Handy taught school at Dames Quarter, in
Somerset County, Maryland, and in 1881, at the age of 19, was selected to be principal of the high school at
Smyrna, Delaware. By 1887 he was superintendent of all the public schools in
Kent County, Delaware, and by 1890 he had been hired as principal of Old Newark Academy, in
Newark, Delaware. Meanwhile, he was studying the law with John R. Nicholson of
Dover, Delaware, and frequently speaking at teacher's training schools in the region. Retiring from teaching in 1892, he became an editorial writer for the
Wilmington Every Evening newspaper. He also studied law, was admitted to the bar in 1899, and began the practice of law in Delaware. With his retirement from teaching he took a more active role in politics, becoming chairman of the Democratic State Committee from 1892 until 1896. He sought the 1894 Democratic nomination for U.S. Representative, but lost to
Samuel Bancroft, who himself lost in the election. Handy was elected to the U.S. House of Representatives in 1896, defeating incumbent Republican U.S. Representative
Jonathan S. Willis. During this term, he served in the Democratic minority in the 55th Congress. Seeking reelection in 1898, he lost to Republican
John H. Hoffecker, a Smyrna businessman and relative of his wife. In all he served from March 4, 1897, until March 3, 1899, during the administration of U.S. President
William McKinley. Subsequently, Handy remained active in politics, attending the Democratic National Conventions of 1900, 1904, and 1908, and losing an election for state Attorney General in 1904. He ran for U.S. Representative one more time, in 1908, but lost to Republican
William H. Heald. ==Death and legacy==