It was harder for me at first to grasp the true extent of Obama's failings, but examining some new perspectives has helped to make things a little clearer.
Recently, I've started watching a lot of Jimmy Dore's content on Youtube. Dore is a dyed-in-blue, true-to-the core liberal. I believe he was a Bernie supporter and his politics are indeed far left of center. He is not a fan of Trump and he's also affiliated with The Young Turks and frequently works with them (I believe he was actually there during their election coverage, so if you take a look at the compilation videos showing the Young Turks election day meltdown you should be able to get a glimpse of him).
I was ready to write Dore off the minute I heard he was affiliated with The Young Turks - their bias is legendary, and I just don't expect any degree of rational objectivity when I watch their content (Cenk has a rational moment or two, admittedly - Ana and just about everyone else they bring on is perpetually insufferable). But taking the time to watch him has really changed my mind - he's not like the other Young Turks or most of the typical "I'm With Her" liberals who can't see leftist flaws for the life of them. He notices BS on the left and calls it out regularly.
To this end, Dore absolutely
eviscerates Obama and Clinton on a regular basis, as well as the entirety of the DNC. He calls out all of their hypocrisy and carefully outlines the tendency they and their supporters have to attack Trump for doing/supporting things that they've excused liberals like Obama and Clinton for endorsing for years.
Again, Dore is a far left liberal, but I actually like that about him. It is one thing to hear conservatives critique Obama; it is another entirely to hear comprehensive articulations of Obama's failings from the perspective of someone who is a devoted leftist and ought to be firmly in the Obama camp. I've watched many dozens of Dore's videos so far and they've been eye-opening - I can't find much to disagree with. They show pretty clearly how badly Obama has failed at being what he was actually supposed to be - a progressive liberal. Instead, what he gave us was an individual claiming to be progressive while carrying out contrary policies, and at the same time formenting a partisan culture designed to prop up the myth of his progressivism and shame social conservatism. His governance wasn't great for conservatives and it wasn't great for progressives - I can't even really tell you who he really benefited, except perhaps for committed globalists, SJWs, and warhawks.
What we saw under Obama was an incredible increase in partisan politics - in the last 8 years, the gap between the left and right has widened, and the left has become more regressive, aggressive, intolerant, and hypocritical than it has ever been. I've never seen the country this tense and divided in my lifetime. The decline has been visible, and not even that gradual - it all occurred during Obama's term, and you could really see and feel the change as it happened. Obama not only seemed to tacitly support or encourage these developments (see, for example, his campus sexual assault policies and their well documented negative impacts), but also to embody them. His governance was, in many ways, an exercise in hypocrisy (as Dore's videos will show).
He came as a progressive, but went further right than the conservatives in many ways. He came as a uniter, but has left the nation more divided than ever. He came bringing hope, but now at the end of his presidency it seems the number of hopeless Americans (given the negative direction many of our national socio-economic indicators have been going) has increased. He was supposed to help usher-in a post-racial era that would benefit minorities, but at the end of the 8-years African Americans have regressed on nearly every major socio-economic indicator and have seen the wealth gap between them and other groups increase.
Is he the worst president ever? I don't think so (we've had some pretty poor commanders-in-chief, many of whose names have fallen into historical obscurity for that reason), but the more I truly think about it, the less inclined I am to contend that he was a particularly good president. I'm glad I didn't vote for him in 2012 and I'm glad his hand-picked successor (who would have simply kept his business-as-usual for four more years) was kept out of the White House. I genuinely believe the country will be better for it (hopefully Trump doesn't prove me wrong).
Anyway, here are some of Dore's videos outlining from a liberal perspective just how badly Obama has done. Again, we all are aware of the conservative critiques of Obama. When a liberal can also offer so many similarly scathing critiques, something is definitely wrong. Anyone interested in getting a fuller picture of just what was wrong with Obama's presidency from even a liberal perspective should take the time to listen.