Might work once but even the “Dreaded Pirates of the African Horn” are almost immediately trailed the moment they strike and the only reason NATO can't just take them out is the hostages they have.
But I don't think you guys are thinking big enough...
An armed merchantman might be quite effective as a surprise weapon to cripple an enemy with a quick strike of missiles. Novator makes a missile launch system for the SS-N-27 that fits four rounds in an ISO shipping container. That could do a lot of damage if it sailed in to Baltimore harbor and fires a few dozen LACMs or it got within sight of a US CSG and let fly a bunch of ASMs from point blank range. Boats like this are what we like to call stage one of a “Red Dawn” or “Debt of Honor” type scenario. Great part is you don't even need to own the boat! Just send some shipping containers overseas and wait for FEDEX to say its unloaded in the states and wham!
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