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Following on MinistryOfTruth’s diary on whether or not this is a matter of chess, it occurs to me that even if it were that, there would be some very serious problems with Obama trying to play that game with this Congress. (Or any Congress, but especially this one.)  The problem with eleven-dimensional chess is this: even if you can outsmart your enemies, people who are nominally on your side tend to miss your point and play against you inadvertently. Especially in DC, where as we all know, some truly dumb and mean people tend to become very, very powerful.

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I'm not saying that's necessarily what happened here, especially given Obama's track record of putting bipartisan consensus ahead of the common good even when he really doesn't have to. But when people talk about super-sophisticated strategies like we tend to credit Obama for, I am always reminded that those strategies can be very dangerous. Why? Simple: no matter how foolproof your elaborate plan is in the abstract, in reality you have to depend on everyone else involved not only being dependably on your side, but also being smart enough to understand what you're up to. It's very rare for that to be a realistic expectation.

Sad to say, I learned that lesson while working as a political organizer several years ago. I made the dumb mistake of accepting a job with a state Democratic party (I'm not going to say which one here, as I don't wish to reopen any old wounds) where my job was ostensibly to develop a grassroots campaign on behalf of the state party's political coordinator. Now, you might be thinking that's an oxymoron - a grassroots campaign is, by definition, not run by a fatcat sitting on his ass in the state capital who doesn't know or care about what people out in the field think of his plans. And you'd be right. Which is why said my taking the job was a dumb mistake.

But I had taken the job, and I was stuck with it, unless I wanted to resign. In retrospect, I should have done that as soon as I got out to the field and started talking to people about our plans. It turns out my boss was deeply unpopular with the rank-and-file party volunteers, and with good reason. During the previous election season (which had been a bad one for us), the state party had run a very top-down campaign where no one anywhere near the actual voters had any say. So now they wanted nothing to do with the party establishment. In other words, what my boss really wanted me to do was develop a new base of volunteers to replace the old one because it was collectively pissed off at him.

Still, I was young and idealistic and I really wanted to do my part. Besides, I hate being a quitter. (That has gotten me in trouble in a number of situations when I really would have been better off throwing in the towel, actually.) So I tried to mend fences. I tried being an upbeat advocate for the program, which simply involved a series of phone calls to the “best Democrats in the state” to drum up support for the next political season. (I put that in quotes because most of the names we were given turned out to be not active at all, or Republicans, or in not a few cases, dead. As you have surely surmised by now, nothing about this whole program worked the way it should have! An awful lot of the people I called hung up on me, or told me politely that they weren’t active and never had been. Some even told me I ought to stick to calling people who were more active – of course there was no nice way to tell them I thought that was what I was doing!)

However ill-managed the program was or how low the value-added was, the whole thing was simple and straightforward and intended to build support for us in the next election. I didn’t like the program, but I certainly did like end to which it was a means. That’s one reason why I refused to give up despite the extremely negative response I received from nearly every party activist I met with. In one county after another, I went into the central committee meeting with a public façade of unalloyed support, and evangelized for the program as best I could. I offered nothing but praise and encouragement, and conciliation to the local volunteers. And I ended up with virtually nothing to show for it. Most of the time, I ended up making all the calls myself, or at least as many as I had the time to make.

I saw the real problem – the bad blood between the party establishment and the grassroots – and I tried to fix it. I tried reaching out to local and county-level leaders and trying to bring them to the table with my boss for a heart-to-heart talk. Didn't work at all. Neither side would give an inch. As a result, I was in a lot of hot water with my boss for not accomplishing much of anything. After striking out in several counties, I got a new idea for the biggest county in my territory.

That county was a risky place for me to show up at all, because the committee chair there was a famously manipulative, nasty individual who had alienated a lot of good Democrats into inaction. Most of those who were still active were very much under her thumb. I had nevertheless tried reaching out to her over the phone several times, figuring if I could get her to support our program, the others would no doubt fall in line behind her. But as usual, she had only pushed back on my every request, refusing to meet me halfway on anything at all. Everything she said during our several phone conversations was clearly designed to throw me off my guard and make me uncomfortable. She even made it clear - between the lines - that she would never return my phone calls, so I had better only call her when she was home.

