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After a fine junior career as a goal scorer with the OHL’s North Bay Centennials, McLlwain joined the Pittsburgh Penguins in 1987-88 and played in Pennsylvania for two seasons. But a summertime trade made McLlwain a Winnipeg Jet in 1989. As a Jet, he enjoyed the finest offensive season of his career, scoring 25 goals and 26 assists in 1989-90.In 1991-92, McLlwain has the distinction of playing for four different NHL teams in a single season. He started as a Jet playing three games, was traded to Buffalo where he skated in five games, was traded to the Islanders, playing 54 games on Long Island, then joined the Toronto Maple Leafs for the final eleven games of their season. McLlwain played 1992-93 with Toronto but with Ottawa entering the league, he was picked up in the Waiver Draft. The dust never really got to settle on Dave’s suitcase, as during the 1995-96 season, he was dealt to Pittsburgh. The next season, he signed with the New York Islanders as a free agent where he ended his NHL career.