This Article seeks to examine judicial opposition to New York’s 2020 criminal justice reforms in the context of existing scholarship on judicial organizational culture to understand why judicial obstruction occurs and how it can be addressed. New York’s 2020 criminal legal reforms sought to reduce pretrial detention and to provide greater access to discovery for the defense by curtailing judicial discretion to set bail and judicial power to excuse prosecutorial discovery delays. But judges opposed the law both surreptitiously and openly through defiant opinions, administrative adjustments, and routine court actions that undercut the reforms’ intended effects. Scholars such as Malcolm Feeley, Brian Ostrom, and Roger Hanson have written about how the informal organizational culture of a court system can be an impediment to reforms. Their analysis applies to New York’s 2020 reforms and provides insight into why this specific resistance occurred and how it can be addressed. The judiciary was included in planning and discussing the 2020 reforms and the reforms sought to remove judicial discretion in the matters of bail and discovery. Yet when it came time to implement the change, judges used other powers to avoid releasing individuals and to avoid sanctioning prosecutors. This is at least partially due to New York’s judicial appointment scheme which makes the judiciary sensitive to structural narratives concerning public safety and court leniency. Although these reforms were democratic and popular, judges were not sufficiently incentivized to properly implement the changes. If reforms are to succeed, the popular and political will to pass the reforms must extend beyond the passage of the law and must also create mechanisms to scrutinize, guide, and support the judiciary’s implementation of the law.