Nordwell is suggesting that his discovery of Italy is like Columbus's "discovery" of America in at least one important way: both Nordwell and Columbus claimed a country which had already been inhabited by its own people for centuries. Thus Nordwell insists that he has as much "right" to claim Italy as Columbus had to claim America. But, of course, Nordwell has no right at all to claim Italy. Therefore Columbus had no right at all to claim America.
Nordwell has no right to claim Italy for another people, let alone "by right of discovery" (since Italy has been inhabited by its own people for centuries). Columbus's claim to America "by right of discovery" is like Nordwell's claim to Italy (America too had been inhabited by its own people for centuries). Therefore Columbus had no right to claim America for another people, let alone "by right of discovery."
How do we evaluate arguments by analogy?
The first premise of an argument by analogy makes a claim about the
example used as analogy. A primary rule of argumentation is to make sure that
the major premise is true. Is it true that Nordwell has no right to claim
Italy for the Chippewa Indians? (Yes.) The second premise in arguments
by analogy claims that the example in the first premise is like the
example about which the argument draws a conclusion. Evaluating this
premise is harder, and needs a rule of its own.
Analogy requires a relevantly similar example. However analogies do not require that the example used be just like the example in the conclusion. Analogies require only relevant similarities. Twentieth-century Italy is not just like fifteenth-century America. Italy is known to every twentieth-century schoolchild, for instance, whereas in the fifteenth century America was unknown to much of the world. Nordwell is not an explorer, and a commercial jet is not the Santa Maria. Nordwell suggests, however that those differences are not relevant to the analogy. Nordwell simply means to remind us that it is senseless to claim a country that is already inhabited by its own people. Whether that land is known to the world's schoolchildren, or how the "discoverer" arrived there, is not important. The more appropriate reaction might be to try to establish a diplomatic relations, as we would try to do today if somehow the land and people of Italy had just been discovered.
That's Nordwell's point, and taken in that way his analogy makes a good argument.