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I grew up in Miami, so I remember Jeb Bush's political runs for Governor in 1994 and 1998. In 1994, there were bumper stickers plastered all over cars in Miami that simply said 'Jeb!', but he ended up losing a very narrow race to a popular good old boy Democrat, Lawton Chiles. That was a good year for Republicans, and it was shocking that Bush got knocked by a relatively unaccomplished incumbent in a change year tilting towards conservativism nationally. In 1998, Jeb won the election against a weak opponent, Buddy McKay, and triumphed in 2002 again against a relatively weak opponent, Bill McBride. Both times he was perceived as a moderate and highly competent Governor in a relatively apathetic state, and he's always able to shield his conservative views from public view because he's in a state level position.
This track record has been compounded by the weirdness of Florida, which is Alabama in the north of the state, Cuba and New York in the south of the state, and the exurbs in the I-4 corridor in the Disney middle. Jeb's conservative politics play well in the north of the state, and have been pretty irrelevant elsewhere. Should he run for Senate, Jeb Bush will have an entirely different experience. If his opponent is Alex Sink, my guess is that he's going to have a really tough time. Sink is a wonderful and highly respected former banker who is now the state's chief financial officer. She's a very very strong opponent, and Bush's background as a semi-corrupt businessman who participated in a scheme to, get this, sell water pumps in Nigeria, will emerge.
Remember, the Bush family is immensely corrupt, but that doesn't emerge unless there's actual scrutiny. Jeb has never been subjected to any such scrutiny, but it's hard to imagine that this situation can continue if he gets a serious contender. The Bush family is in disgrace, and I don't see how that changes in just two years, especially with the rumors flying around about Jeb's personal behavior and business shenanigans.
2010 will probably not be a good year for Democrats, but just because Jeb Bush is popular now doesn't mean that he's necessarily a strong candidate in two years.
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