Ribs Mocco, the last free man of Big Boy’s grand organization sends for master pickpocket and slight of hand expert Stooge Viller. His organization is willing to pay Stooge $10,000 if he gets rid of Dick Tracy by non violent means. Stooge takes the job, observes Tracy and comes up with a plan to frame Tracy. Stooge plants counterfeit money in Tracy’s pocket and also hidden several places in his house. Tracy, who is planning a wedding with Tess is out shopping and uses the counterfeit money to make several purchases and Stooge makes sure each of the shopkeepers report the crime to the police. When Chief Brandon finds counterfeit money in Tracy’s pockets he’s fired, and later when additional money is found hidden in Tracy’s apartment Tess calls off the wedding.Tracy and Junior stick together and try to investigate the setup. Junior begins to notice Stooge time and again but usually when Tracy is not looking. Stooge and Ribs rejoice at the downfall of the great detective and Stooge decides to try and woo his girl Tess. Ribs argues this is a bad idea but Stooge doesn’t listen and soon Stooge sets up situations to get in good graces with Tess and take her out to the Ritz. Meanwhile, Tracy has reached a dead end and he and Junior plan to visit Tracy’s uncle who has a ranch in Elmina, Kansas.Stooge finally makes a mistake, writing a message to his cohorts out east, bragging about his accomplishments. When Stooge visits Tess’s apartment she finds the message in his coat pocket. When she goes to call the police Stooge shoots her in the shoulder and runs for it. Ribs and Stooge both decide to skip town but Stooge runs into Junior and Tracy at the train station. Initially Tracy doesn’t believe Junior’s insistence that Stooge is no good, but when Stooge hits him for pestering Tracy gets involved and the two brawl it out. Stooge is knocked unconscious by Tracy on the train tracks and police arrive. Tess, who is in the hospital has informed Patton and Brandon of the situation and Stooge is arrested and Tracy reinstated. Sadly the Tess/Tracy relationship has cooled and the wedding is put on hold.
Steve the Tramp travels west into Colorado and takes on a job as a hired hand with a blind ranch owner named Hank Steele who lives alone except for his cook Della. Hank tells Steve he was once a gold prospector who struck it rich but went blind from a dynamite blast. His wife ran away with a wandering traveller and she took her three month old boy with her. That boy would be nine years old now and Hank admits he would pay a $5,000 reward to have the boy back. Steve figures he can pose Junior as the old man’s long lost son and cash in on the reward.Back in the city, Tracy is out of town and Junior is staying with Tess. Steve slips back in to town, kidnaps the boy and the two hop a train heading to Colorado. Tracy returns and immediatly deduces Steve has kidnapped Junior again and he puts out a flash message across the country with the description of Steve and Junior. Junior does his best to help, writing a letter back to Tracy but Steve catches him and holds a mail truck to recover the letter.Still heading west, Steve runs into an old aquaintance, Dippy McDoogun. The two men steal a railroad pump car and make good time for awhile before their car is caught on a bridge and hit by a train. Dippy seems to drown in the river below the bridge but Steve and Junior crawl out, stopping at an abandoned grain elevator. Tracy almost rescues Junior there but Steve uses a trapdoor to drop him into a pit and he runs with the boy, hijacking a farm truck. Steve fires his weapon back towards Tracy but accidently shoots the driver and the vehicle crashes but the Tramp again gets away with Junior.Finding a letter Steve wrote to Hank Steele, Tracy skips ahead of the Tramp and tells Hank that Steve is coming but that the boy is not his son. He then hides himself away to catch Steve when he arrives. Steve and Junior arrive and Hank greets the two, and identifies Junior by the L shaped scar on the side of his head and proclaims Junior is indeed his son Jackie and that Steve hasn’t done a wrong in recovering his son.Tracy tells Steve he is still going to jail for the murder of a mail man and Steve in a private moment tricks the cook Della into believing that Tracy is a fake cop. Della takes a shot at Tracy with a rifle and Tracy returns fire, wounding Della while Steve ran off and jumped off a high cliff side. Tracy and Hank bring Della into the house, putting her in bed and Della tells them she knew all along and was trying to shoot Steve. Della dies soon after from her wounds. Although it pains both him and the boy, Tracy leaves Junior behind with his father Hank.At the bottom of the cliff, Steve has survived the fall but is badly hurt and a couple of wandering ruffians patch him up thinking he might have a lead on some money. Soon the men decide the Tramp is not worth it and they leave him in a blanket on the side of the road where he is found by a traveller who takes him to a doctor. When Tracy reads about the wounded man found on the road, he returns and arrests Steve. The famous criminal lawyer J. Peter Twillbrain chooses to defend Steve after he hears the big man has $5,000 in reward money but his defense fails and the judge senteces Steve to life in prison.
