Obama has screwed up plenty of things himself, most notably his doomed strategy of trying to secure a deficit agreement in 2011, his failure to keep pressing on financial reform, and his broad acceptanceof the Bush administration’s civil liberties rollback.Later he goes on to compare Obama favorably with Kennedy
Kennedy campaigned on liberal priorities like federal aid for education and health care for the elderly, but found his agenda bottled up by conservative southern Democrats in Congress. Calvin MacKenzie and Robert Weisbrot, in their book The Liberal Hour, detail the tortured, arms-length relationship between the civil rights movement and Kennedy, who supported integration but need segregationist support to move his domestic agenda. Kennedy had promised during the campaign to end housing segregation “with the stroke of a pen,” but reneged, prompting activists to mail pens to the White House. He nominated segregationist judges and had a busload of Freedom Riders arrested (as a compromise, to keep them from being lynched), and met with civil rights activists who “scorched [him] with anger.” After his assassination, Americans came to look back on Kennedy’s presidency through a golden-hued nostalgia, which is what allows writers like Harris and Martin to present Kennedy as a glamorous poet-king who represented something larger than the pedestrian struggles that actually consumed his presidency.
I notice you didn't discuss Kennedy's legislative successes. Or rather I think you discussed all of them and there weren't any (I don't remember clearly I wasn't even born when he was elected). Also what about the Bay of Pigs ? And sending "military advisers" to fight in Vietnam ? There is no comparison.
On the other hand, I'm not sure I agree with 2 of your criticisms of Obama. You criticize him for not pressing on financial reform and praise him for signing a major financial reform bill (the first in decades which did not consist of reforming regulation by gutting it). Could more have been obtained ? I mean financiers are rich and politicians like campaign donations. The outcome was much less than we need but much more than could be reasonably hoped.
On the 2011 negotiations first not so much harm was done as the Republicans said no. I would like to believe, and sometimes convince myself, that this was Obama's plan. The result is that it is almost impossible for very serious centrists to deny that the Republicans are rigid fanatics with whom no compromise is possible (N Ornstein is as very serious as a centrist gets and works at AEI). My hope was that Obama was securing his base among the well informed commentariate and that he would then move on to win the swing undecideds with a bit of populism (egalitarianism is very very popular). This is what he has done (OK with a very very little bit of populism). Reducing the harping from the very serious centrists who wish he would just try to compromise is worth something. I (sometimes) think it was an OK 11 dimensional chess move.