Grimstroke + Shadow Fiend

Why this works

Landing a double-hero Requiem of Souls with Grimstroke's Soulbind is the dream, but it's much harder to execute than it sounds. For it to work, Shadow Fiend has to be right on top of two enemies, which is an extremely dangerous place for him before he gets his core items. While Grimstroke can set this up, the risk for Shadow Fiend is massive. The more common and reliable play is using Ink Swell's stun to guarantee Shadowrazes, which helps in skirmishes but isn't a game-defining combo on its own.

Across the game, there's often a disconnect in timing. Shadow Fiend is a fragile core who needs to farm his first major items, like a Black King Bar, before he can confidently fight. He wants to avoid difficult engagements. Grimstroke, however, is a proactive support who is constantly looking for opportunities to cause chaos with Ink Swell. This can lead to situations where Grimstroke is ready to fight but Shadow Fiend isn't, or SF gets caught out because he was forced into a fight too early. They can certainly win fights together, but they don't naturally enable each other's game plans.