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With more than 30 years in the newspaper industry, Woolsey joined Southern Newspapers in 2014 after working 20 years with Paxton Media Group serving as publisher and eventually group publisher. Besides serving in smaller communities, Woolsey's experiences also include managing properties in metro markets, including St. Louis, Pittsburgh, Chicago, and Atlanta. Woolsey is also a longtime Rotarian, board member for America’s Newspapers, Texas Press Association as well as local organizations including the Boys & Girls Club, and The Salvation Army. Woolsey is a native of Kansas City, Missouri, and is married to his college sweetheart, Maryrine Woolsey. They have two adult children. In his spare time, he likes to read, write, travel, surf, and plink on a piano.