Waterloo springs first to mind, but Leipzig in 1813 destroyed a much bigger French army and led to the liberation of Germany from French rule.
Laon probably sealed Napoleon's fate in 1814.
Aspern-Essling in 1809 dimmed the aura of Napoleon's invincibility.
You could argue that Borodino in 1812 was a defeat, as Napoleon lost his last chance to defeat the Russian army-in-being. Or was Maloyaroslavyets more fatal?
Or was Napoleon's worst defeat suffered on a battlefield where he was not even present? In that case, a number of Iberian battlefields might qualify, e.g. Bailen, or Fuentes de Onoro.
Laon probably sealed Napoleon's fate in 1814.
Aspern-Essling in 1809 dimmed the aura of Napoleon's invincibility.
You could argue that Borodino in 1812 was a defeat, as Napoleon lost his last chance to defeat the Russian army-in-being. Or was Maloyaroslavyets more fatal?
Or was Napoleon's worst defeat suffered on a battlefield where he was not even present? In that case, a number of Iberian battlefields might qualify, e.g. Bailen, or Fuentes de Onoro.
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