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

Court of International Trade Rejects Trump 'Replacement' Tariffs

The U.S. Court of International Trade on Thursday ruled that President Trump’s 10% global tariff under the Trade Act of 1974, imposed after the Supreme Court invalidated the administration’s broad “Liberation Day” tariff regime, is illegal — but stopped short of a nationwide injunction against the tariff.

Blush Announces Executive Appointments

Blush has announced three new executive appointments across its organization.

Williams Trading Launches 2026 'Pride' Promo, Summer Catalog

Williams Trading has launched its 2026 Summer Pride promotion and catalog.

Magic Silk Debuts 'Rush' Collection

Magic Silk has introduced its new Rush line of lingerie.

Playharda Introduces 'AquaPulse Trio' Shower Massager

Playharda Wholesale has debuted the AquaPulse Trio shower massager with interchangeable heads.

Sportsheets Releases New Training Video for 'Shadow' Collection

Sportsheets has released its latest training video, hosted by Brand Ambassador Rin Musick, featuring the Sex & Mischief line’s Shadow Collection.

Orion Debuts 'Ultimate Sex Stool' From 'The Banger' Line

Orion Wholesale has introduced the new Ultimate Sex Stool from its Banger line.

North Carolina Weighing Tax on Brick-and-Mortar Sales of Adult Material

The North Carolina state legislature is considering a bill that would impose a new 10% tax on adult material sold by physical retailers in the state.

Lick Goods Expands Massage Oils Collection

Sexual wellness brand Lick Goods has introduced two new flavored massage oils.

Orion Expands 'Bad Kitty' Line

Orion Wholesale has added six new restraint sets to its Bad Kitty collection of fetish accessories.

Show More