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The money guys reduce it to mathematics, because that's what they do.
And no, it's really not all about personalities. That plays a minor role--you assume the candidate has the personality. Campaigning can be boiled down to a science, on one level. You know that you will lose certain regions (whether precinct, district, or state) by a certain margin, based on history and pre-polling data and such. You assume you will win certain districts the same way. So that leaves certain ones in play. That's where you focus your energy and money. You try to steal the edge in those districts. If you are really crafty and feeling confident, you might try to campaign in one of your opponent's safe districts to steal a few votes, and maybe hit him on a key issue he is weak on. Then he has to waste money campaigning in a district he had the edge in, not so much to win that district, because he's already going to win it, but to minimize the damage.
There are other factors. Ballots, for instance. Say the ballot has an unusual number of Hispanics on it. You expect more Hispanics to vote. If the Hispanic candidates are all Democrats, you expect a boost from this. If they are women, you get a certain boost. If they are Republican, you may have problems--more Republican Hispanics will turn out to vote, upsetting the Demographic. Same with any demographic, or ideological bent.
Given the historical turnouts, the types of candidates on the ballots, and the races up for grabs (and other things I'm not remembering at the moment), a strategist determines what region to focus money on, what ideological bent has the best chance of winning (a ballot and race that is expected to draw mostly conservative and moderate voters does not encourage support of a progressive liberal, for instance. And vica versa.), etc.
A good analyst in a normal year can look at a ballot, look at the district, and predict the race within two or three points. If the race is expected to be eight points off, it might be worth a fight, but not likely. If it's ten points off, save your money.
That's basic strategy, and in normal times, it works well enough. There is a limit to your funding, your volunteers, and your time. There are three reasons I don't like it. One, you surrender your argument. If you don't bother to contest even in a district you can't win, no one hears your argument, and that strengthens the other side, ultimately costing you votes. Two, a good candidate can do amazing things, and you might miss that chance. Three, when times are changing, as they are now, you miss the change, and you miss opportunities. I think Hackett did well because of all three of those reasons: he had a message people weren't used to hearing, he has a great resume and personality, and people are beginning to turn against Bush. I think the DNC missed a great opportunity by playing the old rules.
No one is too trusting. They are just trained to do things a certain way, and no one wants to be the one to take a risk and fall flat. So they try the tried and true methods--which lately makes them fall flat. But if they fall flat doing what's expected, they don't get laughed at, or written off as a crackpot.
People like to see conspiracies, and imagine dark, smokey rooms where all these decisions are made, with money changing hands. That happens, but it's exagerated. Truth is, most of these decisions are made by the same type of mid-level managers who gum up all businesses in the same type of business-meeting climate that hounds all businesses. There are geniuses, but they can only work so many places at once. Mostly there are just a lot of people trying to figure out what to do, just like around here. And there are a lot of liberal/progressives in these meetings, but they, too, when the money is on the line, agree that the best strategy is what has been tried before.
That's been my observations, anyway. I imagine all districts are different to some degree. But that's how and why the decisions are made. I imagine there could be a couple of plants here and there, but more than likely, they would be spies, only. It's no harder to spot a disruptor in a meeting than it is on DU.
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