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I can't pretend to know the subtleties of our current political climate, and what Dean's standing is within it, but: I think one of the first unwritten rules of politicking is that if you can wiggle by with ambiguity, do it.
Political tides ebb and flow.. yesterday's enemy is your pal, etc etc. Strong, opinionated politicians litter the dustbin of history. Sad fact, but there it is. It's the same reason that there's a direct correlation between the success of a politician and their relative centrism. By taking the middle path, you have more to gain from both sides of the aisle than you ever do from the extremes of one alone.
So, I think the question instead of "what did he have to lose?" instead is "what did he have to gain?"
(Note: I don't condone such machiavellian maneuvering, but that's why I'd never make a good politician.)
Dean doesn't have to do anything to win favor with lawyers at Waller. He attended law school with most of them and his wife once worked there. He's known most of those people for 25 years. They're his boys.
During the campaign, I thought the allegation (courtesy of Woods, via bitter ambulance chasers who supported Briley) was that Dean had doled out work, as law director, to Waller in exchange for support as part of some sinister master plan to run for mayor which he had been harboring for years. So now it's vice versa?
Also, calling Waller simply the "May Town lobbyists" is a vast oversimplification. Waller has plenty more interests than that, which admittedly may not be a good thing.
As to your ultimate question, I think Dean has larger things on the horizon, e.g. the takeover of the school system, which will require all of political chips he has and he may not have felt inclined to weigh in on an issue which he perceived there to be enough public opposition to take it down by itself.
At this rate Caleb, you're never going to supplant the Mayor's Office masseurs at the City Paper with the soft touch they reserve for Mayor Dean. If you ever want a cushy spot near the courthouse communications office you're going to have to stop asking critical questions and throw them the slow pitch to plant deep in the bleachers. A puff piece will write itself if the communications people don't do it for you first.
Now excuse me while I go find a way to link this post to another audience.