Rip Van Winkle

One of Millennium's top soldiers and a member of the Werewolf special forces, van Winkle commands her troops to steal a VTOL carrier called the Eagle from the British. Along with Zorin Blitz and Schrödinger, she briefly makes a cameo in a flashback during Hellsing III, and also during the ending credits. She makes her full appearance in OVA IV.

Rip uses a long-barreled flintlock musket that fires magic bullets which "punish all without distinction," tracking targets of their own accord, and which are seemingly armor-piercing (destroying helicopters, fighter jets and missiles with ease). These magic bullets are even able to change their trajectories in mid-flight and repeatedly pepper a target before expiring. Rip seems to have a limited amount of these bullets, as she only uses one at a time. In fact, she uses only five on-screen before death throughout the entire series and only one directly against Alucard (so far: she might use them again during The Dawn.) It's possible that this could be due to the fact that she has to go through the slow process of manually reloading the musket after each shot, forcing her to rely on taking out her all of her targets with a single, decisive shot during engagements. She does not appear to have any other powers beyond this however.

She also enjoys singing operas, especially Der Freischütz, and she often compares herself to the character Kaspar from that opera. The Major even notes that she is very much like Kaspar (and also likens Alucard to Zamiel, the antagonist of that opera and representative of the devil). Additionally similar bullets, that never miss their target, are used by Kaspar. The Major at one point tells Rip the end of Der Freschütz and says she'll suffer a similar fate. The exact quote is "First Lieutenant Rip Van Winkle, do you know how Der Freischütz ends? Kaspar, having trifled with the Black Huntsman Zamiel, is whisked away to hell for his sins. His corpse is then thrown into a ravine to be eaten by wolves. Prepare yourself, First Lieutenant, for now, Zamiel comes to collect you."

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.

Alucard instills a great deal of fear in Rip as he approaches, and inevitably kills her, despite her last ditch effort to force him over the edge of the Eagle's deck with a magic bullet. Alucard stakes her through the chest just left of her heart with her own gun, after being repeteadly peppered by the bullet and then literally catching it in his mouth. He then drinks her blood in the climax to Volume 5 of the manga before using his shadows to devour her body, killing her and making her his familiar.

Rip is rather childish compared to most characters in the series; while onboard the Eagle, she counts down the time to Millennium's attack with a child's alarm clock with a cartoon face on it. She also has a freckled face, characteristic of schoolgirls, and in 1944 wears her hair in pigtails which further emphasises that point. When she senses Alucard's approach, she starts shaking, and at one point retreats within the ship sobbing. This, and the brutal manner of her death, makes her one of the more sympathetic villains.

Ironically, The Major would not permit the Doctor to fry her through the chips, and in fact, in a rare gesture of "generosity,"requests other members of Millennium to Heil her, bidding her "Auf Wiedersehen." ("Sayonara" in the Japanese version) Her mission was to effectively trap Alucard on the Eagle because he cannot cross water without the aid of some form of external transport such as a plane or ship. By using the Eagle as a decoy, Millennium isolates Alucard in the middle of the ocean while the rest of Millennium makes its landing operation; to boost the morale of his army to a fever point, the Major glorifies Van Winkle's death (even promising her through the radio they would again meet in Valhalla) so hers will be the first death of the operation, thus priming the army for the destruction of London. Unfortunately for Millennium, Alucard takes control of the ship and manages to return to coastline, though the Major himself seems to be anticipating this.

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. This scene was not published in Young King OURs, but was added to volume 9.

In the most recent chapter of The Dawn, Rip also makes an appearance as a young, farsighted soldier, encountering Alucard after his initial defeat by the Captain and while he was smoking with his coffin. She appears in full uniform, wearing her hair in two braided pigtails, and bears the rank of Untersturmführer. The glasses she wears (which are not actually hers, but were mixed up in the confusion) make it difficult for her to focus properly, and Alucard spends some time trying to make her understand who he is and why he's in the building. Finally, realizing that he is an enemy, Rip tries to shoot Alucard, but is knocked unconscious by his sentient coffin in an amusing way: being Judo chopped and kicked across the hall.

Since The Dawn is currently incomplete, it is often debated among fans that she was turned into a vampire and given magic bullets by Alucard himself. This would seem to explain why they were familiar with one another in volume 5, and it would also make the comparison to Der Freischütz that much more literal. However, it is unlikely Alucard was indeed her sire, seeing the immense difference in sheer battle power seen between Rip and Alucard's true fledging, the former policewoman Seras Victoria.