Now, if I'd been realistic about my chances of success, I'd have skipped the committee meeting there entirely. No point in reasoning with someone like that. But I had a brilliant idea involving a sort of reverse-psychology: go to the meeting and level with people. I know you don't like this idea, I know your hearts and minds are elsewhere, I realize it doesn't make a lot of sense to you, but please, take one for the team. Understand that if you want to lash out at the party establishment, you’re ultimately hurting no one but me. I’m just a guy right out of college who loves the Democratic party and is trying to do right by it. Sound absurd? Out of context, it would to me too. But based on the realities that were facing me at the time, it was not only a perfectly legitimate strategy, it was the only one with any real chance of success.

And here's the kicker: It worked. People were receptive to my pitch for the first time. They felt for me, they were willing to work with me and help me out. They did have a low opinion of the program, but I have no doubt that would have been the case no matter how much cheerleading I might have done. As for the county chair, she refused to have anything to do with it. She said at one point “I think it’s fair to say you dumped this in our laps, isn’t it?” (Well, no. I had tried repeatedly to get her to put the word out as only she could do, and she had refused. But I didn’t argue the point because I was in a room full of her minions.) But that didn’t matter, because I had won the support of several others in the room, and we were finally getting somewhere with the program. I walked out of the meeting that night proud of a job well done, a risky strategy that had worked perfectly.

But then came the next morning. I got a call from my boss, and he was absolutely furious. You guessed it: the evil county chair had called him and said I had been talking trash about the program and never even tried to make a case for it and, golly, of course she felt it was her duty to let him know what a lousy job I was doing. For the good of the party, you’ll understand. Now, you might be thinking my boss should have known how manipulative and untrustworthy this other individual was. He should have known, but he didn’t. Besides being a rather dim bulb, he was just too wedded to his program and unable to consider the possibility that people were not willing to get behind it on its merits. I’m quite sure that the county chair recognized this, and simply saw him as a useful idiot. I tried repeatedly to explain to him that my goal was getting the work done, nothing more or less, and this was the best possible way to do that given the circumstances I had to work with. But to no avail. He not only wouldn’t listen to me, he added insult to injury by arguing that the county in question was “the easiest f***ing county in the state! It’s got volunteers, it’s got organization, it’s got a great leader!” That was the moment when I realized he was willfully ignorant about the true situation – especially in that county – and I wasn’t ever going to be able to change that.

Of course, ultimately nothing got done. That’s bad, but it gets worse. I also had the rotten luck to be roped into working at an event with the county chair who had ratted me out. (My boss had never named names of who had called him, but I’m not stupid.) While passing by me at one point, she flashed me a sugary smile and explained that “Sometimes you have to be an advocate for things instead of saying, ‘I know you don’t want to do this’ and so forth.” I’ll never know for sure if she realized that 1) being an advocate for the program was not going to fly in this case, and 2) she was a substantial part of the reason why it wouldn’t work; but I think she probably did. That comment was just one last twist of the knife against the state party, and against me.

Now, do I think Obama has that kind of backstabbing to deal with? Probably not. He’s the president of the United States, after all, and that’s rather more powerful than a low-level field staffer. But I see the principle here as very much the same: even if he did have some brilliant grand strategy to slip a decent program by the House Republicans, he would still also have to face the “help” from Democrats like Kent Conrad who actually want to give Boehner more than he even dared ask for, and the Very Serious People in the media, and Congressional Democrats who are selfish and/or territorial about their particular interests, and others who want to do the right thing but just aren’t smart enough to see what he’s up to. (I have also worked on Capitol Hill, incidentally. There are some brilliant people among the Congressional staff, to be sure, but there are also plenty who are only there because they know someone who gave their boss a lot of money. You can guess how good they are at their jobs!)

You could, of course, argue that a truly comprehensive game of political chess will take all that into account and find a way around it. But that’s my point: anything that elaborate simply isn’t realistic. Now, what would I do if I were Obama? What I hope I would do, at least, is be blunt and tell the Republicans they lost and our policies are what the people voted for, end of story. If we go off the fiscal cliff, we only have a few days to wait until the new Congress is sworn in, with more Democrats and fewer nutjobs. The House will still be Republican, but it will also be subject to at least a few days of the PR nightmare that would come with having done nothing, and that would give us a good chance of picking up enough Republican defectors to get a decent bill through. It’s simple, it doesn’t depend on thousands of other people figuring out your grand strategy, and we have every reason to believe it would be effective.

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