I learned the most by reading and writing about great speeches in high school English. Lincoln's Gettysburg Address, Marc Antony's speech in Julius Caesar, and JFK's moon speech all come to mind. Understanding why these were effective is like drilling the fundamentals in sports or music. Once you have internalized the rhetorical devices that the greats deployed, you can start to use them in your own writing.
Churchill is good too. It would be cool to see a website that takes apart great speeches and annotates their meaning and what the author was trying to get across, perhaps utilizing collaborators. Apart from the myriad of academic work which would likely just serve to confuse.
