Early career In 1972, at the age of 19, Gray became the second youngest person ever elected as a delegate to the
Democratic National Convention, which was held in Miami. Gray's first run for office was a bid for Lexington Mayor in 2002. He lost the primary and endorsed
Teresa Isaac, who was elected.
Vice Mayor of Lexington In 2006, Gray ran for one of three Council-at-Large seats in the Lexington-Fayette Urban County Council and was elected. As the largest vote-getter among the council-at-large candidates, Gray became vice mayor and served from 2007 to 2010. During his term as vice mayor, Gray expressed opposition to proposals for CentrePoint, a planned hotel, residential and retail complex that was to be built downtown at an estimated cost of $250 million. During the campaign, Gray developed the "Fresh Start Plan," containing a pledge to run the government like a good business, with increased transparency and efficiency and with reduced spending and debt. In November 2010, Gray defeated Newberry 53% to 46% and became one of the nation's few openly gay mayors, and the first openly gay mayor in the city's history. Before his inauguration, Gray had the entire Mayor's Office moved from the 12th floor of Lexington's Urban Government Center to a first-floor ballroom, creating an open office atmosphere that was inspired by his own office at Gray. To learn more about the operations of modern, large city government, the newly elected mayor paid a visit to New York City Mayor Michael Bloomberg. Gray has publicly stated that his administration would focus on three areas: creating jobs, making government more efficient, and building Lexington into a great American city. Gray was re-elected mayor by a wide margin
in 2014.
Built environment projects A staunch proponent of historic preservation and
adaptive reuse, Gray has championed multiple projects that repurposed historic properties and remade public spaces with a greater emphasis on design. Examples from his terms in city government include the
Historic Fayette County Courthouse,
21c Museum Hotel, Lexington's Distillery District, Town Branch Commons (a 22-mile walking and bicycle trail) Town Branch Park, and renovations to
Rupp Arena and the Lexington Convention Center. In 2023, the
University of Kentucky College of Design opened the Gray Design Building, a new collaborative learning space located in a former tobacco warehouse. Gray, Inc. donated $5.2 million to the college to support the project.
U.S. Senate campaign On January 26, 2016, Gray announced that he was running for the
United States Senate in 2016 for the seat then and currently held by U.S. Senator and former presidential candidate
Rand Paul. The senate race was described as an "uphill battle" for Gray. Gray won the Democratic nomination for the U.S. Senate in Kentucky on May 17, 2016. On November 8, 2016, Paul defeated Gray 57% to 43%.
U.S. House campaign On December 5, 2017, Gray announced that he would run for the
United States House of Representatives, entering the Democratic primary for
Kentucky's 6th congressional district. He was defeated in the May 22, 2018 Democratic primary by
Amy McGrath.
Kentucky Secretary of Transportation On December 2, 2019, Kentucky governor-elect
Andy Beshear, announced in a news conference that Gray would be appointed as
Kentucky Secretary of Transportation. Gray was sworn in on December 10. On April 14, 2026, Beshear announced that Gray would be replaced as secretary by Rebecca Goodman. ==Personal life==