Allen was born in Warren County, Pennsylvania to John and Rebecca Elizabeth (Goodwin) Allen. His family moved to Kansas in 1870, where they settled in Clay County.

Before becoming active in politics, Allen acquired ownership of newspapers throughout Kansas, beginning with the Manhattan Nationalist in Manhattan, Kansas in 1894. Generally forward-looking in his outlook, he hired Frank Lloyd Wright to design his home in Wichita, Kansas. Allen's home is the only residence designed by Wright in Kansas.

Allen was in France with William Allen White inspecting the facilities provided to Kansas soldiers of the American Expeditionary Force during World War I when his party nominated him for the office of governor. During the campaign in 1918, Allen never spent any of his own money and learned about his nomination from a Paris newspaper.

Allen expressed some admiration for Benito Mussolini's policies in the 1920s and pushed through a similar industrial court provision. When publisher William Allen White objected, he was arrested in a free speech battle. White won the 1923 Pulitzer Prize for his editorial "To an Anxious Friend," published July 27, 1922 opposing the law.

Allen died in 1950 following a cerebral thrombosis in Wichita, Kansas. He is buried at the Maple Grove Cemetery in Wichita, Kansas. Allen was posthumously inducted into the Kansas Newspaper Hall of Fame two years later.