Prior to the Bush administration, Skinner served as the United States Attorney for the Northern District of Illinois under President Gerald R. Ford from 1975 to 1977, succeeding James R. Thompson.

Although offered position to serve as assistant to the chairman of IBM, Thomas Watson Jr., Skinner decided to enter a career in public service.

From 1984 to 1988, while practicing law full-time, he also served as chairman of the regional transportation authority of northeastern Illinois, the nation's second-largest mass-transportation district.

During his tenure, Skinner was credited with numerous successes, including the development of the President's National Transportation Policy and the passage of landmark aviation and surface-transportation legislation.

In addition, Skinner was instrumental in developing President Bush's Intermodal Surface Transportation Efficiency Act, which served as the catalyst for the whole ITS industry.

After Dick Thornburgh resigned as Attorney General in 1991 to run for the U.S. Senate seat left vacant by the death of John Heinz, Skinner was offered the position.

Skinner served in the position from December 1991 until August 1992, when he was asked to work on the campaign full-time at the Republican National Committee and was replaced as chief of staff by then-Secretary of State James Baker.

Upon leaving the White House, Skinner returned to Chicago and became president of Commonwealth Edison and its holding company Unicom Corporation (now Exelon) from 1993 to 1998.

In 2015, Skinner was appointed chairman of the Takata Corporation independent quality assurance panel to conduct an internal investigation of the company's airbag manufacturing process.

Mayor Lori Lightfoot appointed Skinner to lead the task force to assist the City in its efforts to recover from the economic consequences of COVID-19.

His eldest son, Thomas Vernon Skinner, is the former head of the U.S. Environmental Protection Agency's national compliance program, director of the EPA's region 5, and current general counsel of Louisiana State University.

Another son, Steven Knox Skinner, is the CEO of KemperSports, a privately owned company that manages over 100 golf courses across the country.