A list of crime bosses, gang leaders and other high level criminals Tracy has faced off against over the years.
| Name | Active Years | Brief Bio | Last Status |
|---|---|---|---|
| Big Boy | 1931, 1932, 1933, 1934, 1978 | Big Boy was a kingpin of crime in Dick Tracy's town and responsible for making Tracy a cop. | Dead |
| Dan Mucelli | 1932 | Dan ran a dope ring and shot Dick Tracy to evade capture. Dan was eventually apprehended. | Jailed |
| Larceny Lu | 1932, 1934 | Larceny Lu and her gang ran a stolen auto parts ring which was uncovered by Junior. Lu would again see action with Steve the Tramp and Doc Hump before her second arrest. | Jailed |
| Boss Herrod | 1933 | Herrod was a retired politician who ran rackets in the city for Big Boy and instigated a gunfight at City Hall. | Dead |
| Cut Famon | 1935 | Ran a protection racket in the city. | Dead |
| Bookie Joe | 1935 | Bookie ran a gambling syndicate in the city. | Dead |
| Lips Manlis | 1936 | Former gang boss who redeemed himself and worked with Tracy under the name Bob Honor. | Free |
| Danny Supeena | 1937 | Gang leader who dabbled with insurance scams. | |
| Mayor Chiang | 1938 | Mayor of Chinatown and Boss of a slave cartel. | Dead |
| Junky Doolb | 1940 | Gang leader and murderer arrested and then killed while escaping jail with an empty gun. | Dead |
| Jerome Trohs | 1940 | Short lawyer who took control of Junk Doolb's gang with his girlfriend Mamma. | Dead |
| Czar Rennis | 1941 | Crime boss in the gambling racket, Czar was killed by his own henchman. | Dead |
| Littleface Finney | 1941 | Violent gang leader who led a stolen gem racket before things went sour with Dick Tracy. | Free |
| Jacques | 1942 | Blackmailer and con-man, former owner of the Bird Club. | Dead |
| B-B Eyes | 1942, 2011, 2012, 2013 | Bootlegger, kidnapper with a grudge towards Dick Tracy. | Free |
| 88 Keyes | 1943 | Piano player and secret head of gang specializing in murder. | Dead |
| Measles Enog | 1945, 1981, 2012 | Organized a dope dealing operation into a local prison using his mother on the inside. | Dead |
| Shoulders | 1946, 1948 | Tough man who provided protection to street criminals and would later take up robbery and murder. | Dead |
| Coffyhead | 1947 | Coffyhead attempted to end Junior's Crimestopping Club but ended himself instead. | Dead |
| Mrs. Volts | 1948 | Electrical supply thief and racketeer. | Dead |
| Big Frost | 1948, 2011 | Racketeer responsible for the murder of the scientist Brilliant. | Dead |
| P.S. Tone | 1949 | Pear-shaped swindler and jewelry thief who would go straight after his arrest. | Free |
| The King | 1951 | Head of a large criminal syndicate, "The King" was Big Boy's successor. | Dead |
| George Alpha | 1952 | Known as Mr. Crime, Alpha was the head of a large criminal organization. | Dead |
| Odds Zonn | 1953 | Criminal who tried to take over Mr. Crime's empire after George Alpha died. | Dead |
| Open-Mind Monty | 1954 | Ran a jewelry ring and teamed up with Dewdrop Hepbeat to kill Dick Tracy. | Jailed |
| Rughead | 1954 | Headed a stolen fur racket and tried to have Dick Tracy killed once uncovered. | Dead |
| Charley Hardley | 1959 | Wheelchair bound head of a slot machine syndicate. | Dead |
| Willie the Fifth | 1959, 2011 | Head of a city crime syndicate who wanted Lizz Worthington dead. | Dead |
| Ace of Spades | 1962 | Leader of the 52 Gang | Jailed |
| Piggy Butcher | 1967 | A vile pig headed mob boss who ran afoul of the Chin Chillars. | Dead |
| Mr. Intro | 1968 | Underworld boss who worked with Purdy Fallar to steal Moon gold. | Dead |
| The Brain | 1974 | Brain obsessed mob boss looking to recovered $2 million in stolen money. | Dead |
| Flipside | 1987 | A music producer and organized crime boss. | Dead |
| Pinhead | 2002 | Bank robber and leader of a gang of "Heads". | Jailed |
| Red Hawk | 2002, 2003 | Triggerman and leader of the Bird gang. | Dead |
| The Chameleon | 2003 | Led a gang of bank robbers that have hit 16 cities in the U.S. | Jailed |
| Mousse | 2004 | Mob boss with a sweet tooth responsible for a massive police bribery operation. | Dead |
| Fiendish Fred | 2004 | Mastermind and leader of the All Purpose Gang. | Hospitalized |
| Royal Flush | 2007 | Led a team of card themed criminals. | Jailed |
| Baskerville | 2008 | A criminal who organized bank robberies. | Dead |
| Big Ace | 2009 | Criminal mind behind a series of high value casino robberies. | Jailed |
| Panda | 2011, 2012 | A lieutenant for Mr. Crime, Panda basically ran things after his release from prison. | Dead |
| Davey Mylar (Mr. Crime) | 2011, 2012 | A computer nerd who became the new Mr. Crime. | Dead |
| Venus | 2013, 2014 | Leader of the Black Hearts, a major criminal group in the city. | Free |