Fascinating. My discussions with WMF Trademarks and WMF Fundraising lead me to think that they didn't know of the existence of these historical arrangements, because if they had I would think that they would have swiftly approved the license request for logo use on hats, modeled after the agreement with WMFR.
My experience with WMF Trademarks in general has been mixed. Sometimes they're great and resolutions are swift, and sometimes there's clunkiness and dropped balls. The situation with logo licenses for apparel is one of the latter.
Pine