Try:
git config --system core.longpaths true
This will allow it to checkout the files even with longer filepaths. The issue with this would be when you try to delete it, as Windows will not allow to delete a path longer than it’s allowed threshold. The workaround to that is to rename the folders in the local repository, so that the overall length of the path is lessened. For example, a path that is alpha/beta/gamma/universe.txt, can be limited to 1/2/3/universe.txt, so that it’s length is under the windows filesize threshold.