The man known as "Confidence" Dolan was a subordinate of Big Boy. He had short dark hair that he wore parted in the center and a wide mouth. Dolan often wore a wide-brimmed hat.
Betrayed by Spaldoni[]
After Big Boy escaped from prison and went into hiding, he sent Dolan (whom he trusted) to collect $10,000 in cash from his attorney Spaldoni. Big Boy planned to use the money to flee the country.
Unbeknownst to Big Boy and Dolan, Spaldoni was not trustworthy. After giving the money to Dolan, Spaldoni arranged for some confederates to assault Dolan and steal the money, which they would then split with Spaldoni. Dolan knew that Big Boy would blame him for losing the money and attempted to replace it.
The Stolen Bonds[]
Dolan contacted his friend Sandy Maguire and arranged to transport some bonds that had been stolen from Joseph White. The plan involved using a young boy as a decoy. The scheme went awry and the boy was hit by a truck while crossing the street. This attracted the attention of Dick Tracy.
The boy was placed in the same hospital room where Junior was recovering from an injury. Dolan sent Maguire to kidnap the boy before he could make a statement to police, but Maguire abducted Junior by mistake. Junior was able to get Maguire's pistol and attempted to take Dolan and Maguire to the police. They were intercepted by two of Maguire's friends and Junior became a captive once again. Dolan tortured Junior by pressing his body into a wall with a heavy desk.
Dolan and Maguire then sealed Junior inside an empty water heater in the basement of Dolan's home. Junior was able to free himself, and Dick Tracy arrived just as Dolan and Maguire were preparing to leave. After a series of reverses, more police arrived and Maguire was shot to death as he was planning to kill Tracy. Dolan was also injured and he was taken into custody. He was then identified by the injured boy.
In exchange for identifying Joseph White's son Jimmy White as the man who supplied the stolen bonds to him, Dolan was allowed to serve his prison sentence out-of-state, where he would presumably be safer from reprisal by Big Boy.