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In 1988, three years into his law career, Mike Pence (R) turned his focus on ousting Democratic Rep. Philip Sharp (Ind.). Pence relied heavily on negative campaigning, including attacks on Sharp for his reliance on political action committee contributions. The 29-year-old Pence even earned a Blue Room photo opportunity with then-President Ronald Reagan — “I felt like I was talking to Mt. Rushmore,” Pence would later say — that August. And yet, Pence fell to Sharp, who defeated the Republican again two years later. He finally won a seat in the House on his third try, in November 2000.