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Shocking news out of San Diego Comic-Con and Marvel’s big Hall H panel Saturday night: Captain America: Brave New World looks to be taking on the best Cap comic book run of all time! That’s right, baby, the supervillains have unionized.
Giancarlo Esposito, the consummate badass that everyone assumed would be playing someone befitting his menace, like GW Bridge, William Stryker, or even Magneto, turns out to be playing none of those characters. Instead he’s playing a mild-mannered economics professor and notorious Marvel Universe labor leader from Kenosha, Wisconsin. Probably. Maybe? Let’s unpack the surprisingly complicated backstory of Sidewinder, aka the King of the Serpent Society!
Who Is Giancarlo Esposito’s Sidewinder?
Marvel Studios’ panel confirmed that Esposito would be playing Sidewinder, King of the Serpent Society. However, it’s unlikely they’re doing a direct lift from the comics, because it would be a deeply bizarre pull to puzzle together. Let us explain.
There have been three Sidewinders in Captain America comics. The first, and best, was introduced in Marvel Two-in-One #64 by Mark Gruenwald and Ralph Macchio in 1980. His real name was Seth Voelker and he was an economics professor who couldn’t get tenure, so he was hired by an evil corporation called Roxxon and quickly discovered they were very bad dudes. His punishment for this discovery was to be sent to steal the Serpent Crown, a MacGuffin of unimaginable power. After succeeding, he was given access to a teleportation cloak and the means to control it with his mind, which led him to adopt the snake-themed name Sidewinder, and, following a break with Roxxon, to create the first labor union for supervillains.
Sidewinder comes off through much of the run as kind of a weasel, but eventually he gets out of the supervillaining game after convincing Captain America to help him put together money to help his sick daughter, makes a full face turn from villain to antihero. He then retires happily and healthily.
Sidewinder 2 was not so lucky. In 1998’s Iron Fist #1, a new Sidewinder was recruited to steal the Zodiac Key from a SHIELD installation and he died. Like, right away.
The third Sidewinder has been mostly a chump. Gregory Bryan was introduced in 2004’s Captain America #31 by Robert Kirkman and Scot Eaton. He’s a throwaway character in that issue, but we later discover he’s been given the same power suite by the Brand Corporation. He then spent the next 20 years getting smacked down by various superheroes (like Sam Alexander, the most recent Nova) and playing the old hits (reassembling the Serpent Society during Secret Empire).
Bryan plays mostly as a stock villain, meant to be a little more colorful but serve the same narrative purpose as Cap beating on a few henchmen. Voelker, however, was absolutely fascinating in that he was an extremely regular guy press-ganged into villainy who tried to make the best of it.
And there’s one other sign that Brave New World might be lifting more from that Gruenwald era Serpent Society than you’d guess by Esposito’s casting: Diamondback. Rosa Salazar is expected to play one of Cap’s most fascinating love interests, the reformed Serpent Society member Diamondback, in the new flick. That relationship was established during Gruenwald’s seminal run, and while it was Steve Rogers in that relationship in the comics, Anthony Mackie’s Sam Wilson can definitely pull off the “he’s so nice I would give up crime for him” thing that worked on the page.
And if that’s foundational for the new movie, then it’s not impossible that they’re making Esposito into a snake-themed Jimmy Hoffa. Stay tuned.
Captain America: Brave New World opens on Feb. 14, 2025.
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