ELECTION 2026 – Party Flipper Art Shepherd Makes Another Go for St. Mary’s County Commissioner Seat After Retiring as County Department Head

ELECTION 2026 – Party Flipper Art Shepherd Makes Another Go for St. Mary’s County Commissioner Seat After Retiring as County Department Head

Art Shepherd, who recently switched political parties after running for St. Mary’s County Commissioner in 2010 as a Democrat, filed on June 9, 2025, for the same seat representing Leonardtown and Hollywood on the commissioner board, as a Republican. Shepherd has been requested to participate in an interview, which will be made available to our readers for their benefit in gaining a deeper understanding of those who seek elective office.

ART SHEPHERD A NO-SHOW FOR INTERVIEW

Shepherd cancelled his interview an hour before it was scheduled on Friday the 13th (lucky Art), thereby ducking the chance to answer questions about why he fled the Democratic Party and how he would support more growth in St. Mary’s County smartly.

Shepherd ran for St. Mary’s Commissioner in 2010, losing the election to Republican Dan Morris. Morris declined to become a fixture in Leonardtown and decided that one term was enough. In 2014, Mike Hewitt, a former Democrat who lost his bid for the Democratic nomination for St. Mary’s Commissioner President in 2006 to Francis Jack Russell, ran to replace Morris and won. Hewitt served as the campaign treasurer for St. Mary’s Commissioner President Julie Randall, a Democrat, in 1998 and again for her unsuccessful reelection bid in 2002, when she lost to Republican Tommy McKay.
Commissioner Mike Hewitt decided that, unlike Morris, he liked to hang around in Leonardtown and went on to win two more elections in 2018 and 2022 as a St. Mary’s Commissioner until he has now been term-limited and the voters are forced to find someone else to represent them. 
Hewitt is reported to be advising politicians around St. Mary’s that he will run against the popular conservative incumbent, Delegate Matt Morgan (R-District 29A). 

Shepherd posted the following on his campaign Facebook page:

I am excited to officially announce my candidacy for St. Mary’s County Commissioner for District 2!  I’m a lifelong resident of The County, and I worked with the Department of Recreation and Parks for 40 years.  During this time, I witnessed incredible growth and changes in the fabric of the community.  Public recreation and parks provided me with numerous leadership opportunities that required integrity and sound judgment.  Significant experience was gained through developing budgets, seeking citizen input, and working with the current Board of Commissioners on initiatives and goals. 

As a Republican, I strongly believe that I am now ready to serve our County in a new way – as a dynamic leader focusing on responsible growth, strategic planning, and a conservative fiscal approach.

On June 30th, ArthurShepherd.com will go live! It will provide you with in-depth content regarding the following issues:

• Smart Growth and Infrastructure

• Public Safety

• Fiscal Responsibility: General Fund, Capital, and Enterprise

Fund Budgets that Avoid Tax Increases

• Education & Workforce Development

• Parks, Programs, and Facilities

• Community Wellness