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Twenty years ealier, Tony Manetta, now a forty-year-old widower with an eleven-year-old son named Ally, came to Miami Beach from the Bronx with two buddies, Jerry Marks and Mendy, hoping to make a fortune. He now lives like a "big shot," but in truth is broke and in danger of losing the modest Garden of Eden Hotel, which he owns. After his banker, Abe Diamond, gives him forty-eight hours to come up with the money he owes in back payments, Tony calls his conservative older brother Mario in New York to ask for a $5,300 loan. Mario, a self-made small businessman who disdains his brother's lifestyle, refuses, but when Tony falsely tells him that his son Ally, whom the childless Mario and his wife Sophie adore, is sick, Sophie convinces her husband to fly to Miami. Tony's current girl friend, the free-spirited Shirl, would like him to let Ally live with Mario and Sophie, so that Tony would be able to enjoy a responsibility-free life with her. After Mario and Sophie arrive and find Ally well, Mario, who repeatedly calls his brother a "bum," offers to set him up in a five-and-dime store if he gets married and settles down. Seeing that Ally is afraid that he will be forced to live with Mario and Sophie, Tony agrees to meet a widow whom Sophie knows, Mrs. Eloise Rogers, who also lives in Miami. Tony then explains to Shirl that he is just trying to placate his brother and promises to take Shirl to dinner that night, then fly with her to Cuba for a romantic overnight stay. Shirl hopes that she can convince Tony to keep traveling with her after Cuba to places undetermined. When the kind and attractive Mrs. Rogers arrives at the hotel, Ally likes her immediately and prays that Tony will marry her, but when Mario boorishly explains his plan to set her and Tony up in a small business, then crudely asks if her deceased husband left her any money, Mrs. Rogers is so embarrassed, she walks out. Tony catches up with her and after a short spat, they buy groceries and drive to her apartment for dinner. Shirl sees them leave and cries in her room. As Mrs. Rogers prepares dinner, she talks about the accidental drowning deaths of her husband and son and admits that she is lonely. Tony, feeling she is too fine a person to "kid along," admits that he only agreed to meet her so that Mario would loan him money. To his surprise, Mrs. Rogers invites him to remain and says she is glad to be needed, even if it as only as a "stooge." When Tony returns to the hotel and says he had a wonderful time, Sophie and Ally are hopeful, but Mario, suspicious of his brother, refuses to give him any money until he opens the five-and-dime store. After Tony discovers that Shirl has left, he confronts Mario, telling him he refuses to become like him. Just as Mario is threatening to take Tony to court over custody of Ally, Tony is invited to a party at the Fontainebleau Hotel by his old pal Jerry, who is now a wealthy promoter. At the extravagant party, Tony tells Jerry about his dream of buying up decaying property and constructing a Florida Disneyland. Because Jerry acts as if he is interested in investing, Tony agrees to meet him in an hour at a dog track to discuss it further. To get enough money to act like a big shot, Tony quickly sells his Cadillac convertible for $500, and at the track, when Jerry and his vivacious secretary-girl friend Dorine each bet $500 on a dog, Tony matches their bets. His dog wins, and when he learns that it paid enough for him to make up his back payments on the hotel, he exuberantly calls Ally. Mario, upon hearing the news, is distraught that Tony would get the money from someone other than his own brother. Later, when Tony sees that a dog named "Lucky Ally" is entered in the next race and Jerry suggests they let their bets ride, Tony agrees and prays for the dog to win. The dog loses, and Jerry, unaffected by the loss, is about to leave when Tony grabs him and asks about their deal. Jerry reminds Tony "never try to promote a promoter" and gives him a wad of bills, which Tony throws in his face. After one of Jerry's thugs punches Tony in the stomach, doubling him over, a distraught Tony returns to the hotel where Ally has assembled his friends, including Mrs. Rogers, to celebrate. Admitting he is a bum, Tony asks Mario to take Ally because he does not want his son to become like him. Although Mario now feels sorry for Tony and offers him money to keep the hotel, Tony refuses it. Hoping to convince Ally to go with Mario, he lashes out at the boy, pretending to blame him for his loss of the hotel, his money and Shirl. When this does not work, Tony slaps Ally and walks off to the beach. The next day, Tony watches from the oceanfront as Ally, Mario and Sophie say goodbye to Mrs. Rogers and get into a cab. A still distraught Ally runs back to his father, however, and they fall into the surf, embracing and crying. Mrs. Rogers then invites them to a meal at her place, and Mario and Sophie, deciding to take their first vacation in years, follow them as they run playfully along the beach.