Exceptional Group of Warhol Prints—Led by Cowboys and Indians—to Anchor Freeman’s | Hindman Spring Auction

Freeman’s | Hindman is pleased to announce the spring auction of Prints and Multiples taking place May 7 in the firm’s Chicago saleroom. The sale features an exceptional selection of works by Modern and Contemporary masters, led by Andy Warhol’s complete Cowboys and Indians portfolio (1986), alongside standout prints by Picasso, Lichtenstein, Longo, and others.

Warhol’s Cowboys and Indians: A Late-Career Masterpiece

The centerpiece of the auction is Andy Warhol’s complete Cowboys and Indians portfolio, estimated at $600,000–800,000 (Lot 20). Created just before his death, the ten-print portfolio explores the mythology of the American West, juxtaposing figures like Geronimo and General Custer with commercial icons such as John Wayne. 

Commissioned by publishers Edmund Gaultney and Kent Klineman, the portfolio reflects Warhol’s signature Pop sensibility while critiquing the way media and consumerism have shaped public perception of Indigenous cultures and historical figures. The vibrant colors, bold outlines, and layered imagery underscore Warhol’s ability to transform serious cultural subjects into striking visual commentary. This portfolio stands as a powerful exploration of America’s historical myths and their lasting impact on contemporary culture. 

“We are thrilled to bring this fresh-to-market Cowboys and Indians portfolio to auction. In the same family since 1986, it is in pristine condition with bright, fresh colors,” says Monica Brown, Head of the Prints and Multiples department. “This set would be a cornerstone acquisition for any Pop or Western Art collection.”

Additional Warhol Highlights

 
Andy Warhol, Tomato Soup (from Campbell's Soup I), 1968 | Estimate $50,000–70,000
Andy Warhol, $ (4), 1982 | Estimate $80,000–120,000

Also featured is Warhol’s Martha Graham portfolio with an estimate of $60,000–80,000 (Lot 24), commemorating the legendary dancer with three expressive screenprints: Satyric Festival Song, Lamentation, and Letter to the World (The Kick) (all 1986). Based on photographs by Barbara Morgan, the series captures Graham’s dynamic emotional expression and lasting influence on modern dance.

Further Warhol prints include:

• Lot 21 | Tomato Soup (from Campbell’s Soup I), 1968
  Estimate $50,000–70,000
• Lot 22 | Chicken Noodle Soup (from Campbell’s Soup I), 1968
  Estimate $30,000–50,000
• Lot 23 | $ (4), 1982
  Estimate $80,000–120,000
• Lot 25 | After the Party, 1979
  Estimate $20,000–30,000

Robert Longo’s Men in the Cities

Robert Longo, Edmund (from Men in the Cities), 1985 | Estimate $25,000–35,000
Robert Longo, Anne (from Men in the Cities), 1985 | Estimate $25,000–35,000

Two dynamic works from Robert Longo’s celebrated Men in the Cities series— Edmund and Anne—will be featured in the sale, each estimated at $25,000–35,000 (Lot 7 and Lot 8). These striking lithographs depict sharply dressed figures caught in moments of dramatic, almost balletic motion.

To create the series, Longo photographed friends—including art world luminaries like Cindy Sherman and Larry Gagosian—reacting to sudden physical stimuli on the rooftop of his New York studio. The resulting images, with their exaggerated poses and high contrast, became icons of 1980s art, capturing a sense of urban intensity and emotional tension.

Modern Masters and Picasso's Muse

Pablo Picasso, Jacqueline au Bandeau de Face (Grand Tête de Femme), 1962 | Estimate $70,000–90,000

The Modern section features strong offerings by Pablo Picasso, Salvador Dalí, Joan Miró, Henri Matisse, and M.C. Escher. A highlight is Picasso’s striking linocut Jacqueline au Bandeau de Face (Grand Tête de Femme), 1962 (Lot 75), estimated at $70,000–90,000. Depicting his wife and muse Jacqueline Roque in a Cubist style, the portrait blends multiple perspectives into a single, commanding image.

Additional Highlights Include:

• Lot 12 | Roy Lichtenstein, Oval Office, 1992
  Estimate $40,000–60,000
• Lot 14 | Richard Diebenkorn, Two Way II, 1982
  Estimate $8,000–12,000
• Lot 18 | Alex Katz, Peonies, 2021
  Estimate $12,000–18,000
• Lot 51 | M.C. Escher, Sun and Moon, 1948
  Estimate $20,000–30,000
• Lot 65 | Joan Miró, Galathée, 1976
  Estimate $20,000–30,000

Sale Preview

The sale preview will be open by appointment at Freeman’s | Hindman’s flagship Chicago showroom at 1550 West Carroll Avenue.