Middletown Author Pens Biography of Playboy Empire's Second in Command

Anthony Valerio's new book details his friend's social climbing from humble beginnings to Hugh Hefner's mansion, where he lived for 26 years with 40 of the world's most beautiful women.


Longtime Middletown resident and author Anthony Valerio's new book, "John Dante's Inferno: A Playboy's Life," explores the life of the Playboy empire's second-in-command, John Dante, who lived a bachelor's fantasy.

Dante was a friend of Valerio's who died in 2003 and led a remarkable life: an immigrant who came to Chicago at age 2 and rose to become Playboy mogul Hugh Hefner's right-hand man.

Well-known hildren's book Shel Silverstein, also a friend of Valerio's who passed in 1999, and a good friend of John's, asked him to help John write his book. "John Dante's Inferno: A Playboy's Life," is a result of those friendships, Valerio says.  

Dante went from his humble beginnings in a small Italian village to the Playboy Mansion, where he lived for 26 years with Hugh Hefner and 40 of the most beautiful women in the world.

Dante was a key figure in the first years of the Playboy empire, hiring Bunnies, training Bunny Mothers, and managing the Playboy jet. He befriended some of the most popular and important figures of our time, including Hefner, of whom John paints as a "fascinating, complex man," as well as Silverstein, Lenny Bruce, Don Adams, James Caan and myriad other personalities and stars.

Valerio offers Middletown Patch readers an exclusive excerpt from the book:

Meeting Hugh Hefner in a Chicago nightclub Dante’s Inferno, 1959

Around 8 o’clock, Renée called up:

“Hugh Hefner just came in.”

He was still upstairs in his office. “You have got to be kidding.”

“No. He’s here with another guy.”

So he went down and saw and heard the buzz of Dante’s Inferno’s first customers’ eyes and mouths wide open, looking and pointing at Gustav Doré’s scenes of Hell. Though Playboy magazine was already a big success, Hugh Hefner’s visage was not as yet well known.

John Dante writes:

“Two guys stood together, one wearing an elegant black mohair suit and the other in penny loafers and white socks and a kind of Brooks Brothers jacket and maybe a cardigan sweater.”

The tallish guy in the mohair suit looked the part of a playboy so he extended his hand to the one whom he believed was Hugh Hefner. Then he said it for the first time:

“Hi, I’m John Dante.”

He had signed the invitations Johnny Dante to go along with the place.

“It made sense promotionally because if I had signed them ‘John Aimola,’ people would have said, ‘Who the fuck is John Aimola?’ I’m reinventing myself. I was thinking of Humphrey Bogart who is Ricky Blaine in the film Casablanca. I was picturing myself this kind of entrepreneur.”   

He had extended his hand to the wrong man, Victor Lownes, who shook it nonetheless and said:

“No, this is Hugh Hefner.”

John Dante turned and looked into Hugh Hefner’s face for the first time. He was “thin, almost emaciated, and I saw an integrity, a forthrightness, an honesty. He looked straight at you when he spoke.”

He extended his hand to the right guy and said again, confirming his transformation from an ordinary Italian to one with a famous name and name of his classy establishment—

“Hi, I’m John Dante.”

Valerio is the author of eight books of fiction and nonfiction. His short stories have appeared in the Paris Review and in several anthologies and readers. He was a book editor in major publishing houses, including McGraw-Hill. He has taught writing at NYU, CUNY and Wesleyan University. He lectures widely in the United States and Europe.

He has been a fiction judge on PEN’s Prison Writing Committee and is a member of the Author’s Guild.

The book is available on Amazon in paperback ($10) and e-book versions.

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