Whalen was a historian and an expert on the 20th century. In 2364, Whalen was serving aboard the Galaxy-class starship USS Enterprise-D when Captain Jean-Luc Picard invited him to participate in a holographic adaptation of The Big Good-Bye. The holodeck program was a Dixon Hill story, set in 1941 San Francisco. Whalen was familiar with The Black Orchid, another novel in which Dixon Hill was also the main character. Freed from the holodeck, the officers exited, taking Whalen with them. (TNG: "The Big Goodbye" )