We are living in a moment where open and principled resistance to law and legal order are a part of our daily lives. Whether in support of Black Lives Matter or in opposition to mask mandates, people are in the streets resisting. Over the last decade, the perception of the fixity of our legal order has eroded and so, too, has the stability of our consensus that legality and morality are aligned. In this moment, the visibility and viability of resistance to law and civil government through social movements have surged. With the increasing salience of civil resistance resurfaces an old question: can (and should) judges seek to stand in solidarity with movements engaging in civil resistance? The classic answers to this question take two forms. Judges should either enforce the law and punish the civil resister, or, if they cannot do so in good conscience, they should resign. These answers position the judge outside of and aloof from the political and social struggles that the resisters represent. It follows from this aloof position that judges cannot be in solidarity with civil resistance aimed at legal change in their official capacity. This Article questions the stability of the mainstream conclusion. By focusing my attention on judicial responses to civil resistance against the Fugitive Slave Law of 1850, I return to one of the most influential sources of our collective sense of judicial capacity for political resistance. Through my own original archival research, I revisit Robert Cover’s conclusions about judicial timidity in Justice Accused. Against extensive evidence confirming Cover’s bleak view, I expose and examine one judge’s contrary argument. That judge, Ebenezer Rockwood Hoar, was a neighbor and friend of Henry David Thoreau, and he wrote in conversation with, not against, the strident views of the famous advocate of civil disobedience. Hoar proposed that a judge in sympathy with civil resistance should enforce the law in order to effectuate the power of the resistance. He argued that making Thoreau’s theory of change work required sympathetic judges to enforce the law to expose its injustice. From this colloquy between judge and activist, I draw the beginnings of a counternarrative of how judges may strive towards (if not achieve) solidarity with resistance movements. Judges, like any other institutional actor, have the capacity and perhaps the obligation to be strategic about how they act within and against the social movements that find their ways into their courtrooms.