tl;dr ahead
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If it isn't due to the weakness of the candidate, then the Democratic party must surely be doing something wrong which they were doing right at one point.
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It would not be too much of a stretch to say that what Democrats had been doing right was simply not being Republicans. In 2006 and 2008, Democratic wins came at the expense of a Republican Party that had exhausted and discredited itself in the eyes of much of the electorate. On top of fixing everything that Bush had done wrong, Obama (like Bush before him) had promised to change the tone in Washington, and be a new kind of politician.
They set lofty goals for themselves, and then failed to deliver on them.
The health bill that had been working its way through Congress, in many ways, is an example of all the ways that Obama's promise had failed to materialize. Republicans had soured their brand by, among other things, by spending as much as they did; the health care bill was going to cost close to a trillion dollars (on top of the trillion dollars that had already been spent on bailouts). It was stuff like this that prompted the much-derided "tea party" movement's rise to power.
Obama had pledged to be post-partisan and seek bipartisan solutions. Whether any Republicans could be brought on board is questionable, but the Democrats didn't try to add anything that they could be comfortable voting for. So they just stopped trying to bring Republicans on board. And after Senator Specter switched parties and the Minnesota recount ended and made Al Franken the 60th senator in the Democratic caucus, they no longer needed to worry about Republican votes. Those 60 and their control of the House meant that they had complete control of Congress. For all the good it did them. This made the bill an entirely Democratic undertaking; Republicans had no reason not to tear into it.
This led to another problem. The Democrats could pass whatever they wanted if they stuck together, but as a result of throwing the bums out in 2006 and 2008, the Democrats had a number of seats up for re-election in areas that were nominally Republican territory. To be re-elected, they couldn't be seen supporting a bill that contained items that their voters hated, and to get their votes the Democratic leadership had to jettison the things that people in Massachusetts would be more amenable to.
On top of
that, in the Senate, to keep the moderate Democrats in line without any Republican votes to make up for them, the leadership had to effectively buy their votes. The famous example being to get number 60 for the Christmas Eve vote, Senator Ben Nelson of Nebraska traded his vote for the federal government picking up the tab for the Medicare and/or Medicaid increases the bill was going to cost Nebraska. This kind of thing was the politics as usual that the Democrats had run successfully against in '06 and '08, but even more so.
I'm leaving out a bunch of stuff here (like buying off the pharmaceutical and insurance companies to gain their support), but in the end, the result was, as some guy describing it wrote, like watching sausage be made in Upton Sinclair's
The Jungle. As the process dragged on, the bill became increasingly less popular, to the point where the majority of the public now opposed it.
And most damningly of all, the Democrats didn't seem to care. It's understandable, since a national health care program has been their dream since Truman was president, and they were closer than ever. But the electorate doesn't like to be ignored.
And then came the special election in Massachusetts.
If I've been talking a lot about the health care bill before getting here, this has been the leading political issue of the past six months, and had ties to Massachusetts, too. Before the 2004 presidential election, when the Democrats were giddy at the prospect of unseating George W. Bush, someone pointed out to the Massachusetts Democratic Party that the governor was a Republican, Mitt Romney, who would appoint a Republican to would-be President John Kerry's seat. So, in a blatant partisan power-grab, the Massachusetts legislature stripped the governor of the power to appoint senators to vacant seats over Romney's veto.
This would have been all well and good had Ted Kennedy not died and reduced the Democratic caucus back to 59. To get that 60th vote, the legislature changed the law again and allowed the governor (now Democrat Deval Patrick) to appoint an interim senator before the special election that the 2004 law mandated. This just plays into the "even worse politics than usual line".
In the special election itself, having won the Democratic primary and been up by 30 points, Martha Coakley (like everyone else) took the seat for granted. Even as popular support for the bill waned, she still had a commanding lead. That seemed to change around Christmas Eve, when the Senate passed its version and Coakley was off vacationing in the Caribbean. The lead shrunk to around 10 points, and Republicans saw an opportunity and seized it. Brown amplified his pledged to be the "41st vote" against the bill, which suddenly was vulnerable from a direction nobody anticipated. This, in additon to those famous missteps of Coakley's, weakened her to the point where she could do the impossible and lose the seat, which forced Obama to personally step in to try to save her. Even then, he had to know how unpopular the health care bill had become, since at the rally he spoke at, he talked more about Scott Brown's pickup truck than that. This reinforced Brown's message of running against "the machine" and we all see where that went.
This doesn't absolve Coakley, since even with the bill being as unpopular as it had become, Massachusetts should have still elected her, given Democratic strength there. But she did everything she could to screw it up. In and of itself, saying Curt Schilling was a Yankees fan was merely stupid; saying that in Massachusetts suggested a great disconnect between her and the people she wanted to represent, especially when she tried a few seconds earlier to invoke the Yankees-Red Sox rivalry to her advantage when talking about Rudy Giuliani campaigning for Brown. (For the non-Americans who don't know, the Yankees-Red Sox rivalry is Very Serious Business.) Then she went negative in the stupidest ways possible, doing things like using a picture of the World Trade Center to represent the "Wall Street greed" Brown stood in favor, misrepresenting Brown's position on a bill to the point of slander, and, to top it all off, misspelled Massachusetts in one of them.
To wrap this long dissertation up, yes, Martha Coakley was a horrible candidate. But even still, running as a Democrat in a state like Massachusetts, for a seat that, for one brief interruption in the early 60s, was held by a Kennedy, running against the Republican Party, whose brand is still damaged as a result of the Bush presidency, in a state that hasn't really been amenable to them in a long time, she still should have won. But she didn't.
P.S.
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Is it possible that personal factors rather than the Democratic agenda were the reason behind Kennedy's repeated re-election, and that events since his death have simply exposed the fact?
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I shouldn't ignore this, because it is relevant. A great deal of Kennedy success was due to charisma. It didn't matter if the Kennedy in question was John, Bobby or Ted; they were all very charismatic. In Ted's case, this let him be both a successful campaigner (the only races he lost were in the 1980 Democratic presidential primaries) and legislator. Kennedy also didn't make the mistake Coakley did and take his seat for granted, even if he only had to seriously contest it was in 1994, when Mitt Romney came close to adding him to the scalps the Republicans collected that year.
Yes, he was loved by the Massachusetts electorate, but if they seriously disagreed with his, he wouldn't have held the seat for close to half a century, regardless of personal charisma or the Kennedy name.