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On drug re-importation, the problem was that had it won, it would have sunk the entire healthcare bill as it would not have gotten 60 votes. Remember that the 60 was both needed and held together with very thin threads. Kerry was a cosponsor to Dorgan's stand alone bill. This would suggest if this were done as a stand alone bill, there is no reason to think that he would not go for it. Like you, I was disappointed in this vote as he had always been for it - so I suspect it was to protect the bill itself. On the Finance committee, Kerry was one of the toughest on the drug companies.
Myself - I'm also not sure the right way to go is to allow re-importation. It would seem that a better solution would be to not allow companies to use their monopolies to charge more than they do elsewhere. What they are doing is, in effect, using US sales to recoup the bulk of their research costs. If they had to give the US the same price (or some small difference) that they offer elsewhere, it likely would bring US prices down, while slightly raising the prices elsewhere. I don't know if something like that could legally be done.
On extending the Patriot Act, Kerry with the other liberals held out for 2 filibusters - each time getting improvements. His opinion was that they had gotten as much as they were likely to get. At that point, the option was to pass the extention, which removed some of the worst things or the original Patriot Act would have been extended. It was never the case that the Patriot Act would just go away. The reason is that it included many important things - including Kerry's legislation to provide tools to fight international money laundering. This legislation was proposed by Kerry in the 1990s after he and his staff unraveled BCCI. Feingold, the only one to vote against it in 2001 said in 2001 that he agreed with 80% of the bill. Kerry, Spector, Feingold and others then cosponsored legislation that included the changes they still wanted - but it was not re-introduced in the next Congress.
On "too big to fail", I assume you mean Brown/Kauffman. Here, I don't agree that the way that this amendment shrunk the companies would have helped. In 2008, all of the 5 or 6 huge companies all bought the same toxic assets and all used their "safe bank" type assets to leverage themselves with these risky investments. Had they all been split in half - to be half as big - in maybe 2006, it is not clear that any of the parts, which would have the bankers and the derivative writers, would not have done the same thing. It is not clear at all to me that this would have limited the problem at all. So, this is something that might have done little to solve the problem, while putting the big banks at a disadvantage with their international peers.
Not all economists favored Brown/Kauffman. A real "too big to fail" action would be to reinstate a modern version of Glass/Steagall, which the Volkner rule to some degree does. (In the bill, it is not clear that this will be done - this is something worth watching when the conference report comes out.)
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