Tip on a Dead Jockey is a 1957 film drama starring Robert Taylor . It is based on the The New Yorker 1954 short story by Irwin Shaw.
Phyllis Tredman is shocked when husband Lloyd, a decorated Korean War pilot, sends word to her after his discharge from military service requesting a divorce. She tracks him down in Madrid, Spain, where it turns out Lloyd is drinking and gambling heavily. He is tormented by having ordered so many Air Force pilots to their death on dangerous missions. He also is strangely attracted to Paquita, the wife of his friend and fellow pilot Jimmy Heldon.
A mysterious man named Bert Smith, aware that Lloyd is down on his luck, offers him $25,000 to do something illegal and dangerous—transport currency from Cairo to Madrid, dropping the box of cash in mid-air. Lloyd has wagered his last $1,000 on a horse race. He says if the horse wins, he won't need Smith's offer, but the race ends tragically with the jockey killed. Lloyd suspects foul play.
Robert Taylor as Lloyd Tredman
Dorothy Malone as Phyllis Tredman
Marcel Dalio as Toto del Aro
Martin Gabel as Bert Smith
Gia Scala as Paquita Heldon
Jack Lord as Jimmy Heldon
Hayden Rorke as J. R. Nichols
Joyce Jameson as Sue Fan Finley