Simpson, then 30, showed up without a football or a jersey, and Warhol had to scramble to find a ball. That Polaroid shoot led to 11 silkscreen portraits; one of them is now going on auction for the first time.

Signed by both men, the portrait is billed by the auction house as a work that brings together two of the most recognizable names of the 20th century and captures “a trajectory of celebrity and tragedy.”

“Warhol certainly could never have imagined how differently the image would come to be viewed, nor the controversy that still lingers around its subject today,” said Robert Manley, cohead of 20th-century and contemporary art at the Phillips auction house, which is auctioning the work May 16.

It was almost two decades after Warhol’s photo shoot, in 1995, that Simpson—who had retired from the NFL in 1979 and pursued an acting career—was acquitted of the double slayings of his ex-wife, Nicole Brown Simpson, and her friend Ronald Goldman. He was later found liable for the deaths by a California civil court jury that ordered him to pay $33.5 million to the victims’ families.

In a separate case more than a decade later, Simpson was convicted by a jury in Las Vegas for leading five men, including two with guns, in a 2007 confrontation with two sports collectibles dealers in a cramped room at an off-strip Las Vegas casino hotel. Simpson served nine years in a Nevada prison for armed robbery. He was discharged from parole in December 2021.

Manley noted that almost five decades after Warhol made it, the portrait still evokes a strong reaction.

“Those who view the image of Simpson staring directly down the camera are likely to recall the other notorious picture of the celebrity—his mug shot,” Manley said. “Juxtaposing these two images, created at such different points in Simpson’s life, shows a fascinating trajectory of celebrity and tragedy.”

Commissioned as part of the broader “Athletes” series that included Muhammad Ali, soccer star Pelé, tennis star Chris Evert, golf’s Jack Nicklaus, and figure skater Dorothy Hamill, among others, by Warhol friend and collector Richard Weisman, this particular portrait spent 19 years at the Pro Football Hall of Fame in Canton, Ohio, where it was donated in 1992 and, according to a spokesperson there, never displayed.

In 2011, it was deaccessioned—or permanently removed from the collection—and sold to an anonymous collector in a private sale through Christie’s, with proceeds going to fund preservation of other items in the hall’s collection, said spokesperson Rich Desrosiers. Phillips estimates the portrait will sell in the $300,000 to $500,000 range. As with any of the athletes in the series, Simpson would not have existing rights to proceeds, the auction house said.

The highest price achieved at auction for one of Warhol’s Simpson portraits was $687,000, sold in 2019.

Warhol photographed Simpson in Buffalo on Oct. 19, 1977. According to the auction catalog, a quote from Warhol’s diary that day reads, “He had a five-day beard, and I thought the pictures would be awful.” Warhol died in 1987 at age 58.

The work will be on public display May 6–15 in New York before being auctioned.