Among the numerous adversaries who have faced off against Captain America, the Serpent Society, a group of mercenaries with a snake motif, stands out as some of his most dangerous enemies. The Serpent Society made its first appearance in 1985 within the pages of “Captain America” #310, crafted by writer Mark Gruenwald and artist Paul Neary. This group was assembled by Sidewinder with the intention of offering their illicit services to villainous organizations such as Hydra, Advanced Idea Mechanics (A.I.M.), and the Maggia.

Over time, the Serpent Society has manifested in various forms, making appearances in comic books, video games, animated series, and even a novel. In 2025, they eventually made their way into the Marvel Cinematic Universe, appearing in “Captain America: Brave New World.” However, this event was preceded by a long and winding journey to the silver screen. Some devoted MCU fans might recall that in 2014, Marvel Studios president Kevin Feige hinted at a third “Captain America” film titled “Serpent Society,” which ultimately served as a diversion for the unveiling of 2016’s “Captain America: Civil War.”

“Captain America: Brave New World” introduces audiences to Seth Voelker, also known as Sidewinder (portrayed by Giancarlo Esposito), the leader of a lethal special ops group called “Serpent.” This team engages in conflict with Sam Wilson (Anthony Mackie), who takes up the mantle as the second Captain America. The portrayal of Serpent in the film is more subdued compared to their comic book version, lacking the flamboyant costumes, extravagant technology, and even several key members. Notably, scenes featuring Rosa Salazar as the pink-haired mercenary Diamondback were cut from the final production. For those curious about the group’s origins in the comics, here is a detailed explanation of the Serpent Society’s history.

Unlike other villainous teams such as the Legion of Doom and the Masters of Evil, whose ambitions reach for world conquest, the Serpent Society was conceived as something unique in comic book lore: a labor union. In “Captain America” #310, Sidewinder extends an invitation to over a dozen supervillains—each with snake-related aliases, outfits, or abilities—to join forces, offering salaries, healthcare benefits, pensions, and even prison escapes facilitated by Sidewinder’s teleportation cloak.

The Serpent Society quickly demonstrates its proficiency in crime by successfully assassinating the malevolent M.O.D.O.K. for A.I.M. Despite this victory, their roster remains unstable—Princess Python departs due to her lack of superpowers, Death Adder is killed by the vigilante Scourge of the Underworld, and Viper (also known as Madame Hydra) usurps control of the group as part of a larger scheme to transform the populace of Washington D.C. into reptilian creatures.

The team’s cohesion crumbles in “Captain America” #380. They uncover the fact that Diamondback, a free-spirited mercenary, has been involved in a clandestine relationship with Steve Rogers. Accusing her of fraternizing with the enemy, the group holds a trial. Diamondback manages to escape her impending execution with the help of her allies Asp and Black Mamba, who defy the group and call upon their former leader, Sidewinder, for assistance. Consequently, the Serpent Society disbands, with many members either captured by Captain America, operating independently as mercenaries, or, like Diamondback, attempting to turn over a new leaf.

What remains of the Serpent Society sheds its skin and rebrands itself as Serpent Solutions, under the new leadership of Pit Viper (as the Marvel Universe has a seemingly endless supply of snake-based supervillains). Posing as a more legitimate business, this purely capitalistic incarnation of the team does the dirty work for billionaires and big corporations, and it inevitably tussles with the new Captain America, Sam Wilson.

An even darker path lies ahead for the former Serpent Society. In 2022’s “Avengers” #55, Serpent Solutions falls under the corrosive power of the demon Mephisto, whom they worship as the “Great Red Serpent.” Possessed by a supernatural bloodlust, they kill every civilian in their office building and offer them as human sacrifices to Mephisto, though the ritual is interrupted by the Avengers.

In the 2024 “Avengers Assemble” miniseries, Pit Viper’s team — still under Mephisto’s influence — commits several heists to gather the ingredients for the Serpent’s Tears, a deadly and supernatural poison. Pit Viper exposes Steve Rogers to the Serpent’s Tears, transforming him into a mutated and feral “Cap-Snake,” but the Serpent Society falls under the combined might of the Avengers. Captain America is healed and the Serpent Society is sent to the Hague — an ignoble fate for an organization once formed for the dubiously honorable purpose of giving super-villains labor rights.