Robert Tripp Ross began his career in various sectors, including real estate, advertising, and auto sales. He later transitioned to the pharmaceutical industry, managing a pharmacy in New York City. By the mid-1940s, he held a significant corporate role in the drug industry. Ross entered politics, winning a congressional seat in 1946, though he faced electoral defeats in subsequent years. He also held leadership positions in sales and marketing for a sports-related company and served as Queens County District Attorney. After his political career, Ross continued to work in business, holding a vice presidency at a merchandising company and a governmental advisory role in Queens.

Robert Tripp Ross's political career reveals a strategic blend of regional economic advocacy and pragmatic opportunism, as seen in his unexpected alliances on environmental regulations. His diverse professional background, from real estate to pharmaceuticals, suggests an ideologically flexible approach, adept at navigating complex policy landscapes. Ross's shifts between public office and private sector roles hint at a calculated balancing of public service and private interests, raising questions about the motivations behind his policy decisions.