Leshy was used to... not quite surprises but variations in his Challengers. There were those who were collected and thoughtful, planning moves turns in advance and observing the board with an intense focus; there were the Challengers who were brash and reckless, playing cars without a second thought.

Some were prideful and confident in their abilities, while others were timid, unassuming things, always second guessing their moves.

Then there was the physical form of the Challengers. Wooden, doll-like bodies with just enough joints to move around his cabin in jerky motions. Bodies imitating the small, wooden figurines used on his map.

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Alright, it's implied that you know who Leshy is and you're a player from the real world (like someone playing Inscryption through Steam or whatever). Some ideas for roleplaying with him:

-Terrified of him. You know what he does to those who lose against him and you don't want to become a card because he cheated. Total panic attack/mental breakdown.

-Fascinated with him. You bound right over to him and start rambling, no fear at all. His goat legs are so cool and why are your eyes orange, Leshy?

-You're basically feral. Throw things at him, wreck his cabin. There's a handy little Grimoire of Sigils somewhere behind you and you can definitely try to bludgeon him with it.