Given the height of the mountains and the width of the land mass, I would think that quite improbable. Dean will lose much of it's strength going over the relatively narrow Yucatan peninsula, which as I recall (I've visited the Mayan ruins in Tulum, near landfall) is quite flat and featureless. I'm sure it will rapidly fall apart over land on the mainland in Veracruz. That having been said, there's probably a lot more people in the area of the second landfall.. than the area just north of Belize and south of Tulum.
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Re: Dean Makes Landfall in Mexico as a Category 5 Hurricane