Robert Weakley spent his formative years in Halifax County, Virginia, before studying surveying in Rowan County, North Carolina. He relocated to the Cumberland settlements in Davidson County and engaged in agricultural pursuits in what later became Tennessee. Weakley held various military positions, including colonel in the militia, and participated in the Revolutionary War. He served in multiple capacities within Tennessee's state government, including the House of Representatives, Senate, and as Speaker of the Senate. Weakley also contributed to the early economic development of Tennessee through land speculation and infrastructure projects, such as the Nashville Bridge Company and the first covered bridge over the Cumberland River.

Robert Weakley's political identity is marked by a blend of economic pragmatism and infrastructural innovation, underscored by a long history of military service. His advocacy for the Nashville Bridge Company reveals a strategic focus on leveraging infrastructure for economic growth, while his role in the construction of the first covered bridge over the Cumberland River highlights an innovative approach to regional development. Weakley's involvement in Indigenous relations, as seen through his appointment as a commissioner to treat with the Chickasaw Indians, adds a layer of complexity to his political persona, suggesting a nuanced stance on Native American affairs.