Since the start of the war on drugs, studies have found racial and ethnic disparities in sentencing outcomes among defendants convicted of drug offenses; however, several gaps in the drug literature remain regarding disparity-producing mechanisms, the role of drug offense characteristics, disparities in understudied groups, and possible solutions to unwarranted disparities in drug case outcomes. Using felony case-level data from the state of Florida (n = 3,058 felony drug cases), this dissertation examines three interrelated studies. Study 1 examines bail and pretrial detention practices as disparity-producing mechanisms in drug offense cases. The results of Study 1 suggest that significant variations in bail schedules in Florida’s 20 judicial circuits result in jurisdictional variation in the likelihood of pretrial detention, which subsequently, results in jurisdictional variation in pretrial and sentencing outcomes among drug offenders, given the direct effect of pretrial detention on case outcomes. Study 2 examines racial, ethnic, and immigration status disparities in pretrial and sentencing outcomes across various types of drug offenses and drug substances. The results of Study 2 suggest the presence of racial and ethnic disparities in drug case outcomes in Florida’s circuit courts, as well as the moderating role of drug offense characteristics on the effects of race and ethnicity on pretrial and sentencing outcomes. Study 3 examines whether progressive chief prosecutors, who campaign on a platform to reduce and, in some cases, refuse to prosecute low-level drug offenses, handle drug offenses differently than traditional prosecutors. The results of Study 3 indicate support that progressive chief prosecutors in Florida reduce mass incarceration and unwarranted racial and ethnic disparities in case processing and sentencing outcomes in drug offenses; however, there is still room for improvement in the progressive prosecution movement in Florida. The results of each study have direct implications for theory and policies aimed at creating a more effective and fair criminal justice system.