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I chose the time period because I believe mid -winter weather would make it impractical to do this.

I can envision it happening two ways. The luftwaffe sends out a half dozen or so of its Condors from Brest, they carry extra fuel, a small bomb load, and drop their ordinance on St. John, Nfld, and back home they go. I'm not sure if even this is doable, given the distance involved, but with some adjustments or improvements, the Germans should be able to pull it off. There is the question, however, of how damaging to the morale of the average American [or even Canadian] a one time minor bombing raid on a glorified fishing village would be. And I am not trying to take a swipe at St John, but that's how the average Joe would see the place.

Or, they could go for gold, do like the Americans did with Japan in April of '42; make it a one way trip and bomb New York. Now that would be a blow to American and Allied morale, even if everyone knew that it probably wouldn't be repeated. The crews could do their deed, fly offshore a couple hundred miles, then bail out and be picked up by a U Boat at a pre arranged rendezvous point. Some might be lost in this manner, but even Dolittle lost 20% of his men.
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