Educated at Paterson High School, Milholland was aided by William Walter Phelps and attended New York University.

[2][3] After two years, he dropped out and became a journalist, working for the Ticonderoga, New York Sentinel, which he eventually bought.

Milholland subsequently sold the paper and was employed by the New York Tribune, where he reached chief editorial writer.

Reid was nominated for vice president, in large part through the work of Milholland, for which he was named assistant secretary of the National Republican Party.

An antiexpansionist, Milholland soon moved to London, where he founded the International Union Club, which supported the Boers.

[4] He used the large amounts of money he earned to fund several civil-rights activists, first Booker T. Washington, and later W. E. B.