First Lieutenant Rip van Winkle

First Lieutenant Rip van Winkle (リップヴァーン・ウィンクル中尉 Rippuvān Winkuru Obersturmführer?) is one Millennium's top soldiers and a member of the Werewolf special forces. While a youthful-looking freckled vampire with glasses, van Winkle is actually 70 years old by the time of the series. She also seems to be childish and bipolar with a passion for Der Freischütz as she often sings songs from the opera while comparing herself to its lead character Caspar. This also plays in her use of a long-barreled flintlock musket that fires magic bullets which "punish all without distinction," tracking targets of their own accord by changing trajectories in mid-flight, seemingly armor-piercing and repeatedly pepper a target before expiring. van Winkle seems to have a limited amount of these bullets as she only uses one at a time. Her prototype was in Coyote.

As revealed in Hellsing: The Dawn, while bearing the rank of Junior Warrant Officer, van Winkle encountered Alucard half a century ago after his initial defeat by the Captain and while he was smoking with his sentient coffin. Though she eventually recognized Alucard as an enemy, van Winkle is easily dispatched and since developed a phobia after the Major compared Alucard to Zamiel, the demon that eventually drags Caspar to Hell.

During the main storyline, van Winkle is assigned by the Major to take the VTOL carrier Eagle as a distraction for Alucard in what is later revealed to be the Major's attempt to strand the vampire in the middle of the Alantic Ocean so Millenium can begin its invasion of London. After slaughtering the ship's vice-captain and his associates, switched sides and orchestrated the mutiny as vampires, van Winkle subsequently renames British ship as Adler while painting a swastika in blood on the main deck while the members of the Letztes Battalion awaken. Though van Winkle is able to snipe down any approaching planes, Alucard uses a remodeled SR-71 Reconnaissance Jet to reach the ship and slaughter the entire Letzte Battalion. Despite a last ditched effort to kill Alucard, with the Major telling the Doctor to let her die a hunter's death instead of incinerating her as a rare gesture of "generosity", van Winkle is consumed in the vampire's shadows and becomes his familiar.

Rip later shows up as a familiar after Alucard releases his zero restriction, merged with Tubalcain Alhambra. After helping shoot down Maxwell's helicopter and attacking Anderson, she is destroyed in a massive fire along with all the other familiars likely killing her for good. This scene was not published in Young King OURs, but was added to volume 9. In several scenes she is also seen with an umbrella, which could be a reference to the practice of World War II German snipers to use umbrellas with camouflage foliage woven between the arms as light, adaptable and mobile personal camouflage.