After Bush won the 2000 election, Karl Rove asked The Washington Post not to assign Milbank to cover White House news.

[7] In 2001, a pool report penned by Milbank which covered a Bush visit to the U.S. Capitol generated controversy within conservative circles.

"[9] Milbank writes "Washington Sketch" for the Post, an observational column about political theater in the White House, Congress, and elsewhere in the capital.

Before coming to the Post as a political writer in 2000, he covered the Clinton White House for The New Republic and Congress for The Wall Street Journal.

[14] Milbank stated that he has been dissatisfied since he was criticized by Olbermann's staff over making a positive comment about Charlie Black, a John McCain senior advisor, and as a result had already been negotiating with CNN.

[16] In a December 4, 2021 Op-ed, Milbank wrote that overall US media sentiment for President Joe Biden is as bad as, if not worse than, it was for then-President Donald Trump.

He used data from the analytics company Forge.ai to mine through more than 200,000 articles from 65 different news sources to create a "sentiment analysis" of pro or con coverage.

[25] New York University journalism professor Jay Rosen wrote of "Milbank's insistence on characterizing political debate as consisting of two unreasonable poles, and himself as a truth-teller caught in the middle — a posture so habitual and inflexible that it has become an ideology".