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He is first encountered as a shadowy figure in the Senton Splash Tunnel of Santa Destroy, on Travis' way to the ranking match versus Letz Shake. Henry and Travis meet face-to-face after Henry kills Letz Shake before Travis, thus igniting a rivalry between the two.
He later challenges Travis to one final duel outside the Motel "NO MORE HEROES" after Travis becomes ranked first in the United Assassins Association. As their battle ensues, Henry reveals that he is both Travis' twin brother and Silvia Christel's husband of ten years. He also is seen to have a daughter named Jeane, a mysterious child who shares the same name as Travis' half-sister and cat, seen following the credits looking at a painting of Henry and Travis attacking each other in front of the Santa Destroy flag with her mother, Sylvia.
Though it was heavily implied in the real ending of No More Heroes that Henry and Travis had honorably killed each other, this was not the case as the game's sequel, No More Heroes 2: Desperate Struggle, reveals that Silvia interrupted the fight. Silvia also reveals that she and Henry divorced during the events between the games. In the sequel, he assists Travis in the final boss fight. However, he leaves after Batt turns into a giant form saying "It's not happening, brother. I can't be associated with that travesty. I mean, I got standards for fuck's sake!". He also kills the 2 assassins ranked after Ryuji and gets Travis to rank 5, despite the fact that he killed three assassins, althougth it is possible that two of them fought together or one of them was a challenger. Henry is also playable (without hacking) in No More Heroes 2: Desperate Struggle during the dream fight with Mimmy.