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 © 2025 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

Honey Play Box Debuts 'Tressa' Vibrator

Honey Play Box introduced its new Tressa multi-stimulation, app-enabled vibrator.

Blush Debuts 2 New Glass Plugs From 'Oh My Gem' Collection

Blush has introduced two new glass plugs, Lustre and Prestige, from its Oh My Gem collection.

EP Products Founder Don Wilson Passes Away

Don Wilson, the founder of EP Products and a notable figure in Canada's adult retail community, has passed away.

Orion Debuts 'Your Strap-On' Collection From 'You2Toys' Line

Orion Wholesale has introduced the Your Strap-On collection from its You2Toys line.

Stephen Colbert Takes Aim at Texas' Crackdown on Sex Toys

Stephen Colbert is cracking up over Texas lawmakers’ crackdown on sex toys in the state.

XR Brands 'Silicone Body Forms' Highlighted at Paris Fashion Week

XR Brands’ Ripped Silicone Male Chest and Perky Pair Silicone Breasts were highlighted at 2025 Paris Fashion Week.

Eye of Love Introduces 'Matchmaker Collection' Planogram

Eye of Love has debuted a new display planogram for its Matchmaker Collection of pheromone-infused scents.

Fleshlight Debuts Taylor Vixxen Stroker

Fleshlight has introduced its new Pro stroker, molded on the anatomy of Taylor Vixxen.

Orion Expands 'LateX' Collection With 2 New Outfits

Orion Wholesale has added two new outfits to its LateX collection of fetish apparel.

Blush Debuts 'Unicorn Dreams' Vibrator

Blush has introduced the new Unicorn Dreams vibrator from its Play With Me collection.

Show More