Hillyer was born and raised in New Orleans and graduated from the Isidore Newman School in 1982 before matriculating at Georgetown University, where he graduated with an A.B. in government and theology (cum laude) in 1986. While at Georgetown, Hillyer held major editorial positions at the student newspaper, The Hoya, and wrote extensively during the school’s Final Four basketball appearances in 1984 and 1985.

After his graduation, Hillyer joined the New Orleans Times-Picayune as a correspondent before serving a term as research/issues director for the Louisiana gubernatorial campaign of U.S. Representative Bob Livingston in 1987. He served as an unpaid director in the state campaign for Pete Dupont’s 1988 GOP presidential bid. A former page at the 1980 Republican National Convention, Hillyer attended the 1988 Republican convention as an alternate delegate from the state of Louisiana.

In 1989, Hillyer became managing editor of Gambit, a weekly news magazine in the New Orleans area. He later joined Congressman Livingston’s staff, rising to the position of press secretary.

After the 1996 elections, Hillyer returned to journalism and political commentary. In 1997, he joined the editorial staff of the Arkansas Democrat-Gazette, focusing on both local and national issues during the term of then-governor Mike Huckabee. In 1998, Hillyer joined the editorial desk at the Mobile Register, gaining widespread acclaim for his coverage of statewide politics and its effect on the city as a whole, receiving the Carmage Walls Commentary Award from the Southern Newspaper Publishers Association and the Green Eyeshade Award for commentary from the Society of Professional Journalists.

In 2006, Hillyer returned to Washington. He served as a managing director at Qorvis Communications and executive editor of The American Spectator before assuming the post of associate editorial-page editor at The Washington Examiner. From 2009 through 2011, he was a senior editorial writer at the Washington Times. He is currently a senior editor and columnist at the Spectator.

Hillyer’s articles have appeared in many publications, including National Review, the Wall Street Journal, the Washington Post, the New Republic, The Guardian (UK), and Investor’s Business Daily. His television appearances have included Fox News, MSNBC, and CNN.

On May 23, 2013, six-term Republican U.S. Representative Jo Bonner announced he would resign from Congress effective August 15, 2013, to become a vice chancellor at the University of Alabama. Hillyer made his announcement to seek the Republican nomination for Bonner’s seat one day later, telling his audience at the American Spectator: “I am a constitutional conservative, and an ‘opportunity society’ conservative as well, hearkening back to the Reagan-Kemp era of prosperity and liberty. Free men and women, with free minds, in a free market, produce abundance and a vibrant society.”

Hillyer received outside support from Rick Santorum, who recorded a radio ad purchased by Citizens United Political Victory Fund. He also garnered the endorsement of Citizens for the Republic, the former Ronald W. Reagan political-action committee based in Alexandria, Virginia.