It’s usually hard to pinpoint the exact moment a bright star goes supernova. But Muhammad Ali did that very thing in April 1968, thanks in large part to Esquire magazine’s cover of the world’s most famous and controversial athlete “dressed” as St. Sebastian, the third-century Christian martyr. In hindsight, Ali-as-St. Sebastian was both a stroke of genius and an obvious creative move. Ali’s conversion to Islam in 1964 — and his affiliation with the Nation of Islam and its controversial leader, Elijah Muhammad — made mainstream white America deeply suspicious of the champ. At the time of the photo shoot, Ali had already been stripped of his heavyweight boxing title after refusing to be drafted into the Army and denied a license to fight anywhere in the country. The ban would last from the time he was 25 until he was almost 29 years old — the prime of a boxer’s physicality. Ali was surely suffering the slings and arrows of outrageous fortune, as Shakespeare had written, and George Lois, Esquire magazine’s art director (and the reputed inspiration behind Mad Men’s Don Draper), certainly knew his Hamlet and how to make a legend that much more legendary. Subtitled “The Passion of Muhammad Ali,” the cover image set the standard for modern magazine creative moxie. The day of the photo shoot, which took place in longtime Esquire photographer Carl Fischer’s New York City studio, Lois showed Ali a postcard of a St. Sebastian painting by the 15th century Italian artist Francesco Botticini. Ali liked the idea of the photo shoot but had misgivings about posing as a Christian. Fischer put in a frantic, last-minute phone call to Herbert Muhammad (Elijah Muhammad’s son) in Chicago, and he gave his consent for Ali to take part in the Christian symbolism. Lois had the idea to place six arrows onto Ali’s torso and leg: deadly wounds. Ali’s hands were placed behind his back and his face was turned upward, as if looking to heaven. Fischer shot the photo on color film; The backdrop is stark white, as are Ali’s satin boxing shorts, shoes and socks. The Esquire logo and waistband of the Everlast shorts are black. Red blood runs down Ali’s brown skin, which has a warm glow from Fischer’s studio lights. Fischer told Esquire in 2015 that the legendary photo shoot was a straightforward affair, except for the arrow props: “We’d practiced on a model beforehand, and when we tried sticking the arrows on the body with glue, they were so heavy that they hung down. So we put a bar across the studio’s ceiling and hung fishing line to hold up the arrows. It was a pain in the ass, because Ali had to stand very still for a long time, till we got all the arrows lined up at the right height. He didn’t complain, though. He was one of the few people in public life who was just like his reputation. He was funny. He was relaxed. He wasn’t a bulls——.” In the wake of Ali’s death in 2016, Lois shared more details of the shoot with Rolling Stone: “… Ali posed for the photo while Lois’s team attached six arrows to his body to mimic the Botticini painting. The champ quickly internalized the martyr conceit. Lois remembers that during the shoot, “Ali said, ‘Hey, George ….’ which always meant he wanted to talk. He took his right hand out from behind his back and pointed at each of the arrows. And then he’d say the names of the people in this world that were out to get him. He’d point to one arrow: ‘Lyndon Johnson.’ The next one: ‘General [William] Westmoreland [who led the Vietnam operation].’ Then: ‘Robert McNamara.’ Each of the arrows [was] a person in the government that had hurt him.” Dudley Brooks, assistant photo editor for The Washington Post and former photo editor of Ebony, says Ali’s Esquire cover was the perfect storm of Madison Avenue creativity, the acknowledgment of the historic impact that the civil rights movement was having on the world and the willingness of Ali to shoulder the burden of a corrupt political system. “At the time, Ali was hated by the establishment and was thoroughly controversial within the mainstream,” Brooks noted. Esquire had taken on important social movements before, but this was the first time white America was seeing Ali this way. Remembering The Champ “Black folks were convinced that Ali was being put up as a sacrificial lamb,” Brooks continued. “But George Lois and Carl Fischer were pushing the idea out to white America in a very bold way, which says a lot about Esquire’s bravery during that era.” Lois had trodden that territory before. In December 1963, he came up with an idea for an Esquire cover that featured another controversial black athlete: heavyweight champion boxer Sonny Liston wearing a red-and-white cap as “The First Black Santa.” America in 1963 was, of course, a hotbed of racial tension and anxiety. It was the year of Medgar Evers’ murder, black demonstrators in the South being attacked by police with firehoses and the attempt by segregationist Gov. George Wallace to block black students from enrolling in the University of Alabama. President John F. Kennedy’s assassination in November 1963 had shaken the country to its core. Sports Illustrated famously recalled years later that the steely-eyed Liston looked like “the last man on earth America wanted to see coming down its chimney.” Advertisers pulled $750,000 in ads, subscribers bailed, and angry readers wrote in. But the Liston cover controversy was ultimately good for business and gave the editorial team a taste for creative chance-taking that defined Esquire during the 1960s. “George’s influence as an art director was his often aggressively oratorical approach to what was happening in America during the ’60s,” said Arem Duplessis, former design director of The New York Times Magazine and current design director at Apple. Every Esquire cover that Lois did during that time “is a collector’s item, worthy of a frame. But most importantly, they were a brave interpretation and/or reflection of culture during some extremely turbulent times.” “George gave little to no f—s,” Duplessis said. “I imagine he had similar pressures to what magazines face today, including the general rule of not pissing off the advertisers. George either had a free pass or he simply didn’t care. I go with the latter. I truly wish today’s editors were willing to take some of the same risks.” The influence of Ali’s St. Sebastian cover is still being felt, even one year after his death. Controversial magazine covers still draw attention, especially on newsstands, and serve as a kind of advertising for the brand. And a single image of the biggest celebrity of the day, which Ali was during the late ’60s, that encapsulates the essence of a person (and an era) remains an essential mission.