The Custom Tokens

The game tokens in Hefner's Monopoly set were mini sculptures—custom cast and hand-finished to represent people, objects, and symbols important to Hefner’s world. Each piece was a detailed work of art.

Notable tokens included a typewriter, a Playboy Bunny logo, a smoking jacket on a hanger, and even a mini cocktail glass. These tokens were designed and produced by professional model makers in the early 1970s, likely through Hefner’s connections in the entertainment and publishing industries. Each was unique and tailored to reflect his lifestyle and brand.

Custom Monopoly Tokens

Tokens – Included – Identified

John Dante – Longtime friend and associate known for his work with Hefner in club operations.

John Dante Token

David – Identity under research, but likely a staff member or close friend of Hefner.

David Token

Larry DuBois – A close friend and associate, captured in a miniature likeness.

Larry DuBois Token

Victor Lownes – Playboy executive in the UK; depicted in this detailed figure.

Victor Lownes Token

Shel Silverstein – The beloved poet and Playboy contributor represented here.

Shel Silverstein Token
Shelly Token

Shelly – A friend or staffer token, identity confirmed through 1970s imagery.

Gene Siskel – Film critic and regular Mansion guest; captured in miniature.

Gene Siskel Token

Playboy Bunny – The most iconic symbol of the brand represented as a token.

Bunny Token

Hugh Hefner – The man himself, rendered in token form as a tribute within the game.

Tokens – Included – Unidentified

Unlabeled object resembling an abstract sculpture.

Unidentified Token 1

Tokens – Missing

Original pipe token — last seen in 1974 photographs but not present in surviving sets.

Missing Pipe Token