William Walker, Conqueror of Nations

For any of you who are unfamiliar with this colorful character, I'll sum him up for you:
He was a racist white American who wanted to see the Anglo-Saxons rule the entire continent. When he saw that it wasn't likely that the American government was going to try to annex any more of Central America for the forseeable future, he decided to take matters into his own hands. After an unsuccessful attempt at creating his own nation in northern Mexico, he made a much more successful attempt in Nicaragua, actually taking the country for a while and declaring himself president. But his army got racked with illness and, fearing that his position was weakening, fled to New York City. He tried a third time, this attempt in Honduras, but he was killed shortly after arriving. For more info, I've got a wikipedia link:
http://en.wikipedia.org/wiki/William_Walker_(soldier)
My question is, when is the best POD for him acheiving his goal of building an empire in central America and having it annexed by the US? Would he have rebelled with the Confederacy? What would happen?
 
well , having read a little about this fascinating man , I can see two periods when his dream of a central american empire may have come to fruition. THe first was his invasion of Mexico in 1854. If hed stuck to the Baja , or had recieved more support from california , he might have succeeded in creating a puppet republic , but it seems very unlikely.

no , it seems that his stint as the de-facto dictator of Nicaragua was the peak of his power. If he hadnt incured the wrath of vanderbilt with that foolish scandal then he might have survived as a indipendent state , though I suspect that he would have kept his empire to himself rather than seek its annexation.
 
Walker was a Filibuster.

Filibusters were “…soldiers of fortune who engaged in fitting out expeditions to and conducting unauthorized warfare against countries with which the United States was at peace—usually with the aim of enriching themselves
He had been invited to Nicaragua by the Liberal Party who were feuding with the Legitimist (aristocratic) party. In time and winning battles he proclaimed himself Chief Commander and then President of Nicaragua. At this point the political parties stop fighting. While President of Nicaragua Walker legalized slavery. Seems his ultimate goal was in time to take over Central America.

Costa Rica was responsible for stopping him at the battle of Rivas in Nicaragua. Then he ran into "militant opposition" from Honduras, Guatemala, and from within Nicaragua.

He left Central America for the US but came back three years later where:
He was quickly captured, this time it was by the British, who turned him over to the authorities of Honduras. The Hondurans quickly executed him.
Walker might have been able to take the Mexican Peninsula of Baja California but there was nothing much there. Its mostly an hostile desert.
Desert-sonora285-wnpa_3.jpg
 
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