Labelled the "face of the justice system" (Law Commission of Ontario 2011 as cited by the Ministry of the Attorney General of Ontario 2015d), the Provincial Offences Administration of Ontario (POA) - a regulatory system created to decriminalize minor offences - remains an understudied program and field. Addressing this gap, this thesis analyzes the politico-juridical problematizations of cost, volume, and revenue at the center of the POA and the 'modern fine's' (Bottoms 1983) construction. Understanding punishment as both a by-product and shaper of social structures (Garland 1990), it observes the dialectic role of the POA as perpetuating neoliberal structures, consequently reinforcing the Administration's monetization. Located within this regressive economic model, this study also observes the emergence of a new 'debtor prison'. In delineating the outcomes and limitations of decriminalization, this thesis calls for a re-imagining of the POA so that it may achieve the proportionality it purports to pursue.