Hugh Hefner Pens Farewell Column to Chicago

CHICAGO — Playboy founder Hugh Hefner has officially said goodbye to the city where his empire was born.

The iconic publisher wrote a farewell column in the Chicago Tribune this past weekend as the company's operations head to Los Angeles.

Brief, but poignant, Hefner chronicled the history of Playboy and thanked Chicago for helping shape the magazine.

Hefner talked about how in 1952, his tough self-introspection led to a tearful decision to make a change, ultimately leading to the founding of Playboy magazine.

“Weeks later I sat at an old card table in my Hyde Park apartment and began assembling what would become Playboy. The idea for a sophisticated and sexy men's magazine came to me some time earlier. I had already enjoyed some publishing success with That Toddlin' Town: A Rowdy Burlesque of Chicago Manners and Morals, my cartoon sendup of the Windy City's demimonde. I had recently left my copywriter's job at Esquire magazine after refusing to relocate to New York City from Chicago,” Hefner wrote.

With $8,000 of borrowed money and a Marilyn Monroe photo bought from a calendar company, Hefner launched Playboy magazine in 1953. “I roamed newsstands around Chicago and watched readers, delighted when I witnessed someone pick up and buy a copy,” Hefner said.

The idol of millions of urban men (or those who simply fantasized about the Playboy lifestyle), Hefner went on to describe how Chicago represented a true post war America brimming with men seeking ideas “that challenged their socially conservative surroundings. Interested in more than work and domestic security, longing for sexual adventure and enjoying the postwar financial boom.”

Hefner pointed out that the new urban man looked to "spurn the restrictions of puritanical convention in favor of life as a single, city-bred male with a bachelor apartment and a proper martini." 

"I counted myself among them. Playboy's success proved I wasn't alone,” he said.

The magazine’s early success surpassed Hefner’s wildest dreams and allowed him to move into a mansion on Chicago’s tony Gold coast and open the first Playboy Club in 1960. The company ultimately made its headquarters in the iconic Palmolive building on Michigan Avenue in 1965 with nine-foot illuminated letters spelling out "Playboy."

Hefner thanked Chicago in his column: “Now, after nearly 60 years, the Playboy offices in Chicago have closed as we consolidate our operations in Los Angeles. It is bittersweet to see Playboy leave the city I love. It's where I grew up, and where my two oldest children were born.

“Chicago provided the magazine's connection to the true American male, and in return I like to think the magazine's presence provided the city with an edge, a reminder to the rest of America that the first steps of a sexual revolution took place at a card table at 6052 S. Harper Ave., ran wild in a State Street mansion and grew into a global presence on Michigan Avenue visible to anyone driving down Lake Shore Drive. Together we took those ideals of sexual liberation from Loop newsstands to the farthest edges of the planet. Playboy could not have happened anywhere else but Chicago.”

Related:  

Copyright © 2026 Adnet Media. All Rights Reserved. XBIZ is a trademark of Adnet Media.
Reproduction in whole or in part in any form or medium without express written permission is prohibited.

More News

2026 XMAs: Watch the Global Live Broadcast

The 2026 XMAs, presented by Fansly, will stream live to a global audience via the official event website, welcoming fans worldwide to join a celebration of excellence in adult entertainment.

Magic Silk Expands 'Exposed' Line With 'Blue Sky' Collection

Magic Silk has expanded its Exposed line of lingerie with the Blue Sky collection.

Male Power Debuts 'Fishnet 2.0' Collection

Male Power has introduced its new Fishnet 2.0 collection of men's underwear.

OTouch Announces '2nd Generation' Masturbators

OTouch has announced the launch of its second-generation strokers.

Orion Unveils New 'Kink Royal' Collection From 'Noir Handmade' Line

Orion Wholesale has introduced the Kink Royal collection from its Noir Handmade line.

Williams Trading Releases 2026 'Valentine's Day Essentials' Catalog

Williams Trading Co. has released its new 2026 Valentine’s Day Essentials catalog.

Le Wand 'Lick' Vibrator Featured in Wired Review

Le Wand's Lick three-in-one vibrator is featured in a new review on Wired.com.

We-Vibe Debuts 2 New Vibrating Cock Rings

We-Vibe has introduced its new Pivot 2 and Verge 2 vibrating cock rings.

Lovense Debuts 'Lush Anal' Vibrator

Lovense has introduced its new app-controlled Lush Anal vibrator.

Orion Debuts 'Rabbit With Thrust and G-Spot Stimulation' Vibe From Sweet Smile Line

Orion Wholesale has introduced the Rabbit Vibrator with Thrust Function and G-Spot Stimulation from its Sweet Smile line.

Show More