Less than an hour into Maggie Rogers’ sold-out show Sunday in Maryland, the Grammy-nominated singer-songwriter brought out a surprising special guest onstage: Gov. Wes Moore.

The Democrat, dressed in blue jeans and a black t-shirt with the slogan “Maryland Tough, Baltimore Strong,” was greeted with an ear-shattering round of applause from the 20,000 concertgoers—an acclamation that only grew when Moore proclaimed June 16 as “Maggie Rogers Day” in the state.

Hours later, Moore made another—starkly different—announcement when he signed an executive order pardoning more than 175,000 marijuana-related convictions in one of the largest-ever acts of clemency involving low-level drug offenses.

“We're taking actions that are intentional that are sweeping and unapologetic,” Moore said at a Monday morning press conference. “But there's a reason that we're being so intentional today. Policymaking is powerful.”

For most first-term governors, the dual headline-making moments seem like an impressive political feat. But for Moore, an Army veteran who once led the largest anti-poverty non-profit in the country, it is the latest in a series of bold moves that have pushed him into the national—and even presidential—conversation.

Kaye Wise Whitehead, a professor of communication and African American studies at Loyola University Maryland, told The Daily Beast that Moore has three qualities she........

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