THE PUBLIC OFTEN VIEWS THE RELATIONSHIP BETWEEN POLICEMAN AND CRIMINAL AS A SIMPLE ONE IN WHICH THE HONEST, EFFICIENT OFFICER HAS ONLY TO LOCATE AND ARREST THE OFFENDER. HOWEVER, POLICE CONTACTS WITH CRIMINALS OFTEN DO NOT OCCUR IN SUCH A SIMPLE CONTEXT. COMPLEX INTERRELATIONSHIPS BETWEEN CRIMINALS AND THE REMAINDER OF SOCIETY HAVE DEFINED AND INFLUENCE THE BEHAVIOR OF POLICE. MANY CRIMINALS HAVE TIES TO LEGITIMATE SOCIETY THAT PROTECT THEM FROM THE LEGAL IMPLICATIONS OF THEIR ACTIVITIES. TO COPE WITH SUCH LAWBREAKERS, POLICE OFTEN HAVE HAD TO COMPROMISE BETWEEN THE THEORETICAL OBJECTIVES AND THE PRACTICAL REALITIES OF THEIR WORK. A REVIEW OF THE PROLIFERATION OF GAMBLING IN THE UNITED STATES DURING THE SECOND HALF OF THE 19TH CENTURY REVEALS A SHIFT FROM A PROFESSION POPULATED BY TALENTED INDIVIDUALS (PROFESSIONAL GAMBLERS AND 'SPORTING GENTLEMEN') TO AN ACTIVITY RUN ON BUSINESS PRINCIPLES. THIS SHIFT OCCURRED SIMULTANEOUSLY WITH CHANGES IN THE STRUCTURE AND THEORY OF POLICING BETWEEN 1840 AND 1887. DURING THIS PERIOD, GAMBLERS CREATED COMPLEX AND SUBTLE CONNECTIONS AMONG THEMSELVES, THEIR CUSTOMERS, POLITICIANS, AND THE POLICE. THESE CONNECTIONS REDEFINED THE CONTEXT IN WHICH LAW ENFORCEMENT TOOK PLACE. BY CREATING CONDITIONS THAT SEVERELY RESTRICTED THE ABILITY OF THE POLICE TO SUPPRESS THEIR ACTIVITIES, GAMBLERS ASSURED THEIR OWN FORTUNES AND LAID THE FOUNDATIONS FOR MODERN 'ORGANIZED CRIME.' NOTES ARE PROVIDED. (AUTHOR ABSTRACT MODIFIED).