Maskelyne was born in 1863 to noted stage magician, J.N. Maskelyne. Following his father's death, he assumed control of Maskelyne's Ltd. He continued his father's work at the Egyptian Hall in London. He also worked in the area of wireless telegraphy and was a competitor and public detractor of Guglielmo Marconi in the early days of radio (wireless). On one occasion he hacked into Marconi's demonstration of wireless telegraphy, and broadcast his own message, hoping to make Marconi's claims of "secure and private communication" appear foolish.
Maskelyne was the father of Jasper Maskelyne, who continued the family tradition of professional magic.