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He has never had the support of many old "New Deal" Democrats. Even is his first senate run, he was considered to be far to likely to always give the pass to big business at the expense of protection (eg even reasonable regulation) of workers, investors, etc. Count me in this category - I had just left living/working on and around the hill, and that race was the only senate race in 20 years where I favored the republican (Weicker) over the democrat, as he was the more liberal candidate. Thus, part of the traditional democratic base has never been enamoured with Lieberman and hasn't gotten behind the campaign.
Also he suffers from either arrogance or self-righteousness (haven't figured out which it is.) Go back to his criticisms of the Gore campaign - where he faulted Gore's populism as the reason the ticket failed. This grew louder as Gore started to make a comeback, beginning with the Florida Democratic Party convention in the summer of 2002. The problem is that he seemed to be giving an over-weighted reliance to some of the more entrenched democratic strategists in DC who favor a more corporate approach to campaigning, without recognizing that some of the campaign realities have changed with Bush2. This seems to have been transfered to the current field of candidates, which Lieberman (or his strategists) dismissed in terms of their campaigning while seeming to ride on Lieberman's big number advantage as being more 'proof' of their strategies rather than a recognition that he had a built in edge of name recognition. Thus they did not do any aggressive early campaign building. His pulling out of Iowa is a big indicator that their efforts - which appeared on the surface to be mostly sitting on the laurels - had failed. He who had so roundly critiqued Gore's campaigning (too populist), had squandered a natural lead.
Overall whininess. Lieberman has a tendency, when speaking, to preach in a tone that is almost whiney. This, I agree, is a more superficial critique, but it is both about some of the content as well as the tone of his speech.
Finally a distrust of how firmly he would fight off the rightwing agenda. It isn't clear that he buys into the right wing, but he does seem to fail to understand the purpose behind much of their agenda. For example, his support of vouchers - which garnered him a great deal of criticism as he was perceived to have flipped from pro-voucher before joining the ticket with Gore to anti-voucher in order to run with Gore. While his reasons may be 'upstanding' - he seems to fail to understand that the agenda behind many of those funding and pushing hard for voucher solutions stem from areas that have resegregated schools via private schools in urban districts (look at St. Louis for a prime example.) Thus this former civil rights worker, seems to blindly support issues from the right that often have at their heart an agenda which sets back that very movement to which he previously devoted energy. If he were faced with a tough Republican congress... could he really stave off their onslaughts - especially if they package the efforts in ways that appeal to his more religiously centered self in order to hide their more insidious effects? I don't know that he could.
All of these doubts, and areas that make him less appealing to base dem voters might not translate to the general public - but some of them might also impact independent voters as well. None of these are related to the more recent issues related to the war in Iraq.
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