Kondracke worked for several major publications, serving for twenty years as executive editor and columnist for the non-partisan Capitol Hill newspaper Roll Call.
After quitting the Army in 1963, Kondracke joined the staff of the Chicago Sun-Times, transferring to the paper's Washington bureau in 1968, eventually becoming White House correspondent in 1974.
In the meantime, his increasing renown resulted in his becoming a commentator for National Public Radio, This Week with David Brinkley and The Wall Street Journal.
[citation needed] For the US's 1984 presidential election, he was a panelist for the second televised debate (concerning foreign policy) between President Ronald Reagan and Democratic challenger Walter Mondale.
During this time he wrote a twice-weekly column for Roll Call ("Pennsylvania Avenue") that was syndicated by Newspaper Enterprise Association, part of United Media.
[10] In October 1998, Kondracke began co-hosting his own television series, The Beltway Boys, with Fred Barnes, for the Fox News Channel.
Kondracke was the Jack Kemp Professor of Political Economy in the John W. Kluge Center at the Library of Congress from September 2011 to June 2012, where he researched and wrote about "the late Jack Kemp's congressional career, his leadership role during the Reagan Era, his presidential campaign and his influence on the Republican Party and the nation".
[13] For his correct prediction of the Democratic takeover of Congress he won The Washington Post's Crystal Ball Tournament of Champions Award in 2006.
The book was the basis of a CBS television movie named Saving Milly, featuring Madeleine Stowe and Bruce Greenwood, which was broadcast on March 13, 2005.