Upon checking came up with more information and there is definitely a connection. One of my Cleary relatives informed me she has a picture of John McGeehan taken in Chicago in his later years. He was also definitely in Wisconsin because he was the godfather of Bernadine Cleary, born in 1903, who was the daughter of James McGeehan and Elizabeth Cleary.
The family of James Edward Cleary (b. 1861), whose daughter Bernadine (b. 1903) had John McGeehan as a godfather, settled in Ashland, Wisconsin. James Edward Cleary was the brother-in-law of John McGeehan.