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Based on a story by Damon Runyon, Hold 'Em Yale is also more than a little beholden to O. Henry's Ransom of Red Chief. Spoiled-rotten heiress Clarice Van Cleve (Patricia Ellis) is enticed to New York by fortune-hunter Gigolo Georgie (Cesar Romero), who dumps her in the apartment owned by Runyonesque hoodlums Sunshine Joe (William Frawley), Liverlips (Andy Devine), Sam the Goniff (Warren Hymer) and Benny Southstreet (George E. Stone). Plotting to hold Clarice for ransom, the four hooligans figure that this "dame" will be easy to handle. Boy, are they wrong! Like the proverbial babysitter from hell, the temperamental Clarice is soon ruling the roost in the foursome's hideout. The beleaguered crooks offer to ship the girl back to her father, Mr. Van Cleve (George Barbier), only to find out that he won't take her back -- not even for free! In desperation, the four hoods try to marry Clarice off to college football-hero Hector Wilmot (Buster Crabbe), and to that end they try their best (?) to "fix" the annual Yale-Harvard game so that Hector will prove worthy of the hoydenish heroine -- which, as it turns out, was Mr. Van Cleve's plan all along.