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n 1853 the Grand Trunk Railroad connected Portland to Montreal and to the grain trade of the Canadian interior. Some three decades later, the city's predominantly Irish longshoremen formed a Benevolent Society and, in an ongoing search for job security in this volatile trade they voted, just before World War I, to affiliate with the International Longshoremen’s Association, hoping “to make this port Union all over." Michael Connolly's article explores the decisions and actions that led up to this important event in Maine's labor history. Dr. Connolly is the grandson of a charter member of the Society. He is Associate Professor of History and Director of the Honors at Saint Joseph's College in Standish, Maine. His Ph.D. dissertation, from Boston College (1988), explored the history of the Portland Irish longshoremen, which is also the focus of his most recent publications.