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In light of recent events, here's OpenStreetMap editors discussing naming of the Gulf of Mexico
(community.openstreetmap.org)
This is a most excellent place for technology news and articles.
Frankly I agree. From my personal experience, every single native Chicagoan has been calling that particular building "Sears Tower". Even though the name has been officially changed for more than 15 years by this point...
And I thin OSM actually handled this quite well! The original Sears Tower name is still available as an "alt_name" tag on OSM as well, I just double-checked and yep it's still searchable on the map