Stooge Viller and Steve the Tramp meet in the penitentiary and quickly bond over their hatred of Dick Tracy and the boy Junior. Stooge has made several failed attempts to escape prison where he is serving a 10 year stint for counterfeiting and Steve is serving a life sentence for murder. The two participate in a variety of jail house jobs on the lookout for ways to escape when notice a new water main tunnelling under one of the prison walls. The two skip a dinner bell a haul naptha (an explosive) from the soap factory to the wall. When the naptha is detonated in a spectacular explosion, Steve and Stooge escape to freedom.When Tracy learns of the stunning escape, he immediately fears for Junior’s safety and races to Silver Mountain, Colorado where Junior is living with his father Hank Steele. Hank, Junior and Pat Patton take refuge on an east coast cruise ship while Dick can work to recapture Viller and the Tramp.Back in the city, Tracy and the Chief respond to a jewelry robbery by the mysterious woman named Maxine. Maxine gets the drop on the two and her gang escapes. Maxine turns out to be Maxine Viller, Stooge’s sister and he and Steve show up at her homeseeking refuge. Maxine is unhappy to have wanted criminals in her home, already worried because one of her men was caught by Officer Milligan. The captured man ratted out Maxine’s home and her fence, a man named Gyp Reed. Milligan and Tracy stake out the Viller home and observe Maxine sending her dog Satan out as a courier to the fence. The two follow the dog, subdue Gyp and Satan and wait for Maxine to arrive with the jewelry. Maxine doesn’t show, instead it’s Steve the Tramp with the jewelry and after a brief fight he and Gyp are arrested.Milligan and Tracy return to the Viller household to arrest the remaining criminals and Milligan is tricked by Maxine with a gas filled walnut. Tracy and Milligan are incapacitated and Stooge and Maxine escape. Officer Farney and the Chief arrive just in time to save the gassed detective and Doctor Effting an expert on gas from Mercy Hospital is called to get the two back on their feet.Stooge and Maxine steal a plane for Canada with a goal of escaping by ship to Europe. Meanwhile Hank, Junior and Patton’s ship has hit ground off the coast of Canada and both groups end up in the same harbor in Halifax. Stooge is the first to see them and he lures his foes into a warhouse where he knocks out Pat Patton and reaches for Junior. Even though he’s blind, Hank Steele fights back to protect his son and Stooge shoots Steele in the chest and then runs in panic. He and Maxine board a cruise ship for Europe but Stooge doesn’t think they’ll make it and dives off into the harbor where Patton takes several shots at him. Patton belives he killed the man but Stooge actually escapes.
Having feigned his death, Stooge Viller is hiding out in Halifax, Canada when he is knocked unconscious and shanghaied by the crew of a smuggling ship called “The Bat”, captained by Old Mike. Old Mike takes one look at Stooge and has his men release his old smuggling ally. Stooge asks to join Mike as a partner and though Mike refuses, the two plot together to get their hands on the money Hank Steele’s estate is passing on to Dick and Junior Tracy.Stooge procures a boat of his own and disguises himself as an old bearded sailor, visiting Tess Trueheart and telling her Dick Tracy is badly hurt in the harbor and is asking to see her. Tess goes with Stooge and is held captive aboard Mike’s boat. Dick returns from the funeral for Junior’s dad in Colorado and he and Junior visit Tess, finding out from Mrs. Trueheart that Tess was taken to the harbor and Tracy begins to suspect Stooge may be alive.Posing as a harbor boy, Junior uncovers Stooge’s boat where they easily arrest Stooge. The clever criminal refuses to reveal Tess’s location on Old Mike’s ship but Tess escapes into the water on her own and Tracy and Junior rescue her and then raid Mike’s ship, arresting the old sea dog. In the jail house, Old Mike tells the police he’ll fess up if he can see his ship one more time, but once aboard with a police entourage he triggers a dynamite booby trap, blowing up himself and half the ship. Quick observation by Junior manages to save Dick and Junior from a similar fate.
Two young car thieves see Junior and hire him to be a lookout while they steal a car and he calls them in to the police. Tracy and Patton quickly arrive, arrest one hoodlum and trail the second to his superior, a man named Slicer. Slicer cracks under pressure and spills the details on an old Ice Factory meeting where Tracy arrests a man named Duke and the entire gang.After the raid, the police find a detailed ledger of official people, vehicles and travel patterns used by the gang in their thefts. Tracy suspects a political connection to the ledger and visits Mayor Freddy “Glad Hands” Turner to voice his suspicions. Needing another lead, the Doc Gauger and the department administer a truth serum (Scopolamine) to Slicer but before he can name the boss in charge a gunman breaks in through the window with a pistol, holds up Tracy, Doc and Patton and escapes with Slicer.Slicer and the gunman soon go to work with a protection racket, killing a non-paying grocer named Benny and pineapple bombing another store. When Tracy meets with Chief Brandon, Mayor Turner and State’s Attorney King, an assassin shoots through the window hitting Tracy’s hand. Tracy vows to bring this organization to justice and has Tess and Patton open a Delicatessen in the racketeer’s neighborhood as bait. The plan works perfectly and they arrest “Slip” Buckley and an accomplice. Patton follows a third man named Barney who was acting as lookout to Boss Jim Herrod’s mansion. Herrod was a former politician with many connections in city hall.Barney drives to the pen and Tracy and Patton apprehend him. Patton goes inside the jail dressed as Barney and learns that Big Boy Caprice has been running the criminal empire from the slammer and Boss Herrod is his primary lieutenant. Tracy goes to the Mayor’s office to tell the Mayor, where he encounters and confronts Boss Herrod. Two of Herrod’s bodyguards come in shooting, wounding the Mayor and dragging their boss out of the office. Tracy, Herrod and the bodyguards engage each other in a city hall shootout. Boss Herrod is gunned down and the bodyguards are arrested by Milligan and Chief Brandon.
