As legislatures proliferate novel “enhancements” to criminal sentencing, such as “three‐strikes” and related provisions, and as criminologists debate their effects, the role of existing enhancements, such as habitual offender statutes, has received little empirical attention. This article explores the effect of race in the decision to prosecute and sentence eligible defendants as “habitual” offenders. During FY 1992–93, 9,690 males admitted to prison in Florida were statutorily eligible (two prior felony convictions or one prior violent felony conviction) for sentencing as “habitual” offenders. Approximately 20% received that disposition. They will serve at least 75% of their enhanced sentence as compared with the state average of about 40%. Logistic regression, controlling for prior record, crime seriousness, and other relevant factors, shows a significant and substantial race effect. The disadvantage of black defendants is particularly strong for drug offenses and for property crimes that have relatively high victimization rates for whites (larceny, burglary). Race is less consequential for violent and weapons‐related crimes. Race effects are more often significant in sentencing contexts that are low in terms of percent black, racial income inequality, drug arrest rates, and violent crime rates. The relevance of these findings for a “racial threat” interpretation of sentencing outcomes is discussed.