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RE: What if...Benjamin "The First American" Fanklin Fought Theodore "Teddy" Roosevelt?
Fun post, my friends and I have come up with similar 'epic battles' between historical figures.
One of my favorites is who would win in a battle between Andrew Jackson and Abraham Lincoln. Lincoln has the height and reach, and the experience of a log splitter. Jackson is known for being an unmitigated bad ass and mean as hell, 'Old Hickory'.
We haven't done the depth of research into it like you have in this post, but it's still fun.
If you can't tell, I think the safe money is on the side of Jackson, as long as he can avoid Lincoln's axe hand, move in close, and send him packing all the way to the next life, just like he did with the bloody British.