 Wilson has been described as "among a very small collection of truly brilliant digital futurists in the media world," by WBUR general manager Charles Kravetz.Wilson, a graduate of the University of Chicago, began his journalism career in 1980 as a crime reporter for Chicago's City News Bureau.Following a print reporting career at "Newsday" from 1988 to 1995, Wilson transitioned into digital media at Congressional Quarterly, where he served in a variety of roles.