Gregory won a special election to the State Senate in December 2012 to succeed long-time Republican incumbent David L. Williams, who stepped down after twenty-five years in office to become a judge of the 40th Circuit Court. She polled some 80 percent of the vote to defeat Bill Conn, a teacher from Williamsburg, Kentucky, who describes himself as a Conservative Democrat. Among those campaigning for Gregory were U.S. Senator Mitch McConnell, U.S. Representatives Hal Rogers and Brett Guthrie, and Robert Stivers of Manchester, the successor to David Williams as president of the state Senate. The preceding month, on November 6, 2012, Gregory had won a second two-year term in the Kentucky House of Representatives from Wayne, McCreary, and a portion of Pulaski counties. In the changed districting plan, Gregory's district acquired Taylor County. Taylor County had previously been represented by Republican Jimmy Higdon, a Taylor County native and long-term resident of Lebanon in Marion County. Gregory's new counties were part of the Lake Cumberland Area Development District. Green River Lake is located in Taylor County near Campbellsville. The revised districts were required when the Kentucky Supreme Court struck down the 2012 districting on the grounds that it did not comply with the federal "one man, one vote" concept. Democratic GovernorSteve Beshear then called a special session of the legislature to redraw the district boundaries; the state population in 2010 increased from 4 million to 4.3 million. The approved changes took effect immediately on August 23, 2013. Gregory was the chairman of the Senate Government Contract Review Committee, vice-chairman of the Agriculture Committee, and a member of two other committees: Appropriations & Revenue and Judiciary. Gregory served in the House from January 2011 to December 2012. Oddly, she was both preceded and succeeded in that position by fellow Republican Ken Upchurch of Monticello, who had been initially elected in 1998 and stepped down in 2010 to run for county judge, only to return two years later.
2014 election
Gregory lost the Republican primary to George Maxwell Wise, who teaches political science and international studies at Campbellsville University in his native Campbellsville in Taylor County. He is the son of George Wise and Donna Wise, former women's basketball coach at Campbellsville University. In his campaign, Wise promised not seek higher office in the near future, referring to Gregory's sudden successful run for the State Senate after having served in the State House for only two years. Wise said that he has few policy differences with Gregory. Wise remained neutral in the U.S. Senate primary between incumbent Mitch McConnell, whom Gregory endorsed, and the unsuccessful Tea Party challenger, Matt Bevin. The Gregory-Wise primary was expected to highlight regional geographic differences within the district, rather than political thinking. Wise describes himself as "not a cookie-cutter politician" but one who brings "a unique opportunity for the citizens of the 16th district to have a voice in Frankfort that will help change the status quo." In the primary, Wise defeated Gregory, 54 to 46 percent.
