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He endorsed Democratic candidate Hillary Clinton in the run-up for the 2016 U.S. presidential election.

Since the Reagan years, Republicans routinely speak in broad themes and tend to blur the details, while Democrats typically ignore broad themes and focus on details. Republicans, for example, speak constantly of "liberty" and "freedom" and couch practically all their initiatives—tax cuts, deregulation, and so forth—within these large categories. Democrats, on the other hand, talk more about specific programs and policies and steer clear of big themes....What Democrats have typically not done well since Reagan's time is connect their policies to their larger beliefs. In fact they have usually tried to hide those beliefs, or change the conversation when the subject arose. The result has been that for many years Republicans have been able to present their philosophy as somehow truly "American", while attacking the Democratic belief system as contrary to American values.

Tomasky was born and raised in Morgantown, West Virginia, the son of Maria (Aluisi) and Michael Tomasky, a trial attorney. He is of Serbian and Italian descent. He attended West Virginia University as an undergraduate and then studied political science in graduate school at New York University. His work has also appeared in The New York Times Book Review, The Washington Post, Harper's Weekly, The Nation, The Village Voice, The New York Review of Books, Dissent, Lingua Franca, George, and GQ. He lives with his wife Sarah and daughter (Margot Julianna Kerr Tomasky, born July 6, 2010) in Silver Spring, Maryland.

In an October 2010 essay, "The Elections: How Bad for Democrats?", Tomasky gives his "own answer to the question of how things got this bad", expounding a theme he had been developing for several years in other articles:

From 1995 to 2002, Tomasky was a columnist at New York magazine, where he wrote the "City Politic" column. He was later executive editor of liberal magazine The American Prospect, and remains a contributing editor. On October 23, 2007, Guardian America was launched with Tomasky as its editor. On March 3, 2009 he replaced Kenneth Baer as editor of U.S. political journal Democracy, at which time his title at The Guardian changed to editor-at-large. In May 2011 Tomasky left The Guardian to join Newsweek / The Daily Beast as a special correspondent.

Tomasky is the author of Left for Dead: The Life, Death, and Possible Resurrection of Progressive Politics in America (1996), and of Hillary's Turn: Inside Her Improbable, Victorious Senate Campaign (2001), a chronicle of Hillary Clinton's successful election to the Senate in 2000.

Michael John Tomasky (born October 13, 1960) is an American columnist, commentator, journalist and author. He is the editor in chief of Democracy, a special correspondent for Newsweek / The Daily Beast, a contributing editor for The American Prospect, and a contributor to The New York Review of Books.