While living on the farm, the senior Hawkins ran a store and worked picking oranges, while Josephine cleaned and ironed clothing.

The Hawkins were part of a 1917 community effort to raise $300 to build a school for African-American children with support from the Rosenwald Fund.

The Okahumpka Rosenwald School was located a few yards from the Hawkins' home, allowing them to receive an elementary education.

[2] Hawkins' maternal grandfather was Alfred Brown Osgood, a prominent African Methodist Episcopal Church minister and American legislator.

[1] Growing up in rural Florida during the era of Jim Crow laws, Hawkins witnessed many instances of racial violence.

Early in his life, he witnessed several African American men being sentenced to prison for five to six months over a game of ten-cent dice.

[1] As a teenager, Hawkins would return to court on his own to watch trials where African-American people did not have fair or reliable representation.

[1] In 1930, Virgil began attending Lincoln University (Pennsylvania) to earn his bachelor's degree, but was unable to finish due to financial constraint.

Following in his wife's footsteps, Hawkins began teaching at Edgewood, a segregated elementary school in Groveland, Florida.

Finding the segregated school system to be fraught with inequalities in wages, facilities, and supplies, Hawkins again found himself thinking of how he could stand up against the everyday injustices faced by African Americans and returning to his childhood dream of becoming a lawyer.

[9] Finally, "[w]orn and weary from the struggles of the last half of his life, and still unable to retain counsel, Hawkins put down his sword, and attempted to leave the battlefield".