[1][2][3][4] Cudahy dropped out of school at age 14 and found a job working at Layton and Plankinton, Milwaukee, an area meat packing plant.

By 1869, Cudahy was a manager in charge of the packing house at Plankinton, Armour and Company, which had been established in Milwaukee in 1852.

[1][5] With the help of his brothers Edward and Patrick, he established the Cudahy Packing Company in South Omaha, Nebraska in 1890.

He also owned a home in Hubbard's Annex on the island in the late 19th century, which he later sold to his brother Edward.

[citation needed] Cudahy handpicked renowned architect Frederick Wainwright Perkins to fulfill his visions of a West Bluff mansion.