AHC Hanseatic Colonization of America before 1492

How can the Hansa colonise parts of North America? I know that the Hansa was just a league of cities so how could German cities found colonies in America before 1492 in the 14th and 15th centuries during their height?
 
The problem is: The Hanse had become complacent at that time. The equivalent of corporate fat cats. No money for crazy experiments. And there were no strong German princedoms yet.
 
With difficulty. It's not hard to see how Hanseatic merchants would learn about the existence of North America. It's quite possible they knew IOTL, at least in vague terms. It's harder to see how it would be worthwhile for them to pursue a colonisation effort. In the 14th and 15th century, nobody had surplus people to get rid of. They'd just gone through the plague epidemics.

One untested idea would be a lasting conflict with Norway (which would basically mean with Denmark or Sweden, of which Sweden is the more plausible, so have Norway fall to Sweden first, I guess). With the Hansa at its height expelled from the Norway trade, they'd look for alternatives. Maybe this could happen in the context of an Anglo-Hansa naval war. Norway decides to stick it to Lubeck by only allowing English merchants to trade. I am not sure this holds water, economically, but it might work for a motive.

Hansa ships already reached Iceland. With growing demand for stockfish, Icelanders and Danes would explore fuirther fisheries, and the Hansa would follow. Seasonal encampments in southern Greenland are established, reviving the dying Greenlander settlements. The demand for stockfish still cannot be met, but the Hansa merchants, at this point holding a de fact monopoly, diversify into whaling. Whale oil and whalebone support the exanding trade and pay for the costs of a steep learning curve on arctic navigation.

With Greenland a regular summer home to whalers (something a lot like the Skanör herring boden), it is a matter of time before someone comes across the Newfoundland Banks. There is your stockfish.

The problem here is economics. I doubt that this is going to be cheaper than bringing the stuff from Bergen, so you'd have to posit the king of Norway holds his grudge forever. The same is true for furs - the initial terms of trade with the natives would be extremely good, but it will still take a political development to make them competitive over Russian furs.

I think your best bet to make this stick is to reorient the Hansa. Many Dutch cities were Hanseatic, but in the end, the Hansa defined itself in opposition to the Hollanders. If the Rhine mouth were to become as Hanseatic as the Elbe and Weser, there is your venture capital, your Atlantic orientation and your manpower pool. but that would be a cultural PODS with much greater implivcations for European history than some (necessarily small) American colonies.
 
So why did the hanse break with Holland?

I don't think they ever broke with Holland. Rather, the wars with Denmark and the focus on the Baltic and Norwegian trade routes led them to see the Rhine mouth as a market rather than as territory. The counts of Holland also saw the hansa merchants as interlopers, but that didn't need to stay that way. I think the biggest factor was that Cologne never really developed a Hanseatic identity to the extent Bremen, Lübeck or Stralsund did. If it had, the Hansa could have taken a different perspective. It was easily the biggest and richest of the Hanseatic cities, just not a very committed one.
 
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