 He engaged as superintendent of the Pierce County, Wisconsin schools until 1881, when he resigned and moved to Minnesota and became State institute conductor of Minnesota and professor in the normal school in Mankato, Minnesota.He was president of the Minnesota Educational Association in 1891.McCleary was elected as a Republican to the 53rd, 54th, 55th, 56th, 57th, 58th, and 59th congresses, holding office from March 4, 1893, to March 3, 1907.