Chess held the position of defense minister in King Wapol’s regime on Drum Island, orchestrating military strategies with steadfast allegiance to the monarch. When Blackbeard’s forces devastated the kingdom, he escaped alongside Wapol and Kuromarimo, later joining the Bliking Pirates to advance Wapol’s goals through piracy.

During the Drum Island Arc’s retelling, Chess aided Wapol’s campaign to reclaim the throne, wielding a massive bow with flaming arrows. His signature Checkmate attack synergized with Kuromarimo’s electrically charged projectiles, amplifying their destructive potential. Demonstrating notable resilience, he endured assaults from Lapahns—massive, tree-toppling rabbit-like creatures—during skirmishes.

At Drum Castle, Chess sought to bolster Wapol against the Straw Hat Pirates until intercepted by poisonous spores released by Wapol’s brother, Musshuru. This incapacitation prevented his fusion with Kuromarimo into Chessmarimo, diverging from established events. After Wapol’s final defeat, Chess was permanently ousted from power as Dalton ascended to govern Drum Island.

In non-canon narratives, Chess later parted ways with Kuromarimo and established a new base in the Evil Black Drum Kingdom, resuming service under Wapol. He reappeared at the Pirates Festival on Delta Island during *One Piece: Stampede*, upholding his role as a dedicated enforcer.

Chess’s demeanor blended arrogance with fierce loyalty, frequently boasting of pinpointing adversaries’ vulnerabilities while dismissing civilian harm. He rigorously enforced Wapol’s tyrannical decrees, including restrictive medical laws and violent suppression during the attempted reconquest, mirroring his ruler’s merciless governance.