Cheshire is in his sixth season of professional baseball, and second of independent professional baseball. In his MiLB career, Cheshire is 15-5 with a 2.49 ERA in 88 appearances and one start. He originally spent two seasons in the Toronto Blue Jays organization after he was drafted in the 36th round of the 2017 MLB Draft out of Davenport University. He was released by Toronto in 2019 before signing with Brett Jodie and the Somerset Patriots of the Atlantic League. He went 0-1 with a 0.55 ERA in 15 appearances before he was signed by the Twins organization, and he spent two seasons with the Twins organization.