Big Boy is furious after the arrest of Boss Herrod and while still in jail demands Tracy’s elimination. Dick’s home is firebombed bringing a momentary smile to Big Boy’s face until he learns Tracy arrested his lieutenant “Nose” Riley the next day. A couple of Big Boy’s men, Curley and Bill observe Tess and Junior waiting in a car for Tracy outside the station. Curley takes the two captive and while Bill holds them up out of side Curley dresses as Tess and waits in the car. When Dick arrives Curley draws a gun on him and drives him to a safe house where a cohort named Barney is waiting.Muscle man Bill joins up with an accomplice named Duke and the two drive Tess and Junior to the same hideout. Junior causes trouble in transit and the two throw the kid off a bridge and into a river. At the hideout Tess is tied up with Tracy and Big Boy arrives to gloat having busted out of prison by taking the warden hostage with a gun he had smuggled in. The criminals light the house on fire with Tracy and Tess inside and watch while smoking cigars from a nearby hill.The two lovebirds are saved when Junior (who has survived) runs in to the burning building and unties them. When escaping the flaming structure Junior is badly burned and Tracy carries him outside where Big Boy and his men are waiting. Big Boy lines Tracy and Tess up against the building, preparing to execute them with his tommy gun but Chief Brandon and Pat Patton arrive just in time and Patton shoots Big Boy in the leg. The criminals escape, both sides racing to find a doctor for their wounded. Big Boy pulls over a doctor named Oiler on the road and forces him to fix his leg. Doc Oiler, a specialist in burns is cut loose by Big Boy and soon helps save Junior’s life.
From hiding Big Boy sends “Confidence” Dolan to collect $10,000 in travel money from his lawyer Ben Spaldoni. Spaldoni hands over the cash but then has a thug named Nick steal it from Dolan knowing that Dolan will be on the hook for it. Needing to earn $10,000 fast, Dolan brings a pal named Sandy Maguire into a scheme to steal $20,000 in bond money from Joseph White. Dolan made a deal with Mr. White’s son Jimmy to split the bond money. The two use a kid named Donnie Gimley as the money courier but when he’s hit by the car the bonds are recovered by the police. After a short chase, “Confidence” is arrested and Sandy is shot to death by police.Tracy and Junior return the bonds to Mr. White who is overjoyed and invites the two to stay for dinner. Tracy has detective work to do but Junior does stay and gets on well with Mr. White’s older son Jimmy. Jimmy recognizes Junior’s skills and invites him out one night to meet his friends. They call themselves the 25 club, with the goal of becoming rich by 25. This sounds alright to Junior and joins the club. Junior is sworn to secrecy, but that is standard club operating procedure.The 25 club plans to robe a drug store safe and lure Junior in by telling him it is a Christmas party. Jimmy pretends to lose the keys to the store and Junior crawls in a skylight to open the door from inside. When the gang begins to open the safe Junior realizes he’s been duped but Jimmy tells him it is to late, he’s a criminal now.Jimmy drags Junior along to more crimes including a Cigar Shop robbery and a Grocer store stick-up. He even splits some of holdups evenly with Junior, hoping to keep the kid happy. Junior is not happy though, he’s very upset and comes up with a plot to extricate himself from his predicament.Tracy mean while is working the crime spree and gets a description of Jimmy that he immediately recognizes as Jimmy White. When “Confidence” Dolan admits Jimmy gave him the stolen bonds last month Tracy visits Jimmy’s father at home. Jimmy overhears the conversation but isn’t to worried. He plans to use Junior’s involvement to blackmail Tracy.Back at the hideout, Junior is alone under watch by club member Bud. Junior gets the drop on Bud with a pool cue, knocks him unconscious and then recovers all the money from the safe. He seeks out Pat Patton who returns to the hideout with Junior, sending Bud away on the paddy wagon and dressing up as Bud. When Jimmy and his crew return, Patton gathers evidence that Junior was tricked and held against his will and then makes an arrest. Lawyer Ben Spaldoni refuses to work the case when Jimmy’s father doesn’t pony up defense money and Tracy proclaims Jimmy White will get 20 years in jail.