Tucker Isaacs, son of German Jewish merchant David Isaacs and Nancy West, a free woman of color, was remembered by one Charlottesville resident as "a good citizen and much respected." He played a central role in the development of the town’s main street, constructing brick buildings on land he owned.
Isaacs and his wife, Ann-Elizabeth Fossett, moved with her parents to Ohio in 1838, returning after several years to Charlottesville, where relatives remained in slavery. In 1850 Tucker Isaacs was arrested for forging free papers for his enslaved brother-in-law, Peter Fossett. After the charges were dropped, Isaacs and his family sold their property, returned to Ohio, and bought a 158-acre farm in Ross County, still remembered as a station on the Underground Railroad. Isaacs once tested a civil rights law in a hostile Ohio community. His grandson William Monroe Trotter wrote of his “brave devotion to liberty and equality.”