Crash-prone drivers should be effectively targeted for various safety education and regulation programs because their over-involvement in crashes presents a big adverse effect on highway safety. By analyzing seven years of crash data from Louisiana, this paper investigates crash-prone drivers’ characteristics and estimates their risk to have crashes in the seventh year based on these drivers’ crash history of the past six years. The analysis results show that quite a few drivers repeatedly had crashes; seven drivers had 13 crashes in seven years; and the maximum number of crashes occurring in a single year to a single driver is eight. The probability of having crash(es) in any given year is closely related to a driver’s crash history: less than 4% for drivers with no crash in the previous six years; and slightly higher than 30% for drivers with nine or more crashes in the previous six years. Based on the results, several suggestions are made on how to improve roadway safety through reducing crashes committed by drivers with much higher crash risk as identified by the analysis.