The former Illinois Senator first mixed with the correspondents at the swanky evening on May 9, 2009.

Martin H. Simon-Pool/Getty Images

Martin H. Simon-Pool/Getty Images

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Mandel Ngan/AFP/Getty Images

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Paul Morigi/WireImage

Mandel Ngan/AFP/Getty Images

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Martin H. Simon-Pool/Getty Images

Paul Morigi/WireImage

Paul Morigi/WireImage

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Paul Morigi/WireImage

Paul Morigi/WireImage

Paul Morigi/WireImage

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Paul Morigi/WireImage

Paul Morigi/WireImage

Jeff Snyder/FilmMagic

Paul Morigi/WireImage

Paul Morigi/WireImage

Paul Morigi/WireImage