Harold Lincoln Gray (January 20, 1894 – May 9, 1968) was an American cartoonist, best known as the creator of the newspaper comic strip Little Orphan Annie. Early life Harold Gray was born in Kankakee, Illinois on January 20, 1894, to Estella Mary () and Ira Lincoln Gray, a farmer. Both parents died before he finished high school in 1912 in West Lafayette, Indiana, where the family had moved. In 1913, he got his first newspaper job at a Lafayette daily. He could trace his American ancestry back to 17th-century settlers. He grew up on farms in Illinois and Indiana, and worked in construction to pay his college tuition at Purdue University. He graduated with a degree in engineering by 1917. Gray approached cartoonist John T. McCutcheon for advice on breaking into the cartooning field. He could not immediately get cartooning work, but McCutcheon's influence got him work as a reporter for the Chicago Tribune before he enlisted in the military for World War I, where he was a bayonet instructor for six months. Discharged from the military, he returned to the Chicago Tribune and stayed until 1919 when he left to freelance in commercial art. In 1923, while residing in Lombard, Illinois, he became a Freemason. Comic strips From 1921 to 1924, he did the lettering for Sidney Smith's The Gumps. After he came up with a strip idea in 1924 for Little Orphan Otto, the title was altered by Chicago Tribune editor Joseph Medill Patterson to Little Orphan Annie, launched August 5, 1924. Gray's first wife, Doris C. Platt, died in late 1925. He married Winifred Frost in 1929, and the couple moved to Greens Farms, Connecticut, spending winters in La Jolla, California. By the 1930s, Little Orphan Annie had evolved from a crudely drawn melodrama to a crisply rendered atmospheric story with novelistic plot threads. The dialogue consisted mainly of meditations on Gray's own deeply conservative political philosophy. Gray made no secret of his dislike for the New Deal ways of President Franklin Roosevelt and would often decry unions and other things he saw as impediments to the hard-working American way of life. Critic Jeet Heer, who did his thesis on Gray and wrote introductions to IDW's Little Orphan Annie collections, commented: Gray wasn't really a conservative in the 1920s: he was more of a general populist, hostile to loan sharks and speculators while celebrating hard working