His legal career is highlighted by his service as Co-counsel on the case Intertanko v. Locke, winning a unanimous decision before the United States Supreme Court[2] Connaughton was elected Chairman of the Prince William Board of County Supervisors in November 1999, defeating the incumbent, Democrat Kathleen K. Seefeldt.

He also successfully campaigned to bring AOL, General Dynamics, Comcast, Eli Lilly and other major employers to Prince William.

[4] During his tenure Connaughton was consistently cited as one of the best Federal transportation policy leaders by Members of Congress, industry and the media.

After taking office, he initiated multiple audits of the Virginia Department of Transportation which identified more than $1.4B of misallocated funds that were then deployed to advance stalled projects.

Connaughton led efforts to grow private investment in the Commonwealth's aging infrastructure system by establishing a new P3 Office, streamlining the Public-Private Transportation Act process and recognizing innovative financing opportunities.

Under his leadership, a state investment of less than $600 million has been leveraged into over $3 billion worth of infrastructure, ranking Virginia #2 worldwide for P3 deals.

He has overseen the creation of the Virginia Transportation Infrastructure Bank, providing a resource that public-and private-sector entities can use to finance projects and accelerate construction.

Most critically, Connaughton is credited with enabling passage of Virginia's Road to the Future, the first comprehensive transportation funding bill approved in the Commonwealth in 27 years.