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Newly released from a Kentucky prison, "Colonel" John Appleby, a cardsharp, heads to Chicago under the supervision of his niece, Leonora, a nightclub singer. Afraid that he might be sent back to prison, she insists that he give up his criminal ways and follow her on the straight-and-narrow path. On the train to Chicago, John and Lee meet Bob Wendell, the lead investigator for the Illinois State Attorney's office, which is looking into gambling in Chicago, and the three become reacquainted when Bob raids the Skyline Club where Lee works. However, the club's owner, racketeer Marty Martin, has been warned about the raid by Bob's sister Gloria, to whom he was once engaged and is now blackmailing, and quickly turns the backroom poker game into a chess club. Later, at a music store, a smittened Bob tries to convince Lee to quit the Skyline, but she refuses. Told by Gloria how Bob feels about Lee, their aunt Butch has Lee abducted and brought to the Wendell home for dinner. Butch's millions attract the attentions of John, and the wealthy widow soon falls under his romantic spell. The next morning, John shows his niece a deck of marked cards he had taken from the card room at the Skyline, which prove Marty is a cheat, but Lee still refuses to let her uncle practice his trade. Later, Bob and Lee attempt a romantic rendezvous in the park, only to be interrupted by a philosophical tramp. Bob and John then ask each other's permission to court Lee and Butch, respectively. Their plans are disrupted, however, when Crane, a Kentucky policeman, recognizes John. The cardsharp promises Crane he will leave town if Crane agrees not to tell Bob about his past. Meanwhile, after raiding Marty's country home and confiscating his incriminating financial records, Bob receives a note from the racketeer, threatening to go public with a scandalous photograph of Gloria if he is prosecuted. After meeting Gloria at the train station, John goes to the Skyline in an attempt to win the negative away from Marty in a game of poker. Despite Bob's arrival, the game continues, with Marty betting his "lucky rabbit's foot"--a cigarette holder containing the negative--against Lee's promise to go away with him. John wins the hand, along with Butch, who offers to buy the Skyline for him. Bob also unites with Lee and admits that he knew all about her uncle's past from the beginning.