Greenwald frequently criticizes those on both ends of the conventional left-right political spectrum. In fact, he is generally most critical of actions that have the support of both liberals and conservatives, since "the worst and most tyrannical government actions in Washington are equally supported on a fully bipartisan basis."[22]
In the preface to his first book, How Would a Patriot Act? (2006), Greenwald begins by giving some of his own personal political history, describing himself as at first neither liberal nor conservative but as one who had taken positions that can be ascribed to both liberals and conservatives, voting neither for George W. Bush nor for any of his rivals, indeed not voting at all.[23] Bush's ascendancy to the U.S. Presidency "changed" Greenwald's previous uninvolved political attitude toward the electoral process "completely":
Over the past five years, a creeping extremism has taken hold of our federal government, and it is threatening to radically alter our system of government and who we are as a nation. This extremism is neither conservative nor liberal in nature, but is instead driven by theories of unlimited presidential power that are wholly alien, and antithetical, to the core political values that have governed this country since its founding"; for, "the fact that this seizure of ever-expanding presidential power is largely justified through endless, rank fear-mongering—fear of terrorists, specifically—means that not only our system of government is radically changing, but so, too, are our national character, our national identity, and what it means to be American."[23]
Believing that "It is incumbent upon all Americans who believe in that system, bequeathed to us by the founders, to defend it when it is under assault and in jeopardy. And today it is," he stresses: "I did not arrive at these conclusions eagerly or because I was predisposed by any previous partisan viewpoint. Quite the contrary."[23]
Ostensibly resistant to applying ideological labels to himself, he emphasizes repeatedly that he is a strong advocate for U.S. constitutional "balance of powers"[9] and for constitutionally-protected civil and political rights in his writings and public appearances.[1]
Throughout them he has relentlessly criticized the policies of the George W. Bush administration and those who support or enable it, arguing that most of the American "Corporate News Media" excuse Bush's policies and echo administration talking points rather than asking hard questions.[19][24]
Entitling his Unclaimed Territory blog entry for January 16, 2006, "Bush Followers Are Not Conservatives," Greenwald explains this position:
It has long been clear that there is nothing remotely "conservative" about this Administration, at least in the sense that conservative ideology has stood for a restrained Federal Government which was to be distrusted. There has been a long line of decidedly un-conservative actions by this Administration – from exploding discretionary domestic spending to record deficits to an emergency convening of the Federal Government to intervene in one woman’s end-of-life decisions to attempts to federalize, even constitutionalize, marriage laws – all of which could not be any more alien to what has been meant by "conservatism" for the past 40 years.[25]
The New York Times describes Greenwald as a liberal.[26][27]
In his various media guest appearances and publications, Greenwald elaborates his political views, which he also summarizes succinctly in responding to "six questions ... about political campaign coverage and the media" that Ken Silverstein posed to him in an article published in Harper's Magazine on February 21, 2008.[19]
Greenwald holds a favourable view of drug liberalization. He conducted research, commissioned by the Cato Institute, on the effect of the abolition of all criminal penalties for personal drug possession in Portugal, which occurred in 2001. According to Greenwald, "decriminalization in Portugal has been a resounding success... It has enabled the Portuguese government to manage and control the drug problem far better than virtually every other Western country does".[28]