[1] On January 17, 2023, Governor-elect Wes Moore nominated Day to serve as the Maryland Secretary of Housing and Community Development.

[7] He ran on a platform that included improving the city's infrastructure, attracting economic growth through business-first initiatives, and creating jobs.

[28] In March 2019, Day adopted the Vision Zero policy, which sought to eliminate all pedestrian deaths and serious injuries caused by vehicles by January 2030.

[13] In June 2021, Day announced a collaboration between Salisbury and Bird, which debuted rentable electric scooters in the city, replacing the previous Spin bikes.

[37][39] In April 2021, Day was named in a report from the Maryland National Guard Bureau Office of Equity and Inclusion, in which he was accused of receiving and not forwarding reports of discrimination against Sergeant Bruce Weaver, a Black soldier who alleges that his all-white trainers forced him to wear a chain, representing the "chain of command" during training at the Delaware Army National Guard officer candidate school, in 2015.

The Maryland National Guard exonerated its personnel after multiple internal investigations and appealed the bureau's decision.

[40] Day rejected any association with the claims, releasing a statement on social media saying "I am pained to have my name spoken in relation to the 2015 incident I was not even present to witness".

[41] On January 17, 2023, Governor-elect Wes Moore nominated Day to serve as the Maryland Secretary of Housing and Community Development.

[44] During the 2024 legislative session, Day testified on the Moore administration's bills to increase federal funding and reducing barriers for affordable housing projects in the state, especially those around commuter rail stations, as well as legislation establishing a "Tenant's Bill of Rights" and providing additional protections to renters against evictions.

[4][5] In April 2017, Day said he opposed the Trump administration's decision to cut funding toward Chesapeake Bay cleanup programs from the federal budget.

[51] In November 2022, Day signed into law a city ordinance that would ban plastic bags in retail stores and restaurants.

[55] The district map, which was supported by the American Civil Liberties Union of Maryland and the Wicomico County NAACP, was adopted by the Salisbury city council by a 4–1 vote in September 2014.

[57] In June 2017, Day called for the removal of a memorial of Confederate general John Henry Winder from the lawn of the old Wicomico County courthouse in Salisbury.

[63] In November 2019, Day endorsed South Bend mayor Pete Buttigieg in the 2020 Democratic Party presidential primaries.