Randolph, a former Marine lieutenant, forged a new path as an actor following his military retirement. His childhood among a traveling acting troupe ended abruptly when pirates slaughtered his family, driving him to enlist in the Marines and hunt their killers. After achieving vengeance, he returned to the stage, channeling his grief into performances meant to embolden audiences scarred by pirate violence.

A combat-related chest injury haunted him, worsening with age until his voice faded, compelling his retirement. His farewell performance faced disaster as three actors abandoned the troupe mid-show, only for the Straw Hat Pirates to step into the roles. Their chaotic, humor-laden improvisation underscored Randolph’s unwavering commitment to his art amid adversity.

His lifelong contempt for pirates clashed with Luffy’s presence, delaying their confrontation until the play’s conclusion. This resolve wavered when Governor—a disgraced ex-subordinate court-martialed for corruption—framed Randolph for arms trafficking to ruin his final act. The Straw Hats intervened, shielding him from Governor’s forces and dismantling the scheme.

Their actions fractured Randolph’s black-and-white morality. He rewrote his play’s climax, replacing a call for universal vengeance against pirates with a denunciation of those bearing “rotten souls,” irrespective of allegiance. The revised narrative urged resilience over hatred, championing the pursuit of justice without prejudice.

Though his promised duel with Luffy remained unresolved, their uneasy truce acknowledged a shift in Randolph’s perspective. While distrust lingered, he begrudgingly accepted that integrity could exist even among pirates, tempering his once-rigid worldview with nuance.