8. The Winter Solider (Captain America: The Winter Soldier)

Captain America: The Winter Soldier boasted an impressive cast and with that an impressive roster of bad guys. In the same vein as the movie itself, these weren’t completely evil characters, but good characters morally and psychologically corrupted. Robert Redford’s Alexander Pierce was another contender for this list, a senator imbued with power and the sense of moral righteousness that almost lead the deaths of thousands and the fall of SHIELD itself. But one character beats him; Bucky Barnes, AKA the titular Winter Solider.

From Steve Rodgers wholesome best friend to an assassin responsible for the murder of key MCU characters like Howard Stark (and almost Nick Fury) he is a mental and physical match for Captain America and their shared friendship almost becomes the hero’s undoing. His redemption in Captain America: Civil War is going to be an interesting one, particularly where Tony Stark / Iron Man gets involved. But as the villain of Cap’s second movie he stands out as one the best bad guys in Phase 2.