Rip Van Winkle was a First Lieutenant for Millennium, nicknamed the Huntress. She, like future officers the Major, the Doctor and the Captain, was first chronologically seen in the Order 666 camp in Warsaw, during the events of Hellsing: The Dawn. She, an Untersturmfuhrer, was first seen as a pathetic figure, farsighted, incapable of realizing that Alucard, in a shape similar to a small girl, is the enemy, until it is too late and his coffin knocks her out. She was one of the few survivors of the destruction of the camp. Later, she joined Millennium, eventually making it to the elite Werwolf team, though she apparently retained a phobia of Alucard, referring to him as the Black Huntsman Zamiel, in a reference to her favorite opera, Die Freischutz. She also was prone to liken herself to Die Freischutz's main character, a huntsman named Kaspar, who is eventually killed and draged to Hell by Zamiel.
She was chosen to lead a Millennium strike team to take possession and defend Millennium's propriety of a British VTOL warship, the Eagle, surrendered by traitorous, vampirized Englishmen. While she did so, she also executed another of her orders: to eliminate the traitors, stating Millennium wasn't interested in their services. She then proceeded to rename the Eagle as the Alder and declare it a Nazi warship under the service of Millennium, painting a massive swastika in red paint in the main deck. Her defensive task was aided by her old-fashioned musket, capable of firing magic warheads capable of penetrating heavy armor and repeteadly hit an object, returning and changing paths several times in midair. She used this ability to bring down missiles and choppers alike, effectively defending the newly-christened Alder.
Hellsing, deciding not to allow such a powerful ship under foreign control so near England landmass, sent their greatest vampire agent, Alucard, to deal with the threat of Van Winkle. Equipped with an extremely fast spy jet, Alucard rammed the jet into the Alder itself at the plane's top speed, so even if the terrified Van Winkle or the ship's defenses managed to hit him, he still would hit the ship. Despite the Millennium soldiers' attempts, Alucard reemerged and destroyed them all before focusing on Van Winkle. She then attempted to force him off the deck and into the water by using another magic bullet, but just before she triumphed, Alucard caught the bullet in his mouth. He then executed Van Winkle upon her own musket and drain her blood in a very slow pace, turning Van Winkle into his familiar. Schrodinger appeared and informed Van Winkle the Major had decided not to fry her through her chip and instead ordered the entire Millennium crew to Heil her, bidding her "Auf Wiedersen" before the invasion fleet reached for England. The plan was, since Alucard could not pass through the ocean without external means of locomotion such as a boat or a plane, he would remain stranded upon the reclaimed Eagle until it was too late. This plan failed, and Alucard made it to land safely.
She would later reappear as Alucard summoned his strongest familiars, at first partly merged with fellow Millennium lieutenant Tubalcain Alhambra. They both used their special abilities to shoot down Enrico Maxwell's helicopter and destroy the Millennium invasion, until they were killed by the holy fire extending from the gaping wound Paladin Alexander Anderson inflicted upon Alucard with a Nail of Helena-enhanced silver bayonet.