[2] Chestek first ran for the Wyoming House of Representatives in 2016 when incumbent Republican representative Glenn Moniz of the 46th district retired to run for the state senate.
He won the Democratic primary unopposed, but was defeated in the general election by Bill Haley, receiving 42% of the vote.
[3] When incumbent Democrat and House Minority Leader Cathy Connolly declined to run for reelection, Chestek announced his candidacy and won the Democratic primary on August 16, 2022, unopposed.
[4] He then won the general election on November 8, 2022, defeating Republican nominee Wayne Pinch with 60% of the vote.
[5] In 2024, Chestek ran for re-election again Republican Shane Swett.