Bennett has covered six presidential elections and reported from the White House under three administrations. His exclusive interviews – spanning cultural icons, world leaders, and groundbreaking artists – have drawn wide national attention.

His work with the PBS News Hour team has earned a succession of honors: a Peabody Award in 2024 for coverage of the Israel–Hamas war; a Walter Cronkite Award for Excellence in Journalism in 2025 for the On Democracy series; and a second Peabody Award in 2026 for the program's examination of President Trump's sweeping immigration policy changes during the first year of his second term.

Bennett joined PBS in 2021 from NBC News, where he served as White House correspondent and frequent MSNBC anchor. At NBC, he was part of the team recognized with the 2022 Edward R. Murrow Award for Overall Excellence. His broader broadcast footprint includes appearances as a political analyst on ABC News, CBS News, and NPR, as well as a tenure hosting C-SPAN's Washington Journal. He launched his journalism career at ABC News' World News Tonight with Peter Jennings, following his graduation from Morehouse College.

Committed to expanding opportunity in the field, Bennett established a scholarship at Morehouse for English and journalism majors. He also serves on the Board of Trustees of the Colonial Williamsburg Foundation, the nation's largest living history museum.

In March 2026, Bennett published his debut book, Black Out Loud: The Revolutionary History of Black Comedy from Vaudeville to '90s Sitcoms (HarperCollins), an instant bestseller. The book offers a deeply researched exploration of the evolution and cultural impact of Black comedy in America.

He lives in the Washington, DC, area with his wife and their son.