Unlike Kennedy and Johnson, Obama was very much the technocrat-in-chief, setting the tone for the people he would surround himself with. His intelligence was generally in little doubt. During his eight years in the Oval Office, the president was an almost unbelievably voracious reader, devoting around an hour on most days to books of history, philosophy, biography, or even sci-fi novels. But being smart and well-read doesn’t necessarily lead to good judgment or bold vision; in some cases, even, the former can undermine the latter.

“The best and the brightest” entered the American lexicon, with more than a hint of irony, through David Halberstam’s landmark book on the men who dragged America into the Vietnam War. In his foreword to the book, Senator John McCain writes of these men: “They misjudged the world. And, most of all, they misjudged themselves.”

Matters of judgment still loom large four decades later. I, or any critic of Obama’s foreign policy, could sit with an Obama administration official, and, even if we agreed on all the facts and specifics of a particular country or conflict, it wouldn’t matter much. Divergences in how people interpret Obama’s legacy have much more to do with fundamentally different starting assumptions about America’s role in the world and even human nature—in other words, the very reasons why we do what we do. In fact, looking back at my own meetings with officials during the Obama era, rarely do I ever recall hearing something and thinking to myself that I had just heard some gross error of fact. This is why I found such meetings so frustrating and circular: The only things we disagreed on were the most important.

For example, I have little disagreement with the technical aspects of the Iran nuclear deal. The problem, well before negotiations even started, was the initial decision to treat Iran’s nuclear program as the top U.S. priority in the Middle East. On Syria, opponents of intervention against the Assad regime would often claim that various military options were prohibitively difficult to implement, and that those who claimed otherwise weren’t military experts. Of course, Obama himself is not a military expert either. Either way, the claim was disingenuous: Senior military officials had readied a military response to Assad’s violation of the “red line” drawn over the use of chemical weapons in August 2013, and with no notable dissent. Ultimately, the divide over Syria was about deeper questions of moral responsibility, America’s role in the world, and whether an intervention would be “worth” the cost (something which, of course, can’t actually be measured). As Steven A. Cook wrote in early 2012 when only around 7,000 people had been killed in Syria: “Is it a morally superior position to sit by as people are being killed rather than take action that will kill people, but nevertheless may end up saving lives as well?”