Christie’s has announced that The Guilt of Gold Teeth, a masterpiece by Jean-Michel Basquiat, will be the top lot of its 21st Century Art Evening Sale, taking place on November 9 at Rockefeller Center in New York. Bidding for the nearly-14-foot-wide work will start at around $40 million, a Christie’s spokesperson told ARTnews, although an estimate is only available upon request.

Held for a nearly quarter century in a private collection, this rare and monumental 1982 canvas was created at the peak of the iconic artist’s career. This stands as an incredible example of a very limited group of career-defining works that Basquiat painted during a trip to Modena, Italy in March of 1982. The eight paintings created by Basquiat in Modena in 1982 remain some of his greatest artistic achievements, with two having established record breaking results at auction. Five years ago in May of 2016, Untitled set a world auction record, selling for $57.3 million at Christie’s New York and Profit sold for $5.5 million at Christie's New York in 2002, establish a record for the artist at the time, which remained unbroken until 2007.

It will be unveiled publicly at Christie’s Los Angeles, where it will be on view from October 14-17. It will then travel to Hong Kong where it will be on view from October 25-26 before returning to New York, where it will be on view from October 30 – November 9 ahead of the auction.

Ana Maria Celis, Christie’s Senior Vice President, Senior Specialist, and Head of 21st Century Art Evening Sale, remarked, “Painted in Modena when the artist was at the young age of 22, The Guilt of Gold Teeth represents an absolutely pivotal moment in Basquiat’s career. For the first time, he was exhibiting internationally, while simultaneously coming to a cultural reckoning with his own identity as a Black American. Through the inclusion of Baron Samedi, a key figure in Haitian Vodou, this work pays homage to his father’s heritage. Stunning, impactful, and rare, The Guilt of Gold Teeth has not come to auction since 1998 [when it sold for around $400,000]. We are beyond thrilled to present it as the top lot in our November 21st Century Art Evening sale this season.”

The central figure in this example is identified as Baron Samedi, a spirit of Haitian Vodou and leader of the Gede – who tends to shepherding departed souls to the ‘other side.’ Versions of this figure appear in several of Basquiat’s paintings, and The Guilt of Gold Teeth is one of the earliest depictions. Baron Samedi is linked closely with death, revelry, and safekeeping. He is frequently depicted as a skeletal figure dressed in funeral attire, including his signature top hat. He is both a protective caretaker as well as a riotous trickster, representing multitudes—just as much about life as about death.

Basquiat traveled to Modena for the first time in 1981; a fresh face on the art scene, the young artist was given his first one-man show under the name ‘SAMO’ at Emilio Mazzoli’s gallery. On the artist’s second trip to Modena in the spring of 1982, Mazzoli provided him with a large studio space and his artistic practice made a palpable shift. For the first time, the epic scale of his canvases allowed him to express the full scope of his artistic ambitions, while at the same time replicating the urban canvases offered up to him by the buildings of New York, where he developed his highly original artistic language. It was also at this moment that Basquiat’s body of work began to form a collective narrative around his experience as a Black man in America, while still maintaining his signature graffiti style, rife with coded nomenclature and symbolic linguistic elements (for example, ‘ASPURIA’ is thought to be a playful subversion of the Italian word aspirare, which means ‘to aspire’).