Preventive detention provisions in the US and Canada assume we can identify, in advance, individuals at high risk for sexual recidivism. To test this assumption, 377 adult males with a history of sexual offending were followed for 20 years using Canadian national criminal history records and Internet searches. Using previously collected information, a high risk/high need (HRHN) subgroup was identified based on an unusually high levels of criminogenic needs ( n = 190, average age of 38 years; 83% White, 13% Indigenous, 4% other). A well above average subgroup of 99 individuals was then identified based on high Static-99R (6+) and Static-2002R (7+) scores. In the HRHN group, 40% reoffended sexually. STATIC HRHN norms overestimated sexual recidivism at 5 years (Static-99R, E/O = 1.44; Static-2002R, E/O = 1.72) but were well calibrated for longer follow-up periods (20 years: Static-99R, E/0 = 1.00; Static-2002R, E/O = 1.16). The overall sexual recidivism rate for the well above average subgroup was 52.1% after 20 years, and 74.3% for any violent recidivism. The highest risk individuals (top 1%) had rates in the 60%–70% range. We conclude that some individuals present a high risk for sexual recidivism, and can be identified using currently available methods.