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Across the country, police officers consistently have the ability to exercise more discretion than just about any other criminal justice actor and this discretion—to issue stops, citations, arrests, and warrants—plays a significant role in determining the size of our nation’s criminal justice population, especially our jail populations. This is an especially important conversation now (especially at the local and state level), as the decreasing national arrest rates of the past several years—which drove down correctional populations— are contrasted against recent trends in policing rhetoric, which have historically contributed to the sharp growth of our nation’s criminal justice system over the past few decades. Our ability to shrink the national correctional population hinges upon further and sustained reductions of punitive police enforcement. This paper will propel a conversation about law enforcement and local jail population growth, using existing research and data at both the national and local levels to answer questions about the changing relationship between law enforcement and jails and opportunities for change.