It's very hard to strike the right balance in such a piece.
On the one hand, I firmly believe that Obama is one of the most successful presidents in my lifetime. On the other hand, Obama set out to be something far more significant than that-- a truly transformational president (or, in Stephen Skowronek's terms, a reconstructive president). On that score, Obama failed, for reasons I describe in the piece. We are still living in the Reagan regime.
Obama's failure at the latter goal, however, should not detract from what was, all things considered, a very successful presidency. Not every president-- even the most successful--is destined to be a Lincoln or an FDR. And, over time, I predict, Obama's reputation will only grow, especially among the people who were his political opponents today.
Near the end of the piece I point out how much turns on whether Hillary Clinton or Donald Trump succeeded Obama. And I note that even though Clinton lost a very close election, which could easily have gone the other way, that fact won't do Obama very much good.
Nevertheless, I close by pointing out that Obama probably created a space for the next Democratic president to be a truly transformational figure, if he or she can rise to the challenge:
[I]f Hillary Clinton had succeeded Obama, his prospects as a reconstructive leader would look far brighter. It is hard for a party to win the presidency three times running; achieving this usually signifies a political party’s dominance. Conversely, there are no cases of reconstructive presidencies (Jefferson, Jackson, Lincoln, FDR, Reagan) in which the other party regained the White House after two terms.Clinton lost several key states by the closest of margins, and if only a few things had been different, the result could easily have gone the other way. But in constructing a president’s legacy, close doesn’t count. Because the Republicans eked out a victory, Obama won’t get the benefit of a Democratic successor to protect his accomplishments. Instead, Republicans will control the White House and both houses of Congress; they will have four years to push their programs, issue new regulations, and appoint scores of life-tenured federal judges. For better or worse, Donald Trump’s excruciatingly narrow win means that we still live in a Republican-dominated political world.
All is not lost for Democrats, however. Obama may not have dismantled the Republican fortress, but he put serious cracks in it. History suggests that Donald Trump, for all his bluster, heads a seriously weakened coalition and a deeply fractious party. All the signs point to Trump being a disjunctive leader like Hoover or Carter — arriving at the tail end of the Reagan regime. When such presidents fail, the opposition party is poised to begin a new era of politics. Obama took the Democrats to the edge of the Promised Land; the next Democratic president may be able to bring them across the river Jordan.