In December of 2018, Collider hosted a Q&A with the Russo Brothers about Avengers: Infinity War and they were asked if Hugo Weaving ever came close to reprising his role as the Red Skull. Anthony Russo said, “He was asked.” And now we know Weaving’s side of the story.
In an interview with Time Out, Weaving explains why he didn’t return:
‘Oh, yeah. I loved playing that character Red Skull – it was a lot of fun. We were all obliged to sign up for three pictures: I was thinking [Red Skull] probably wouldn’t come back in “Captain America” but he may well come back as a villain in “The Avengers”. By then, they’d pushed back on the contracts that we agreed on and so the money they offered me for “The Avengers” was much less than I got for the very first one, and this was for two films. And the promise when we first signed the contracts was that the money would grow each time. They said: “It’s just a voice job, it’s not a big deal”. I actually found negotiating with them through my agent impossible. And I didn’t really wanna do it that much. But I would have done it.’
His comments there pretty much put to rest the internet theories that the was done playing genre roles and that’s why he didn’t come back. He also says in the interview that he won’t be Agent Smith in the fourth Matrix movie due to a scheduling conflict.