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When millionaire philanthropist Homer Van Dine Harmon sends his pal Poggle to collect the rent from the residents of his East Side tenements, his emissary is attacked by a gang of kids and run out of the neighborhood. Believing that he can do a better job collecting the money, Homer accompanies Poggle back to the East Side to show him how to deal with the "hoodlums and roughnecks." No sooner does Homer drive into the neighborhood, however, than his car is pelted with debris, and he becomes involved in a street fight. During the attack, Homer grabs one of the young hoodlums, a boy named Clipper, and while trying to scold him, Homer is socked by the orphaned boy's older sister and sole guardian, Margie, who has come to her brother's defense. Homer instantly falls in love with her. Following Clipper's trial at the Children's Court, in which Homer, during his testimony, is distracted by Margie's presence, he sees Clipper slap his sister and intervenes on Margie's behalf. He protects Margie and then offers to take Clipper out of the gutter and help him stay out of trouble. His plan, to convert one of his tenements into the Harmony Hall Boys' Club, a gymnasium for East Side kids, is met with resistance by Clipper and the adult leader of the kids' street gang, Butch, who uses Clipper to help him commit various crimes. Though Clipper threatens to punch any kid who goes to Homer's gymnasium, Margie succeeds in convincing the boys to take advantage of Homer's generous gift, and the philanthropist kisses her out of gratitude for her accomplishment. To keep the boys entertained, Margie suggests a boxing match between Poggle and Homer, both of whom are inexperienced fighters. A match between East Side champion fighter Mulvaney and Homer results, in which Homer pays Mulvaney to let him win. However, when Butch pays Mulvaney to give Homer a real fight, the millionaire is double-crossed and knocked out. Later, after Clipper aids Butch in a stickup, he returns home to find that Homer and Margie have prepared a birthday celebration for him. Clipper is contemptuous of their effort and, after stealing Homer's timepiece, leaves the apartment. Homer and Margie are soon visited by a policeman who caught Clipper trying to hawk Homer's timepiece at a nearby pawnshop. In a noble gesture, Homer tells the officer that he gave the boy his watch as a gift, thus saving Clipper from prosecution. Homer, who finds that he has difficulty proposing marriage to Margie, turns to Poggle for help, and Poggle suggests that he record his proposal on a phonograph and then play the record at their next meeting. With Poggle's assistance, Homer reads off titles from popular love songs into a microphone and then plays the recording for Margie in his living room. Margie agrees to marry Homer only if he succeeds in keeping Clipper away from the hoodlums. Meanwhile, Butch concocts a plan to kill Homer by having Clipper load real bullets in the gun that is to be used as a prop in an upcoming Harmony Hall stage production. But during the play, Clipper, stricken by his conscience, is unable to pull the trigger. Butch then forces Clipper to put on his "blonde bandit" disguise and go to Homer's to commit a new crime. However, Homer, in costume for the play, is mistaken for Clipper and taken to his own home to commit Butch's crime. Back at Harmony Hall, Clipper confesses his misdeeds to Margie and then, with the help of his friends, rescues Homer from Butch. Having succeeded in putting the thugs out of commission and reforming Clipper, Homer and Margie embrace.