O’Sullivan was born in Listowel in 1874. He developed an early interest in the GAA and in 1893 at the age of nineteen became secretary of the newly formed Listowel Temperance Football Team. In 1899 he became secretary of the Listowel GAA. He was appointed county secretary after the Kerry board was reformed in 1900. In 1903 he was appointed president of the Munster GAA council. He continued as secretary of the Kerry board until he moved to Dublin to write for the Freeman’s Journal in 1907. O’Sullivan held a number of positions for that newspaper, including a spell as parliamentary correspondent in London from 1916, until its demise in 1924. His Story of the GAA (1916) was the first ever history of the association.