Milbank was born to a Jewish family, the son of Ann C. and Mark A. Milbank. He is a graduate of Yale University, where he was a member of Trumbull College, the Progressive Party of the Yale Political Union and the secret society Skull and Bones. He is a graduate of Sanford H. Calhoun High School in Merrick, New York. In 1993, Milbank married Donna Lynn DePasquale in an interfaith Jewish and Roman Catholic ceremony. That marriage ended in divorce. In 2017, Milbank married Anna Greenberg.
Milbank covered the 2000 and the 2004 presidential elections. He also covered President George W. Bush's first term in office. After Bush won the 2000 election, Karl Rove asked the Washington Post not to assign Milbank to cover White House news. In 2001, a pool report penned by Milbank which covered a Bush visit to the U.S. Capitol generated controversy within conservative circles. According to Milbank, the nickname given to him by the president is "not printable in a family publication."
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.
Milbank was criticized for a July 30, 2008 article in which, in part by using snippets of quotations, he portrayed Barack Obama as being presumptuous. A few days later MSNBC's Keith Olbermann stated that Milbank would not be allowed back onto his show, which Milbank had appeared on since 2004, until Milbank submitted "a correction or an explanation." However, Milbank had apparently already left Olbermann's show for another show on CNN. Milbank stated that he has been dissatisfied since he was criticized by Olbermann's staff over making a positive comment about Charlie Black, a McCain senior advisor, and as a result had already been negotiating with CNN.
Milbank and Chris Cillizza appeared in a series of humor videos called "Mouthpiece Theater" which appeared on the Washington Post's website. An outcry followed a video in which, during a discussion of the White House "Beer Summit", they chose new brands for a number of people, including "Mad Bitch Beer" for Hillary Clinton. Both men apologized for the video and the series was canceled.
In 2011, Milbank was the subject of street art featuring his likeness and last name.
Milbank is the author of Smash Mouth: Two Years in the Gutter with Al Gore and George W. Bush—Notes from the 2000 Campaign Trail.
Homo Politicus: The Strange and Scary Tribes that Run Our Government was published by Random House in January 2008.
In 2010, Doubleday released Milbank's polemic biography of conservative pundit Glenn Beck: Tears of a Clown: Glenn Beck and the Tea Bagging of America, which a review in Milbank's paper, the Washington Post, said was a "droll, take-no-prisoners account of the nation's most audacious conspiracy-spinner."
Milbank has stated that his "policy" on presidential general elections is to vote for the best candidate who is not on the ballot. He voted for John McCain in 2000, Chuck Hagel in 2004, and Michael Bloomberg in 2008. He has explained that his approach allows him to "go through the exercise of who would be a good president" while avoiding committing to one candidate or another in the race.
Greg Marx, associate editor of the Columbia Journalism Review, describes Milibank as "extravagantly contrarian." Marx and New York University journalism professor Jay Rosen have critiqued what they view as "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."
Milibank has criticized the growth of the White House Correspondents' Dinner, writing in 2011 that the event "was a minor annoyance for years, when it was a 'nerd prom' for journalists and a few minor celebrities. But, as with so much else in this town, the event has spun out of control. Now, awash in lobbyist and corporate money, it is another display of Washington's excesses."
Revealed through the second Wikileaks release on the DNC, Dana Milbank appears to have asked the Democratic National Committee (DNC) to do the majority of the research for a negative column he wrote about Donald Trump in April 2016.
In the Washington Post, Milbank, who is Jewish, called Trump's Jewish staffers "Shanda" for not resigning. LINK: https://www.washingtonpost.com/opinions/the-trump-administrations-three-court-jews-disgrace-themselves/2017/08/18/929a68b4-840c-11e7-ab27-1a21a8e006ab_story.html