[1] McElroy began a career as an educator teaching social studies and English at Lockwood Junior High School in Warwick, Rhode Island after graduation.
McElroy stayed personally involved in the life of the union by handling negotiations and arbitrations for many of RIFT's education locals.
[1] In November 1991, the AFT's long-time secretary-treasurer, Robert G. Porter, died after heart surgery and in 1992, McElroy was elected as his replacement.
[3] McElroy announced on February 12, 2008, that he would retire at the AFT's regularly schedule biennial convention in Chicago, Illinois, in July 2008.
[3] He was succeeded by New York City United Federation of Teachers President Randi Weingarten on July 14, 2008.
[2] He served on the boards of the Amalgamated Bank of Chicago, Working America (an affiliate of the AFL-CIO) and the National Labor College (formerly the George Meany Center for Labor Studies), the National Endowment for Democracy, and Education International headquartered in Brussels.
[1][2] McElroy served as a member of the Debt Reduction Task Force at the Bipartisan Policy Center.