Every Democratic campaign I've been old enough to understand could always be summed up with one sentence: "Vote for us or else the Republican will do evil things". A completely negative message, nothing about why I SHOULD vote for them, just about why I should vote against the Republican.
There's one exception. Obama 2008. This campaign was all about all the good things he was going to do, all the positive change that was going to happen. The word "Change" was so associated with his campaign, it was a meme for years. And Obama won by an absolute landslide.
Now, of course, Obama's actual presidency, he didn't do ANY of that, and instead, was just another war criminal, like every other president. But I do believe a big reason why libs deify him so much is his 2008 campaign, and I think that carried him to victory in 2012 as well. (Even though in 2012, they DID do a bit of that "vote for the Democrat or the Republican will do bad things, and if I was able to see that after they did that with Trump, but applied to fucking Mitt Romney, I would've laughed my ass off).
Now, after Obama was so successful with "change", and the good stuff? We had the complete opposite. Nothing will fundamentally change.
Democrats really hate learning, not just from their mistakes, but from the stuff they did correctly.
Obama teetered close to the edge of having enough popular support to push major reforms that could have shaken up the whole country because everyone and their dog wanted the real estate bankers thrown in jail. Lock them up, as it were.
Instead we got what we got because they got scared that campaigning on change lead people to expect change might happen. And this time it had the possibility of being more than empty sloganeering: there was genuine popular support that could have carried some of the more serious reforms being offered on campaign. Quite a dangerous thing for the party that pretends to be a steward of status quo, bipartisan consensus, and pragmatic clear mindedness. Obama's charisma lessened the weight of the wet blanket they threw on top of the reform movement.
After him they tried to capitalize on Obamas success to continue the pivot back to safer neoliberal waters. Luckily for them the Republicans had become openly racist because a black man was president and Dems figured it was a safe move. Unfortunately that wasn't enough because then Trump showed up and offered what Obama had: the promise of changing things, pretending to recognize a broken system and offering not just to fix it but to bring reforms to it. Drain the swamp, lock her up, etc.
Trump proceeded to be such a colossal fuckup that they could campaign on "going back to normal" with success. Back to the broken neoliberal capitalism of yesteryear was better than whatever shitshow Trump had done: millions of people were fucking dead, for chrissakes! Anything is better than that!
However they got complacent again. They don't want change. They don't want people to expect change. They want people satisfied with a status quo that erodes little by little in ways the common people can still recognize. But instead of a charismatic orator they had a doddering mummy. People saw that he was, even without dementia, clearly old as fuck. And all they could do was co-opt progressive language to scold those who noticed. Don't do an ableism, Jack! It's just a stutter!
In short they only want to win on their terms. If the electorate refuses those terms? They're quite happy to lose again. After all, the Republican jackals will soon enough remind us stupid proles that we should have accepted their mediocrity. Shame on us, right?
Between his mandate, the financial crisis, and the level of class anger, he could have governed like a pink tide president or an FDR. Obviously that's not who he was. There was a huge opportunity but no desire to act, quite the opposite.
FDR only enacted progressive reforms, because the alternative was a socialist revolution.
Yes, and Obama could have similarly enacted progressive reforms in service of the larger goal of rationalizing, stabilizing, and reinvigorating a system that was showing serious systemic flaws and signs of decline and decay. And like FDR he had the opportunity to do this in spite of opposition from Congress and the courts, to seize the historical moment and plow through these obstacles. But instead he did the bare minimum and kept the status quo intact at all costs. Because failing systems can only produce failed leaders.
In 1930s most Western capitalists felt that if they don't do something, they would very soon meet Nicholas II in person, so they were mostly willing to do reforms. Now they are convinced that their dominance is unshakeable, so they don't have any reasons to do anything.
They did fear that, but I think in the US in the 30s there was no real consensus among capitalists about the nature of the crisis or what do do about it. Some of them were in denial, many turned to fascism, some tried a coup against FDR. FDR broke through this impasse, chose a direction, and acted, overcoming the opposition within his class. And it was a successful strategy for the capitalists.
In 2008, there was some elite concern and uncertainty due to several structural problems converging, but the ruling class consensus was to make some marginal changes but preserve the status quo as much as possible. Like you indicated, they were not sufficiently concerned to do more than that. And Obama embodied this outlook and implemented this strategy. And it has been a failure for their class and their system.
Edit: I guess my point is, the opportunity existed to force through a variety of possible changes and new directions, but Obama personified how the ruling class did not have the clarity or the will to do anything substantial. And as a working class we were only a nuisance at the margins. There was (objectively) an opportunity for us as well, but we had no organization, no leadership, no strategic clarity, no capacity to act in any meaningful way.