Here are some ways Obama could have won big, politically, on the warrantless wiretapping law. (Which, for those who don't know, allows the NSA to spy on anyone, any time, with no real court oversight. See http://www.aclu.org/... if you don't want to read the entire bill.)
(1) Explained, straight up, months ago, that he didn't give a damn about spying, didn't think the Fourth amendment applied to email or phone calls, and was OK with the executive branch spying on anyone any time, and that he would draw the line on something else (torture, habeas corpus, etc.). That way he wouldn't have disappointed any of us later: we would have known what we were getting. And he would have looked honest and principled, if not right.
More under the jump.
(2) Supported Feingold's and Dodd's filibuster with heart-raising orations. Then if he lost, he would still have great "I stood up for you against BIG GOVERNMENT!" and "I stand on principle!" campaign lines, and an outpouring of support. Of course, this would be my preference. He would have been on the outs with Rockefeller, but it would have been worth it.
(3) Cleverly arranged to vote against the bill and orate against it while making sure that it passed in a back room. Sneaky, but politically effective. And I'd bet some of the 28 who voted against cloture actually did that.
(4) Voted for it while announcing "I think this bill is wrong and unconstitutional, but there are issues I think are more important -- I can't tell you which ones right now, but I will in a month. I have been given certain promises if I vote for it. I think it is worth getting those promises. And those promises are good even though I'm telling you about them. This may seem crass, but politics can be dirty, and I'm not afraid to get dirty." Then, in a month, pull a spectacularly good trick on another civil liberties issue (closing Guantanamo, convicting Bush of impeachment charges, inherent contempt arrests, ending the Military Commissions Act) and announce that that was the benefit of the deal.
(5) Pulled a true miracle off by executing some procedural trick which really did postpone the bill.
(6) Arranged to have a good reason to be out of town for the vote.
(7) Somehow made sure McCain was present for the vote, so that at least he'd be on the record as being at least as bad as Obama. (McCain cleverly stayed away.)
I think Obama got the worst of all worlds, politically, by this vote. Clinton was smart enough to vote against. The old pol Schumer knew to vote against. Obama just got snookered by someone in DC. Not sure who. I hope it doesn't screw him politically too badly. I think it will kill any chance of his getting any of the libertarian-minded right-winger vote -- while McCain, by staying away from the vote, has given himself a chance to get those voters back from Ron Paul and Bob Barr.