She graduated from the University of Illinois, Phi Beta Kappa with a B.A. in political science and was a Chancellor's Scholar.[4] In 2007, she received her J.D. from Harvard Law School, where she won best brief in the Harvard Ames Moot Court semi-final and final rounds of competition.[5][6] She has worked in Chicago, Illinois, as an associate attorney at Sidley Austin LLP and at Burke, Warren, MacKay & Serritella.[5] She later was a commercial litigation attorney for Meyer Capel law firm in Champaign, Illinois.[7][8] In 2022, she was appointed by the Illinois Supreme Court as executive director of the Commission on Professionalism.[8]
She became Miss America 2003 on September 21, 2002 (as Miss Illinois 2002). Her official platform was "Preventing Youth Violence and Bullying: Protect Yourself, Respect Yourself." Her platform choice grew out of personal experience; she recounted having been the subject of racial and sexual harassment[9] while growing up. In a May 2, 2003, speech, Harold said when she turned to teachers and school administrators, her concerns were dismissed.[10] As part of her platform, she became a national spokesperson for Fight Crime: Invest in Kids, a national advocacy group.[11]
In the first week of her reign, she also adopted a secondary platform for sexual abstinence.[9]The Washington Times suggested that pageant officials demonstrated a liberal bias when they allowed Miss America 1998Kate Shindle, whose platform was HIV prevention, to advocate condom distribution and needle exchange during her time as Miss America.[9] On October 8, 2002, Harold gave a speech at the National Press Club in Washington during which she stated that she would talk about sexual abstinence and that she "will not be bullied" into dropping the topic from her platform.[12] Thirty-eight members of Congress sent her a letter of support, encouraging her to press on with her "healthy message of abstinence until marriage."[13] During her time as Miss America, Harold interacted with legislators and testified before Congress on bullying and abstinence, which provided her with additional motivation to pursue a political career.[14]
In May 2012, Harold was one of four finalists for the Republican nomination for Congress in Illinois's 13th district, a nomination selected by the Republican chairmen of the 14 counties covered by the 13th Congressional District, instead of a primary election.[18] The Republican chairmen selected Rodney L. Davis, over Harold, and Davis was subsequently elected to Congress, in an expensive race.[7][19]
On June 4, 2013, Harold announced she would run against Rep. Rodney L. Davis, R-Ill. in the 2014 Republican primary for Illinois's 13th congressional district.[20][21] Davis, Harold's opponent in the primary, was among the top targets for Democrats in 2014.[22] On March 18, 2014, Harold lost the Republican primary to Davis 54%–41%.[23][24]
On August 15, 2017, Harold announced that she would seek the Republican nomination to be Illinois attorney general.[25] On March 20, 2018, she won the Republican nomination for attorney general garnering 59% of the vote in a two-way contest against Gary Grasso, a former mayor of Burr Ridge, IL, now a member of the DuPage County Board and a litigation attorney.[26] She lost the general election to Democrat Kwame Raoul garnering 43% of the vote to his 55%.
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