I wrote previously about how the Finder in 10.x up was screwy in the way it dealt with long file names.
Looks like Apple almost heard me, as they fixed that bug, but only half way.
Here is how they used to deal with it, which was pretty piss poor:

And here is how it is dealt with in 10.5 Leopard:
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I would like to say, nice effort. They truncate the file name in the center of the long file name, which is more than most would have done. Most would have chopped right off the end and just put in a “…”. Apple did the nice thing here, by giving you context to the file from the beginning and the end.
They just somehow forgot that there can be more than one level to a menu item. Why this is not built into every API Apple pushes out, so a developer need not even think about it, no idea, but it should be.
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