When his father handled the bankruptcy of the Union Pacific Railroad Skip Dundy was appointed master in charge of that $20 million case, showing his aptitude for financial matters.

Their static walk-through setup made them not as popular as an elaborate moving diorama ride called "Darkness and Dawn" put together by a rival showman, Frederic Thompson, and Dundy lost money on the fair.

At the planning sessions for the 1901 Pan-American Exposition in Buffalo, New York Dundy proposed his own pirated version of "Darkness and Dawn" and used his business skills to outmaneuver Thompson in getting the midway concession.

Since there was a 3-year gap until the next worlds fair in St. Louis, Thompson and Dundy were convinced by George C. Tilyou to move "A Trip to the Moon" and the "Giant See-Saw" to his seaside Steeplechase Park on Coney Island in Brooklyn, New York.

But things changed for the partnership in 1906 when Thompson married stage and silent-screen actress Mabel Taliaferro and put all his efforts into building her career, leaving the work of running their various entertainment venues to Dundy.