Teddy Roosevelt
from Cowboys and Indians

Medium: Screenprint in colors on Lenox Museum Board
Year: 1986
Sheet: 36×36 inches (91.4 x 91.4 cm)
Edition: 250
Artist’s Proofs: 50 AP
Printer’s Proofs: 15 PP
Hors Commerce: 15 HC
Other: 10 numbered in Roman numerals
Trial Proofs: 36 TP in unique color combination
(see Feldmann & Schellmann IIB.386)
Publisher: Gaultney, Klineman Art, Inc., New York
Printer: Rupert Jasen Smith, New-York
Literature: Feldmann & Schellmann II.386

Signed and numbered in pencil lower right
With the publisher’s blindstamp and the artist’s copyright inkstamp on the reverse

Theodore Roosevelt is one of the most intellectually charged images from his late portfolio Cowboys and Indians, a series in which he revisits the mythology of the American West through the lens of mass media, historical memory, and cultural construction. Created just one year before his death, the work belongs to a period in which Warhol’s practice had reached a remarkable level of conceptual clarity, combining his signature visual language with a more overt engagement with American identity.

Portrait of Theodore Roosevelt by George Gardner Rockwood, 1898
Library of Congress Prints and Photographs Division

The composition is based on a historical photographic portrait of Theodore Roosevelt, the 26th President of the United States and a central figure in the mythology of the American frontier. Warhol isolates Roosevelt’s bust against a flat, vividly colored background, transforming a conventional presidential image into a graphic, almost emblematic figure. The sharp outlines, high-contrast tones, and bold chromatic interventions, often in unexpected combinations, detach the image from its historical origins and reframe it within Warhol’s visual system of repetition and reinvention. More precisely, Warhol used an 1898 portrait of then Colonel Theodore Roosevelt during the Spanish American War. After making headlines leading the ‘Rough Riders’ in Cuba, upon his return, Roosevelt was elected Governor of New York. In 1900, he was elected vice president on a ticket with incumbent William McKinley. And mere months later, following McKinley’s assassination, Roosevelt was sworn in as president of the United States.

Over the course of his breakneck rise to power, Roosevelt leveraged his public persona as a war hero, frontiersman, and naturalist to great political expedience. Warhol’s Teddy Roosevelt captures the figure just before his rapid political ascension, playing off the role that first garnered him national attention. Depicting Roosevelt’s face in inverted tones, Warhol calls attention to the idea, like the film negative, that this image is fundamental: that the colonel underlies the president. Often overlooked in discussions of Warhol’s presidential portraits, Warhol’s Teddy Roosevelt offers not only another stylized portrait, but a serious look at the conditions and myth of producing presidents. Teddy Roosevelt’s inclusion in Cowboys and Indians suggests the concrete, political results of America’s fascination with the West: a fascination that took him all the way to the White House…

Roosevelt’s inclusion in the portfolio is particularly significant. Unlike the Native American figures and cultural symbols also represented in Cowboys and Indians, he embodies the institutional power and expansionist ideology that shaped the American West. Warhol does not present Roosevelt as a neutral historical figure; rather, he elevates him to the status of a pop icon, placing him on the same visual plane as entertainers, outlaws, and indigenous figures. This flattening of hierarchy is central to the series: history, myth, and media are treated as interchangeable layers within a broader cultural narrative.

Teddy Roosevelt is part of Cowboys and Indians
(Click on picture below to access the Catalogue entry)

The portfolio Cowboys and Indians was published in a main edition of 250, along with a number of artist’s proofs, printer’s proofs, and trial proofs. Each print is signed and numbered, reflecting the standardized edition structure that characterizes Warhol’s production in the 1980s. Within this framework, Theodore Roosevelt stands out for its conceptual weight, anchoring the series in the political and historical realities underlying the romanticized imagery of the West. From a market perspective, works from Cowboys and Indians have gained increasing recognition among collectors, particularly as Warhol’s late prints continue to be reassessed for their intellectual depth and historical resonance.

Ultimately, Theodore Roosevelt is less a portrait than a cultural statement. Warhol transforms a figure of political authority into a reproducible image, subject to the same processes as movie stars and commercial icons. In doing so, he suggests that history itself, like celebrity, is constructed, mediated, and endlessly reproduced. The work encapsulates the broader ambition of Cowboys and Indians: to dismantle the myths of the American West while simultaneously revealing their enduring visual power.

Auction Market Overview

Regular Editions

Christie’s New-York: 15 April 2026
Estimated: USD 30,000 – 50,000
USD 82,550

ANDY WARHOL (1928-1987)
Teddy Roosevelt, from Cowboys and Indians, 1986
(Feldman & Schellmann II. 386)
Screenprint in colors on Lenox Museum Board
Signed in pencil, numbered 223⁄250 (there were also 50 artist’s proofs)
Published by Gaultney, Klineman Art, Inc., New York
With the artist’s and publisher’s copyright ink stamps on the reverse

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Rago: 15 October 2025
Estimated: USD 30,000 – 50,000
USD 88,900

Lone Star Art Auction: 12 October 2024
Estimated: USD 70,000 – 90,000
USD 96,000

ANDY WARHOL (1927-1987)
Teddy Roosevelt (FS II.386), 1986
Screenprint on Lenox Museum Board
Signed lower right: Andy Warhol 70/250

Coeur d’Alene Art Auction: 27 July 2024
Estimated: USD 30,000 – 50,000
USD 229,900
AUCTION RECORD FOR TEDDY ROOSEVELT

ANDY WARHOL (1928 – 1987)
Teddy Roosevelt (1986)
Screenprint on board
Signed and numbered 236/250 lower right

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Grogan & Company: 6 May 2023
Estimated: USD 30,000 – 50,000
USD 62,500

ANDY WARHOL (American, 1928-1987)
Teddy Roosevelt, from Cowboys and Indians (F&S II.386), 1986
Screenprint in colors on Lenox Museum Board
Signed Andy Warhol lower right and numbered 44/250 lower left
With publishers blind stamp lower left and stamp verso

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Hindman: 29 September 2022
Estimated: USD 20,000 – 40,000
USD 75,000

ANDY WARHOL (1928–1987)
Teddy Roosevelt (from Cowboys and Indians), 1986
Screen-print on Lenox Museum Board
Signed and numbered 71/250 in pencil

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Bonhams New-York: 26 May 2021
Estimated: USD 22,000 – 28,000
USD 56,562

Trial Proofs

Teddy Roosevelt (TP 8/36), 1986

Heritage Auctions: 19 April 2022
Estimated: USD 25,000 – 35,000
USD 131,250
TRIAL PROOF

ANDY WARHOL
Teddy Roosevelt (F. & S. II.386), from Cowboys and Indians, 1986
Screenprint in colors on Lenox Museum Board
Signed in pencil and inscribed ‘TP 27/36’
A unique color trial proof, aside from the numbered edition of 250