After working for two local banks in Tennessee, he transitioned into a position where he writes and researches grants for Trezevant Manor, a senior living facility in Memphis where his father is a member of the Board.
In 2023, Gillespie supported a resolution to expel two of three Democratic lawmakers from the legislature for violating decorum rules.
[2] Running in a contested primary election on August 6, 2020, Gillespie received the Republican Nomination for Representative of the 97th House District when he defeated Brandon Weise 78.3% (3,626 votes) to 21.7% (1,007 votes).
His father is on the Board of Trezevant Manor in Memphis where Gillespie was working at the time of his election to the Tennessee House of Representatives.
A graduate of High Point University in North Carolina, he earned a Bachelor of Arts degree in Political Science.