In 2008 Webb County witnessed one of the most contested sheriff's races in its history when incumbent Rick Flores was defeated by former DPS supervisor, Martin Cuellar. The contest went to the courts and featured a classic, border-style showdown where allegations of illegal voting and cronyism abounded. Flores, a fiery 10-gallon hat donning figure, was well-known for going on national television and accusing the federal government of ignoring the border. Cuellar, the younger brother of US Rep. Henry Cuellar, triumphed with a margin that was fewer than 1 percent of the vote total. Now, after a brief stint as a police chief in a small Arizona border town Flores is back as an independent.

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