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Don't forget that when he started out, he was really the guy in the #4 or #5 or #6 political slot in the state- no one paid much attention to him. Ted Kennedy and Tip O'Neill were the heavyweights sent to Washington, Dukakis and the Irish crowd (Moakley, White, the Bulgers, etc) and maybe Silvio Conte were the powers in the state.
Tip and Ted were hard at work in the '80s stalling the Reagan/Bush crowd from ramming through their agenda, judges, etc. Control of the Senate depended on stodgy conservative Democrats like Sam Nunn and the rest of the aging Southern Democratic contingent who, on their seniority and due to their age, hogged the major Committee jobs (Ways and Means, Armed Forces) mostly for the pork barreling and vanity and moving jobs to their states. None of them wanted to do the hard messy work of pursuing investigations, and their reelections weren't all that safe bets, so Kerry was the man best placed (the Reagan people hated Massachusetts and vice versa) by experience as prosecutor and soft home state competition and being relatively young and with deep integrity and fight in him to do the hard work against the Reagan crowd- Senate investigations.
It was hard work and risky and not well rewarded - but Kerry and the others got Iran-Contra and S&L and BCCI far enough to endanger the Reagan and Bush principals, as intended. Watergate is always in the room in Senate investigations- but O'Neill and Mitchell and such realized that getting Reagan or Bush impeached was not the kind of political move needed in those painfully reactionary times in the electorate. Gutting the Administration hard core for Nixon aide types of violations was the strategy.
Kerry was in Kennedy's shadow (and the rest of that older generation of Senators) most of the time in the Washington game. As a Brahmin family scion he wasn't quite part of and with a certain amount of disdain (some say snobbery) stayed out of the Irish political fray in Boston, got along pretty badly with that crowd over time, really. But Dukakis was finished after the '88 election, Tip O'Neill retired, 1990-94 cleared out most of the Southern conservative Democratic Senators and Ted Kennedy lost his role legislative/Committee chair roles with the Senate majority. The three Republican governors were elected largely in order to do battle with the increasing hackery and patronage of the Irish state politicos in the state legislature, starting in 1990 with Bill Weld and probably ending now that Romney has knocked out Billy Bulger (who was actually doing a surprisingly good job fundraising for the UMass system) and Tom Finneran.
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Kerry is, in a way, a standard Brahmin, most easily compared to Bill Weld really. He's not all that interested in particular things- and not personally all that imaginative- but he'll learn all the important detail and is an excellent manager and delegator- great at picking people-, and he demands of himself to live up to what he expects of others. I think what motivates him is the belief that the Texas/Nixon-redux crowd is a corruption of, a perverse indulgence and arrogant failure to recognize, what the American upper crust historically represents in the world: a skeptical yet energetic, but patient, force for real progress. The particular issues rarely matter to him very much, as they don't to any real politician- anyone who's had dealings with him can tell you as much- but he has a pretty good instinct of which one is a relevant bottleneck or a trap in the big picture. Be it to himself, or his opposition. And he goes after fixing his own and worsening his opposition's relentlessly- Bush has fought and fought, yielded ground copiously and exploited every inherent advantage, but Kerry has been pretty efficient. The logic of removing Bush is that Bush represents a perversion of American destiny, a reign of clever idiocy, that will soon endanger the genuine substance and the earnests of American life. To be a liberal is to recognize what is significant, actually worth defending and worth creating and worth fixing, and to do it, and not to do or impose all these insightless, vain, selfserving things that the other side does - that's Kerry's liberalism. An argument about human dignity. It pisses off the ideological until they see that it matches the ends they seek, even if it is a different- sometimes slower, sometimes faster- road to them.
But people don't like to think of him that way. A strategic planner is not the way workers like to imagine their boss- as a schemer- and a man of some real wisdom is utterly beyond ken to average people, acceptable only in form of a blundering or lucky or at times insightful situational tactician. That's been exploited by the Bush team to the extent possible- with the flaw that their boy has demonstrated complete strategic failure in all he's really done in office, and his "wisdom" is a matter of 'faith'. So people take a while to 'get' John Kerry's politics and 'get' John Kerry as a political and private person, but when they do there's either a dignified agreement with the aggregate or a violence that emanates from their vanity. (Check out the various responses around here and then the Republican responses to him.)
Ted Kennedy is hanging on in office in the hope of doing a little more to make the U.S. a country where civilized people can live in peace. With Republican majorities in the Senate there isn't much overtly to show for his efforts- a few fillibusters upheld, some great work in constituent services- in recent years. He got conned and burned on the Medicare prescription drug benefit, as we all know. But 2006 should roll around with him running for office one more time- and IMHO we'll have a Democratic Congress starting in '07, and Kerry in office, and there will be a good amount he'll get done on that last lap around the track.
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