After working for Washington, DC's Gibson, Dunn & Crutcher, a firm of over one thousand lawyers worldwide (roughly equal to 25% of the entire Vermont bar), Tom settled in Vermont.  He had a distinguished academic career (cum laude both at the University of Virginia and at the University of Michigan Law School), and he clerked for the New Jersey Supreme Court.

Tom's wife, Carolyn, was a prosecutor with the Chittenden County State's Attorney's office.  They have a son named Nolan and a daughter Calista.  Tom was a founding member and first president of Preservation Burlington, dedicated to fostering appreciation for Burlington's architectural heritage.  He also knows more about baseball history than anyone this side of Cooperstown.  He has edited three books on baseball, Green Mountain Boys of Summer (winner of The Sporting News/SABR Baseball Research Award), Walter Johnson: Baseball's Big Train, (winner of the CASEY Award as best baseball book of the year) and Deadball Stars of the National League.