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One of the owners of the Puerto Rico Islanders, he was elected president of the club in 2006, and has been the public face of Puerto Rico's first professional soccer franchise and the U.S. territory's only professional team in a national league, since Puerto Rico does not have an MLB or NBA team. Guillemard has made it a point to demonstrate that a Puerto Rican team can excel nationally. In 2010 he became the majority owner after other owners sold their shares of the club to him as a way of meeting the new USSF D2 standards.
A prominent supporter of statehood for Puerto Rico, during the 2008 Puerto Rico June 1 Democratic presidential primaries, he coordinated now President of the United States Barack Obama's campaign which, although unsuccessful locally, was successful nationally. He subsequently served as a member of the 2008 Democratic National Convention Platform Committee and was responsible for drafting the platform plank regarding Puerto Rico.
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