The chapter explores how the shift from retributive to preventive justice affected the constitutional balance between judicial and administrative sentencing powers. After analysing the Spanish law framed by De Asúa on the dangerousness without crime, it compares the European solution of the measures of security with the US indeterminate sentence system, stressing the European attitude in favour of judicial sentencing jurisdiction. It examines the growth of penal administrative powers in the United States, focusing on the shift from legal rules to legal standards in sentencing discussed by Roscoe Pound, Felix Frankfurter, and Sheldon Glueck, and then describes the hybrid system of penal/administrative security measures provided for by the 1930 Italian Fascist Code. The chapter finally investigates the different positions on the powers of the judge in the sentencing phase debated at the Berlin Congress in 1930 and the ambiguities of the dual-track system.