[2] Leary graduated in 1968 from Rice Lake High School, where he played tackle for the 1966 Heart o’ North championship football team [3] and competed in the state wrestling tournament.
[7] His brother, Mike Leary, was the editor of the San Antonio Express-News, and while at the Philadelphia Inquirer, directed and edited a series on school violence that won the 2012 Pulitzer Prize for public service.
[13] He has also researched and helped produce several folk life festivals, museum exhibitions, documentary sound recordings, and films, such as The Art of Ironworking Archived 2013-05-07 at the Wayback Machine.
[9] Leary co-produced Down Home Dairyland with Richard March for Wisconsin Public Radio from 1988 to 1995.
[14] In his book, Polkabilly: How the Goose Island Ramblers Redefined American Folk Music, Leary proposes a redefinition of traditional American folk music and proposes a new genre known as "Polkabilly".