War of 1812—Oceanic Theater:

Which leads to America’s worst naval defeat, an unfair fight that should’ve been fairer than it was. Flouting the wisdom of Washington and the entreaties of navy-minded Founders like John Adams, Congress declined to fund a U.S. Navy adequate to its purposes—notably shielding American coasts from seaborne attack, fending off enemy blockades, and amassing diplomatic capital for U.S. policymakers and diplomats. Lawmakers chose the false economy of low naval expenditures over the insurance policy furnished by a vibrant fleet—and were taken to task by posterity for it.

A shameful tactical defeat—of frigate USS Chesapeake at the hands of HMS Leopard, in 1807—helped bring about the War of 1812. Captain James Barron surrendered to Leopard after firing a single shot when apprehended off Norfolk, Virginia—and the ensuing popular outcry helped precipitate an American embargo on British trade. So much for the battle cry of a subsequent skipper of Chesapeake, James Lawrence: don’t give up the ship! Indeed, the Chesapeake-Leopard affair could merit its own entry on this list.

As Mahan and Theodore Roosevelt contended in their histories of the conflict, the early republic erred grievously by failing to construct a battle fleet of, say, twenty 74-gun capital ships able to command America’s near seas. Though inferior in numbers to the Royal Navy in overall numbers, such a fleet could have cut ties between the British Isles and the Caribbean—imperiling British interests there, and thus perhaps deterring war altogether. Globally inferior—locally superior.

At a minimum, moreover, a muscular U.S. Navy could have precluded the sort of smothering British blockade that shut down American seagoing and coastwise trade by 1814. Forget the single-ship victories on the high seas during the war’s early going, and forget the navy’s exploits on the Great Lakes. For eminent Americans the War of 1812 constituted a woeful strategic defeat on the open sea. It was an example of what not to do in the realm of maritime strategy.

And that earns it top—or bottom, depending on how you look at it—billing on this list. The worst of the worst.