From 1965 to 1966 he was the assistant director of Northwestern University's summer institute for teachers of disadvantaged youth.
[4] In Rochester, Wilson dealt with the aftermath of the city's first teachers' strike and a major fiscal crisis that forced the closing of 10 schools.
However, Wilson was credited with raising test scores, imposing discipline, and improving the district's image.
[6] During his tenure in Boston, Wilson dealt with the end of W. Arthur Garrity Jr.'s involvement in Boston's school desegregation, budget cuts, a near bus drivers strike, fires that damaged two school buildings, and the AIDS epidemic.
[11] In 1991, the New Jersey Department of Education appointed Wilson to lead the Paterson Public Schools after the district was taken over by the state.
In October 2000, Wilson was charged with DWI after he crashed a school vehicle on Interstate 84 in New Jersey.
[15] In 2002, Wilson was appointed to a five-member board that oversaw the Roosevelt Union Free School District after it was taken over by the state of New York.