The post has been updated to say that "The Foundation also licensed the name to the website WordPress.org, which facilitates widespread access to WordPress-related software at no charge." Websites presumably can't have trademark licenses. There must be a legal entity. Matt Mullenweg is claiming that he personally has the second license for the trademark [1], so not a website. A graphic included in the post similarly still claims that "Right to use name as part of non-profit activities" went to WordPress. With the arrow coming from the WordPress Foundation. There doesn't appear to be a non-profit.
The post states that "The right to use the WordPress marks for commercial purposes (e.g., selling software, hosting, and agency services) is owned by Automattic." The publicly available license states that Automattic has the right to use the trademark "in connection with the hosting of blogs and web sites [2]." So it looks like Automattic's rights are more limited. Maybe the license has been amended or there is an unstated belief that the license has a wider scope than the plain language of the license suggests. Having the foundation release all licenses agreements it has would help to clear things up, possibility for you, but definitely for everyone else.
In explaining how the license agreement between the foundation and Automattic happened, the post says that 'In order to effect a valid license agreement, there needs to be an actual exchange of value from both sides, which lawyers call "consideration."' But Matt Mullenweg [3] and what appears to be an Automattic employee writing for the WordPress Foundation [4] both stated at the time that Auomattic donated the trademark. Legally, a donation can't involve a consideration [5]. That would suggest there isn't a valid license agreement or there wasn't actually a donation.
We would suggest you consult with a lawyer about all that, but you are a lawyer.
[1] https://youtu.be/OUJgahHjAKU?t=442 [2] https://assignments.uspto.gov/assignments/assignment-tm-4233... [3] https://ma.tt/2010/09/wordpress-trademark/ [4] https://wordpressfoundation.org/news/2010/trademark/ [5] https://www.law.cornell.edu/wex/donation