City of Shadows

Racketeers Toni Finetti and Angelo Di Bruno have been pressuring the owner of Billy's Steakhouse to buy their expensive slot machines. The machines currently at the steakhouse are outmoded and dilapidated, but provide the livelihood of Big Tim Channing, a softhearted, small-time racketeer. In addition to the threat of losing business, Tim is troubled by a rash of "slug passing," or gamblers playing slots with fake coins. Kink, the steakhouse bartender and Tim's good friend, catches impudent, twelve-year-old newsboy Dan Mason illegally playing the slots and winning the jackpot. When Kink discovers that the young con artist has a sack of slugs, Dan, without apology, admits that he has organized the newsboys to pass them. After chastising Tim for not thinking of it himself, Dan suggests that Tim could run his competitors out of business by paying the newsboys to pass slugs in Finetti and Di Bruno's slots. Despite Dan's rude manner, Tim warms to the boy, especially after learning that, like himself, Dan is an orphan. Ten years later, a nattily dressed Tim runs a syndicate and counts Finetti, Di Bruno, Kink and disbarred attorney Davis among his employees. A father-son relationship has developed between Dan and Tim. Looking forward to the day when Dan will become the syndicate's attorney, Tim is sending the young man through law school. Already the studious Dan has found legal loopholes that have kept Tim and his subordinates out of jail. Most recently, Dan has discovered a forgotten 1867 statute, which was invoked to dismiss racketeering charges against Tim. The judge and District Attorney Hunt are mystified by Tim's success in eluding conviction. After losing the high profile case against Tim, Hunt and his men prepare to extradite Finetti for an out-of-state murder charge. At school, Dan finagles an invitation from his classmate, Roy Fellows, to meet his sister Fern at his parents' home in the country. Dan's real motive for going to the country is to peruse the collection of rare legal tomes owned by Roy's father, the retired Judge Fellows, for a way to block charges against Finetti. The Fellowses like Dan, although they are astonished when he reads law books instead of romancing Fern. Eventually, Fern convinces him to go to a dance, where Tim and his men find him when developments in Finetti's case need his attention. Using Judge Fellows' books, Dan has devised a strategy to counteract charges against Finetti and passes the information to Tim. Di Bruno, who still holds a grudge against Dan for passing slugs, makes a pass at Fern, prompting Dan to fight him and almost choke him to death. Later, Dan, who has fallen in love with Fern, confesses his criminal background and asks her to give him time to turn his life around. After Dan graduates, he forces the proud Tim into starting a legitimate business. The insurance company that Dan establishes, Twentieth Century Security, offers its clients additional protection in the form of a corps of guards formed from ex-servicemen and retired policemen. As Dan has found a niche with a public that is disenchanted with ineffectual police protection, his company is successful and Dan is awarded many civic honors. However, he is unaware that Finetti and Di Bruno have forced Tim to run an illegitimate protection racket alongside the straight business. Noticing that only non-participating businesses are reporting crimes, Hunt sends an undercover agent, Phil Jurgins, to check out the company. Phil is hired by Dan as a public relations specialist and supplies Dan's secretary, Linda Fairaday, with pencils bearing his PR company logo. At Hunt's orders, Phil also interviews the Fellows family about Dan, but receives only glowing comments. Believing he has nothing to hide, Dan assumes that the investigation is routine. From a fellow racketeer in the wastepaper collection business, Tim learns that Twentieth Century trash has been marked with some kind of luminous powder, which identifies it when a special light is shone on it. He then realizes that either the district attorney or federal agents have taken an interest in collecting the company's papers. Guessing that Phil is an agent and that the pencils he gave her contain a special lead, Fairaday informs Finetti, who has secretly placed her in Dan's office to keep an eye on him. Believing the business is going well, Dan plans to retire Tim soon in grand style and marry Fern. However, when Phil is slain by Finetti and Di Bruno's thugs, Dan learns that Tim has not been playing straight. Exasperated, he throws his marriage license at Tim, saying that he had been trying to keep Tim out of the electric chair. Dan is making arrangements to dissolve the company, as well as his engagement, when Tim and Fern show up arrive at his office. Tim has negotiated to meet with Hunt, after Dan and Fern are married, and plans to confess all. Overhearing the plans, the eavesdropping Fairaday reports them to Finetti. After Tim acts as best man at Dan and Fern's private ceremony, he takes them on a honeymoon to his remote mountain cabin, which is accessed by ski lift. After watching Dan carry Fern across the threshhold, the fatherly Tim begins his journey back to the city. Meanwhile, Finetti and Di Bruni have tortured Kink into revealing Tim's whereabouts and go to the ski lift where they kill the caretaker. On the ski lift, they meet Tim, who is on his way down the mountain, and shoot him. Tim falls from the ski lift, but follows the thugs, and shoots and kills them. He is near death when Fern and Dan find him. Before dying, he tells Dan to remember: "When you play with slugs, you get slugged on another day."