Shermichael Singleton is a nationally recognized conservative on CNN Political Commentator. He’s also a political strategist, writer, and media entrepreneur with a distinguished career that spans politics, broadcast journalism, and digital media innovation.
A native of New Orleans, Louisiana, Singleton relocated to Dallas, Texas, at the age of 10, where his passion for politics was sparked at a young age. He went on to study at Morehouse College, the nation’s only historically Black all-male college, earning a Bachelor’s degree in Political Science.
His career in politics is marked by high-level involvement in several presidential campaigns, including those of Newt Gingrich, Mitt Romney, and Dr. Ben Carson. Over the years, Singleton has served as a strategic consultant for a wide range of political candidates at the federal, state, and local levels. He sharpened his analytical and communications skills while working at America Rising, a prominent Republican opposition research firm. His insight and commentary have been sought across major media platforms including CNN, Fox News, NewsNation, BBC, MSNBC, CBS, Politico, The New York Times,The Wall Street Journal, The Washington Post, BuzzFeed, The Huffington Post, BET, and C-SPAN to name a few.
Singleton was one of only ten African Americans appointed to the federal government’s Senior Executive Service (SES) during the first Trump administration, and he holds the distinction of being the youngest individual ever appointed to an SES position within the U.S. Department of Housing and Urban Development, where he served as Deputy Chief of Staff.
A pioneering voice in the evolution of digital media, Singleton co-hosted Consider It, a Facebook (Meta) and Vox Media joint venture focused on culture and politics. In 2022, he co-created and hosted Screen Share on MSNBC’s Peacock platform, under MSNBC’s Special Projects Division. The show served as the only show hosted by a conservative, we’re Singleton would debate liberal guests about culture and politics. He has also served as a guest host on several shows, and has anchored the widely viewed digital news show Rising under Nexstar’s The Hill.
As a political writer, Singleton has penned columns for The Hill, The Boston Globe, The Washington Post, and U.S. News—offering deeply analytical and thought-provoking commentary on national affairs. He also hosted a weekly nationally syndicated radio program on SiriusXM’s Urban View, engaging hundreds of thousands of listeners weekly.
Singleton is the co-founder and co-owner of We The Free TV, a bold new independent media network focused on firearms and freedom-centric storytelling. Based in Washington, D.C., We The Free TV produces a diverse slate of programming ranging from action-driven reality series and firearms shows (educational and entertainment) to family entertainment and political/cultural commentary. The network aims to amplify voices often underrepresented in mainstream media while cultivating original content for digital audiences.
In addition to his expansive political and media work, Singleton is a passionate advocate for responsible gun ownership. He co-owns Guns Out TV, a YouTube series he co-created to spotlight gun ownership, firearms safety, and education in America.
Outside his professional life, Singleton is a man of deep artistic and intellectual passions. A trumpet player, pianist, and drummer— he finds inspiration in jazz and classical music. He is also a visual artist who enjoys painting and drawing, and an avid motorcycle enthusiast who participates in track days riding one of his Ducati motorcycles. He’s also an avid competitive shooter and hunter. His adventurous spirit and love for learning are integral to his dynamic personality.
Shermichael Singleton’s life and work reflect a steadfast commitment to political thought, cultural innovation, and personal excellence. Through his endeavors in media, politics, and entrepreneurship, he continues to shape national conversations and build platforms that challenge, inform, and inspire.
