Ben Spaldoni acted as a criminal lawyer late in 1933 and held a portion of Big Boy’s cash. Big Boy sent “Confidence” Dolan to Spaldoni for $10,000 in travel money. Spaldoni gave Dolan the cash but then enlisted a man named Nick to steal the $10,000 away, knowing that Dolan would be on the line for the money. This theft would lead to Jimmy White and Dolan working to steal $20,000 of bonds from Jimmy’s father and both their arrests.
Spaldoni then was revealed to be the lawyer for Jimmy White’s father, but he refused to help get Jimmy out of jail when his father didn’t pony up the cash for bail. Jean Penfield approached Spaldoni and got his help to bail Jimmy out of jail in exchange for his interview for her book. When Spaldoni and Jimmy discovered her manuscript would land Big Boy and many others in prison, they tried to steal the book and kill Jean. The attempts failed and Jimmy himself was killed.
When a vicious fight between Jean Penfield and Tess Trueheart was reported, Spaldoni saw a revenge opportunity, shot writer Jean Penfield and arranged the scene so that it looked like Tess Trueheart shot the woman in a fit of jealousy. Dick Tracy uncovered the deception and engaged Spaldoni and his gang (Mac, Mike and Representative Milrey) in a shoot-out at an abandoned steel mill. Gang member Mike killed, the other two arrested and Ben himself fatally injurred. On his death bed, Spaldoni confessed to his crimes.