Is there any practical difference between transferring ownership of the trademark to Automattic vs. granting them an exclusive license that they're able to sublicense?
It makes sure even if Automattic is no longer in good hands, the Foundation can protect the WordPress brand from Automattic.
(I work at Automattic but did not specifically checked the details of the trademark agreement)
https://tsdr.uspto.gov/caseviewer/assignments?caseId=7882673...