The president's signature achievement has been the Affordable Care Act, more commonly known as Obamacare. To Obama's GOP foes, the program is tantamount to evil. Repealing it would have been President Cruz's top priority. But progressives generally see it as a win, though Bill Press is here to rain on the victory parade. To him, Obamacare is a compromised, Heritage Foundation-inspired retread that fails to achieve progressive goals: "It's a half-baked measure that falls short of what is needed and of what was politically possible. Its main provision is to force people to buy health insurance from a private insurer if they're not already insured by their employer. That is certainly not a progressive idea. In fact, its not even a good conservative idea."

While Press nails the act's shortcomings, he doesn't make the case that more was achievable and he doesn't give sufficient weight to the problem of Joe Lieberman as one of the Democrats' 60 Senate votes needed to break a Republican filibuster.

The single issue that most helped to propel Barack Obama past Hillary Clinton in 2008 was his opposition to the invasion of Iraq, which contrasted sharply with Clinton's vote to authorize the war. By 2008, the phrase "Iraq War" was shorthand not only for the disastrous invasion itself, but also for the campaign of lies and half-truths (remember the phrases "smoking gun" and "mushroom cloud"?) used to sell it, the use of torture, and the surveillance state built to contain the constant threat of terror in the United States that the war was supposed to alleviate.

Barack Obama was dealt a very weak hand from the preceding Bush administration on foreign policy. He played it poorly from the outset by arguing that the "real war" was in Afghanistan instead of Iraq. That might have at one time been true, but by 2009, that was a difficult case to make--and our time there since 2009 has accomplished little. Press writes that "with the Taliban still controlling vast areas of Afghanistan and with no guarantee that any central government ... will survive, many Americans are wondering why we went there in the first place, what we achieved in the long run, and why we stayed so long. President Obama could have pulled the plug on Afghanistan [during] his first month in office. The end result would have been the same." Press is also critical of Obama's war in Libya, which was fought absent congressional support, and that accomplished little more than turning the country into a failed state.