This argument — could President Obama have gotten progressive bills through? — is ultimately unknowable because he didn’t try. That’s the problem.
On his 3 big bills — the stimulus, health care, and financial reform — he failed to push what the country wanted and needed.
On the stimulus, he shot for a relatively small figure, partly because of a concern about deficits.
On health care, he dealt away the public option — the single thing that might have challenged the corporate stranglehold on health care.
On Wall Street reform, he killed the effort to break up the banks and opposed the tough measure on derivatives.
On the first one, I think it’s very plausible that Obama left some stimulus money on the table with a low opening bid. I think this was a more difficult problem than some do — there was almost certainly a point at which primary-fearing Republicans would have bailed on the whole thing — but I think he probably got less than he should. But it also seems pretty obvious to me that whether Obama had a successful first term or not doesn’t hinge on whether the stimulus was $770 million or $870 million. So let’s move on to the real key, the ACA.
Here, the most obvious problem with the argument is that conservative Democrats who were both ideologically hostile and had good interest-based reasons to oppose a public option held all of the cards. Nobody has explained what leverage Obama had to make the Nelsons and Liebermans support a public option, or explained how Obama forcefully advocating a public option somehow would have moved them to support it. Arguments that the optimal strategy would be been for Obama to forcefully advocate single payer make even less sense; empty threats don’t provide leverage, and associating health care reform with socialized medicine is about as bad a strategy for attracting support from red-state Democrats as can be imagined. Maximalism has real risks — especially when there are no votes to spare — and because there’s no reason to believe that the votes were there for the public option under any circumstances the approach is basically all downside.
And it’s also worth noting that it’s not as if we don’t have examples of a president trying exactly this negotiating strategy. At the time in his presidency where he had a political environment most similar to Obama’s first two years — immediately after his re-election — Bush engaged in precisely the same kind of tactics that we are assured would work brilliantly if only Obama used them. He took a maxmimalist position on Social Security, took to the bully pulpit for a year of messaging, and got…nothing. And as we know all too well, he didn’t fail because there aren’t any Democrats who are sympathetic to changing Social Security for the worse. Rather, by making it clear that his desired goal was destroying Social Security, he made compromise politically impossible, allowing the Democratic leadership in the House to keep the Blue Dogs in line. (And as for the Overtron Window, that was already moved in the 90s anyway — Obama is still to Clinton’s left — but that didn’t help Bush.) The end result of Bush forcefully pushing for maximalist conservative legislation is that he had the most favorable Republican legislative environment since the McKinley administration and ended up with almost nothing to show for it. If that’s success, I have to say I prefer Obama’s legislative failures.
On a more general level, if the ACA isn’t “progressive” legislation, than none of the New Deal counts either. The American welfare state has always advanced through incremental measures that buy off existing stakeholders. Note too that it’s not as if FDR fought loudly and publicly for a safety net that wasn’t grotesquely biased against African Americans and only gave in at the last minute; he knew perfectly well that segregationist Dems were no more likely to vote for racially egalitarian legislation than Ben Nelson or Blanche Lincoln were to take on the insurance industry, but they could certainly torpedo crucial legislation if the New Deal was strongly identified with civil rights. (And nor, for that matter, was FDR particularly progressive on civil rights anyway, but since he was almost certainly more liberal than the median votes in the Senate it doesn’t really matter much.) There are plenty of things Obama can be fairly criticized for, but to criticize him for succeeding where Truman and LBJ failed doesn’t make any sense to me. The chances of getting nothing were far higher than getting a significantly better bill. For that matter, we can consider Bill Clinton, who also pushed forcefully for a very particular version of health care reform and got bupkis. This is one area where second-guessing Obama is hard to justify.