The parallels Gates draws between the United States’ past and present are among the most compelling aspects of Stony the Road. Gates contextualizes Obama’s presidency by presenting it against the backdrop of the Reconstruction and post-Reconstruction periods. He compares Obama’s 2008 election to three important events in Black history, namely, the Emancipation Proclamation (1863), the legal abolishment of enslavement with the 13th Amendment (1865), and the Reconstruction Acts (1867-68). Just like Reconstruction, however, the election of the first Black president sparked a backlash that resulted in a rise in white supremacy and a reduction of Black people’s rights. The post-Reconstruction era curtailed Black voting rights and eroded Black people’s gains. Similarly, President Trump attacked his predecessor’s foreign and domestic policy achievements by pulling out of the Iran Nuclear Deal and seeking to overturn the Affordable Care Act (ACA), Obama’s signature healthcare initiative, and the Deferred Action for Childhood Arrivals (DACA), part of the Obama administration’s immigration reform.

The ratification of the 13th Amendment in 1865 brought a legal end to enslavement and involuntary servitude, but de facto enslavement continued with the implementation of post-Reconstruction policies, notably, sharecropping and convict leasing. Sharecropping indebted free Black people to white landowners, keeping them poor while enriching their landlords.