationships are reduced to.

Sly, for his part, is most certainly on the ropes. There are no more good scripts being greenlit. Everything is Millennial bullshit for the streaming services. American testosterone drops by literally 1% a year. Bruce Willis is out to pasture. Schwarzenegger destroyed himself. Mel is in the bush leagues. The action hero has come and gone and the man who believed in it the most has been downed by the divorce courts. She’ll keep the beach house. Sly will keep punching but fame was a cruel mistress and exacted her toll: three daughters.