Hoodwink + Monkey King

Why this works

Picking these two together looks smart because both heroes love trees. The reality is they often get in each other's way. Monkey King wants to stay perched on a tree to set up his own Primal Spring, but this same tree is the one Hoodwink needs to land a Bushwhack on an enemy below. If Monkey King jumps down to use Boundless Strike, he is now on the ground and cannot help enable Hoodwink's stun. Their abilities rely on the same terrain but for conflicting purposes, which makes their gank attempts surprisingly awkward and unreliable.

This disjointedness continues throughout the game. In teamfights, both Hoodwink and Monkey King need specific positioning to be effective, and their ideal spots rarely overlap. The duo offers similar styles of elusive damage and conditional lockdown, but they fail to compensate for each other's weaknesses. Enemy teams can often split them up or force fights away from treelines, leaving one or both heroes feeling ineffective. Instead of creating openings for each other, they frequently end up competing for the same positioning, making it difficult to execute clean kills.