One of the living legends of the Manosphere is Porfirio Rubirosa. His life is chronicled in the biography The Last Playboy: The High Life of Porfirio Rurbirosa, a fascinating review of the legendary Dominican cad. It’s an impressive collection of research by Shawn Levy, author of Rat Pack Confidential. Not only does it cover Rubi’s life in depth, but it reads like a who’s who of 20th-century celebrities. The book is a must read.

Rubirosa (or Rubi, for short) was a man that bedded the richest women of his day: Marilyn Monroe, Zsa Zsa Gabor, Eva Peron, Ava Gardner, Barbara Hutton…to name but a few. Normally, women cling to rich men; but for Rubi, it was the reverse—he clung to rich women. By doing so, he was able to fleece millions in alimony payments. He used these payments, along with his political position, to socialize with the richest men of his day as well: Frank Sinatra, King Farouk, and most notably, President Trujillo, the former dictator of the Dominican Republic.

Much has been said about Rubirosa. But here is my takeaway(s)…

Your Appearance Matters

Rubi was an immaculate dresser. He was the stereotypical Latin lover, bedecked in expensive clothing. He was a man that wore monogrammed underwear (I laughed out loud when I read that part). In short, Rubi always “looked the part.” His impeccable style was even commented on by Sammy Davis Jr.

  • Rubi deeply impressed Sammy [Davis Jr.], who always sought to fashion a gentleman of himself, with his sartorial sense. “I have always cared about clothes, and I will go to any length to look good,” Sammy confessed. “But the way Rubirosa dressed made me feel as if I’d fallen off the garbage truck.”

The book reminded me that Americans have become too casual in their dress. Hell…people are now showing up to public places in their pajamas. It’s embarrassing. What’s been forgotten is the value of lifestyle game, the value of style.

Rubirosa with Marilyn Monroe…another notch for the Dominica cad.

Remember that water seeks its own level; so if you want to sleep with beautiful women—most of whom are dressed elegantly—then you have to improve your fashion game. Rubi reminds us that dressing well is part of a man’s package (pardon the pun); I’m currently doing a reassessment of my wardrobe as we speak.

Having a Big Dick is a Good Thing

Rubi’s member was the stuff of legend: “Yul Brenner in a black turtleneck,” as the author puts it. Levy dedicates an entire chapter to the reputation surrounding Rubi’s legendary appendage. Here are some quotes from what is, arguably, the most interesting chapter in the book:

  • There is no way around saying it out loud: The man was well hung, hung, indeed, legendarily, his superhuman endowment a calling card that recommended him in circles into which he might otherwise never have gained admittance. Women heard about it, wondered about it, whispered about it, had to see it, hold it, have it—and who was he to deny them?

Ah, to have such problems…

  • Truman Capote described it in Answered Prayers—without ever seeing it, of course—as “that quadroon cock, a purported eleven-inch-café-au-lait sinker thick as a man’s wrist.

Truman Capote…no comment.

  • His tailors were said to have a job on their hands trying to hide the thing in the folds of his famously impeccable wardrobe. And his custom-made underwear, complete with monogram, proved a bonanza to his Russian valet, who used cut pairs and sold the swatches around Paris as souvenirs.

You know you’re well hung when the tailor needs to specially design your underwear. Now I’m not sure if these rumors were 100% true (perhaps they were exaggerated a bit). But I think we can assume that Rubi was, indeed, well hung. And I have no doubt that many women were looking to confirm the rumor.

Rubi, reflecting on the beauty of being well hung

Looks Can Only Take a Man So Far

Eventually, despite all his charm, Rubi becomes a comical character: a cuckolded male, bowing to one wife after the other so he can “stay in money.” Very sad. Moreover, Rubi was largely illiterate. He had no interest in reading, writing, philosophy…in short, he lacked the Weltanschauung of a great man. He was not a hero, a leader born to inspire men.

Being well dressed and well hung can only take a man so far…

While reading the story, I reflected on how Rubi’s persona has affected, on some level, many Latino men. We’re emulative creatures. We seek heroes and the ones that are presented to us (via movies and the press) are often our first choice. I’ve know many Latin males who were much like Rubi—in short, all substance. Men who place a high value on their clothing and bedding women; men that are impeccably dressed, but have little underneath. Eventually, when the women learn that these men are Paper Alphas, the relationship implodes. I can’t help wondering how many of them took subtle “clues” from the popular legend of Rubirosa, be it on a conscious or unconscious level.


This book is a must read. Rubirosa is, for better or worse, a tremendous figure of the 20th-century. And despite his flaws, he still has many things to teach men. We can learn from his victories as well as his defeats.

I highly recommend adding this novel to your bookshelf.

4 thoughts on “Book Review: The Last Playboy: The High Life of Porfirio Rubirosa

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