[4] Hershey worked as a vice president for project management for the Trammell Crow Company from 1993 to 2003, afterwards serving as a member of the Queen Anne's County Economic Development Commission until 2006.

[1] That year, he unsuccessfully ran for the Queen Anne's County Board of Commissioners in District 2,[5] losing to Rodney Niedomanski in the Republican primary.

[8] He won the Republican primary in September 2010, edging out Sossi by 124 votes, or a margin of 1.2 percent,[9] and ran unopposed in the general election.

[11] The Republican Central Committees of Caroline and Kent counties voted to nominate him, while the Queen Anne's and Cecil County Republican Central Committees voted to nominate his opponent, Michael D. Smigiel Sr.[12] In September, Governor Martin O'Malley appointed Hershey to the seat over Smigiel,[13] and he was sworn in on October 1.

[19] Hershey ran for a full four-year term in 2014, during which he faced a primary challenge from former state delegate Richard Sossi, whom he defeated with 56 percent of the vote.

[29][30] He also opposes the Blueprint for Maryland's Future[31] and has proposed cutting back spending on the education reform package so that the state only focuses on its most important components.

[32] During his 2002 commissioner campaign, Hershey proposed providing tax credits and improving benefits to retain teachers in the county.

[33] During the 2013 legislative session, Hershey introduced a bill to extend voting rights to the student member of the Kent County Board of Education.

[42] In February 2025, amid rising utility rates, Hershey suggested that Maryland increase its natural gas generation and repeal the state's ban on fracking.

[45] During the 2016 legislative session, Hershey supported a measure to provide tax breaks to households that earn more than $150,000 annually, which he claimed represented the state's small business owners.

[48] In May 2020, amid the COVID-19 pandemic, Hershey called on the Maryland Board of Public Works to freeze the minimum wage at $11 an hour for two years.

[52] During the 2018 legislative session and following the 2017 Las Vegas shooting, Hershey was one of three Republicans to vote for a bill to ban bump stocks in Maryland.

[53] In 2019, Hershey voted against a bill to abolish the state's Handgun Permit Review Board, which handled conceal carry applications.

[68] He opposed impeaching and removing Trump following the January 6 United States Capitol attack, saying it would "undermine the efforts to ensure a peaceful transfer of power".

[69] During the 2017 legislative session, Hershey voted against a bill that would give the attorney general of Maryland the power to pursue cases against the federal government.

He also expressed support for a primary challenge against Ohio state legislator Candice Keller after she claimed that the 2019 Dayton shooting was caused by "drag queen advocates".

[79] In 2023, he criticized a bill creating a statewide referendum on codifying Roe v. Wade into the Constitution of Maryland,[56] calling it "performative progressivism".

[80] In October 2010, Hershey criticized the state's public transportation system, arguing that private industry would "manage and provide this service more cost efficiently than the government".

[25] In June 2015, Hershey said he supported Governor Larry Hogan's decision to shift funding for the Red Line toward road widening projects in other jurisdictions around the state, especially Route 404.