Chapter 3 captures a pivotal period in Brown’s life during the 1840s and 1850s, a time marked by personal challenges and increasing involvement in the abolitionist movement. As Brown grappled with bankruptcy and depression, his ideological convictions deepened, leading him toward a path of direct action against enslavement.

The chapter begins with an anecdote about Brown undergoing a phrenological examination by Orson Fowler, in which the latter accurately identified Brown’s strong self-assuredness, leadership tendencies, and financial imprudence. Later Brown embarked on a wool trading venture that ultimately failed due to market fluctuations and Brown’s stubborn business strategies.

Amid these personal and financial struggles, Brown’s abolitionist spirit was stoked by the political and social turmoil of the time, particularly by the Fugitive Slave Act of 1850 and the Kansas-Nebraska Act of 1854. These acts intensified the national debate over enslavement and propelled Brown toward more radical measures. His meeting with Frederick Douglass in 1847-48 and his plans to establish a guerrilla base in the Allegheny Mountains for the liberation of enslaved people illustrate the evolution of his strategy from peaceful resistance to armed insurrection.

Gerrit Smith, a wealthy abolitionist and Brown’s eventual benefactor, persuaded him to move to North Elba, New York, to help Black pioneers farm.