Research Summary We examined race‐group differences in the effects of how felony defendants are treated at earlier decision points in case processing on case outcomes. Multilevel analyses of 3,459 defendants nested within 123 prosecutors and 34 judges in a large, northern U.S. jurisdiction revealed significant main and interaction effects of a defendant's race on bond amounts, pretrial detention, and nonsuspended prison sentences, but no significant effects on charge reductions and prison sentence length. Evidence of greater “cumulative disadvantages” for Black defendants in general and young Black men in particular was revealed by significant indirect race effects on the odds of pretrial detention via type of attorney, prior imprisonment, and bond amounts, as well as by indirect race effects on prison sentences via pretrial detention and prior imprisonment. Policy Implications The consideration of cumulative disadvantage is important for a more complete understanding of the overincarceration of Blacks in the United States. Toward the end of reducing racial disparities in the distribution of prison sentences, courts might (a) reduce reliance on money bail, (b) consider bail amounts for indigent defendants more carefully, and (c) increase the structure of pretrial decision making to reduce the stronger effects of imprisonment history and type of attorney on the odds of pretrial detention for Black suspects.