Benson served as a Fellow at the Georgetown Institute of Politics and Public Service during the spring 2021 academic semester.

He also interned for two summers at Fox News, working primarily with Hannity & Colmes, before assisting the channel with its coverage of the 2004 Republican National Convention.

[8] After graduating with honors from the Medill School of Journalism at Northwestern University in 2007, Benson served as the producer of The Sandy Rios Show, then a local afternoon radio show with Christian Right commentator Sandy Rios on WYLL-AM in Chicago.

He previously wrote at Andrew Breitbart's "Big" sites and National Review Online's Media Blog.

In August, after the Obama campaign attacked WGN radio in Chicago for allowing Stanley Kurtz to appear on their station, Benson—who was in studio during the interview—detailed his experience.

[14] Then, two weeks before Election Day, Benson joined with Mary Katharine Ham and Ed Morrissey to pen "The Comprehensive Argument Against Barack Obama," released on Hot Air.