Mike Konczal says two of his biggest disappointments of 2009-10 have been Congress's failure to enact a carbon policy and Obama's continuation (and in some cases, expansion) of Bush-era civil liberties policies. No argument there. But his other big disappointment is that he thinks Obama never learned to lose well:
By losing well, I mean losing in a way that builds a coalition, demonstrates to your allies that you are serious, takes a pound of flesh from your opponents and leaves them with the blame, and convinces those on the fence that it is an important issue for which you have the answers. Lose for the long run; lose in a way that leaves liberal institutions and infrastructure stronger, able to be deployed again at a later date.
[Example: ramping up deportation of illegal immigrants and then failing to get Republican support for the DREAM Act anyway.]
This is losing poorly. It makes major concessions without getting anything in return, conceding both pieces of flesh and the larger narrative to the other side....This is true of many issues, ranging from unions fighting for the ability to unionize easier to the technology groups fighting for Net Neutrality. Why should these groups be happier with the past two years, even if they thought on day one that they wouldn’t win anything? How are either stronger for the next battle?
This has indeed been a mystery. It's never been clear whether Obama makes these pre-emptive concessions because he genuinely believes they're good policy or because he genuinely thinks it will draw out Republican support down the road. Neither really seems to make sense. Even if he thinks they're good policy, it's still smarter to hold them back as bargaining chips for broader policy victories. And quite plainly they did nothing to endear him to Republicans, who are almost unanimously convinced that he spent the last two years ramming an ultra-liberal policy agenda down their throats using a combination of bald lies and Chicago-style thuggery. It's hard to believe that Obama ever thought they'd react differently.
In any case, I find this aspect of Obama's presidency perplexing too. Compromise is one thing: it's baked into the cake of mainstream American politics. But I expected that even as he inevitably compromised, Obama, with his famously long view of things, would steadily try to push the public in a more liberal direction. As Mike says, this may mean eventually compromising on a policy that appeals to the broad middle of the country, but doing it in a way that hurts your opponents and energizes your friends for battles to come. Obama seems to have done exactly the opposite. It's hard to understand.