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While working as a teacher in Paterson, New Jersey, Holland designed his first submarine. The Fenian Brotherhood, an Irish independence movement to which Holland's brother belonged, financed his work as a way to challenge British control of the seas. With Fenian funding, he built three submarines, Holland I, II (named Fenian Ram), and III. In November 1883, Fenians unhappy with Holland's slow progress stole the Fenian Ram. The submarine, however, was never operated successfully. Holland began working in 1884 for U.S. Army Lieutenant Edmund Zalinski's Pneumatic Gun Company, which financed Holland IV, also known as the Zalinski Boat, in 1885. At this time Holland met U.S. Navy Lieutenant William W. Kimball, who began lobbying the Navy Department for submarines.
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Holland entered and won the Navy's next submarine competition in 1893, with Holland V the Plunger. Holland modified this design and the result, Holland VI, was launched on May 17, 1897. She began sea trials on March 11, 1898. Holland sent the Navy the specifications for Holland VI in late 1899, and Holland's supporters mounted a strong lobbying campaign. On April 11, 1900, the Navy purchased Holland VI. The submarine was commissioned in the Navy as USS Holland (SS-1) on October 12, 1900.