Leland also served as the finance chair and senior advisor to the successful 2006 gubernatorial campaign of Ted Strickland, for which he helped raise a record $17 million.

In 1973, at age 20, Leland ran unsuccessfully for election to the Columbus, Ohio Board of Education, coming in fourth in a field of nine candidates (including three incumbents) for three open seats.

[5] In 2002, Leland became national director of Project Vote a group which registered 2.7 million low-income and minority citizens as voters between 1982 and 2002.

[3] After Leland's terms at both the ODP and DNC concluded in 2002, he launched a bid for Democratic National Committee Chair in 2005, with the position going to former Vermont governor and presidential candidate Howard Dean instead.

He was re-elected in 2020 without opposition Until 1996, Leland was counsel to the Columbus law firm of Schwartz, Kelm, Warren and Rubenstein.

An avid baseball fan, Leland served on the board of directors of the Columbus Clippers, the Cleveland Guardians’ AAA franchise, from 2005 to 2023.

During his tenure the Clippers won two National Championships and constructed a state-of-the-art, baseball complex named Huntington Park.