In 2002, Massachusetts State Treasurer Shannon O’Brien decided to throw her hat in the ring in the race for governor. Her opponent would be one Willard “Mitt” Romney, known for his failed senate run in 1994 and as president of the 2002 Winter Olympics. She went after him, after Barack Obama would do in 2012, over his time at Bain Capital. Mitt went after Shannon over her husband’s ties to Enron. Sparks flew, and O’Brien became the only person ever to go down to Mitt Romney at the polls.

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