Thank you, Dean.
I think your underlying concern is that CloudBees and Jenkins are "inextricably linked" because of CB's deep involvement in the project, or to put more bluntly, a concern that some people might perceive the Jenkins project as a CloudBees project, when it isn't. That is indeed something we the project has been careful about. And on this I have two points that I want to make.
First, the test in question here is whether a CloudBees product (CloudBees Jenkins FooBarZot) would make people think that it is an authentic official "product" from the Jenkins community project. That is a confusion that goes in the other direction from your concern, which is about people thinking that Jenkins is from CloudBees. Put differently, I don't think I'm hearing from you that "AcmeCorp Jenkins FooBar" can confuse users that it is from (or the same as) the Jenkins project and not from AcmeCorp.
Second, as a creator of the project that far predates the birth of CloudBees, and as a person who has gone through the whole Hudson/Jenkins split, the well-being of the Jenkins project is very important for me. And I think CloudBees has been respecting the project's independence very much. The trademark is with SPI, the decision making process is in the project meeting and the board, and we sign the same CLA. To the best of my knowledge, we've made CloudBees live by every rule we set for everyone. If CloudBees have failed to do that, I will try to correct those. But here, I think you are saying that actually "AcmeCorp Jenkins FooBar" would have been fine if AcmeCorp is not CloudBees but something else --- say Oracle, Praqma, or some such. It's one thing to be shot down for asking a favor for being a big contributor. But this is about getting penalized for being a big contributor. That's reverse meritocracy!
In addition, if I may make an utilitarian argument, as an OSS project we should "use" commercial interests to our advantages. This isn't a zero sum game; when we make it easier for companies to contribute and get involved in the project, we the project benefit, in terms of faster growth, more features, etc. I've long held that view, and that's why our license is MIT license, not GPL. This mark usage request is really nothing more than a simple reflection of the "hey, Jenkins Enterprise by CloudBees is really mouthful" feeling (and probably a bit of desire to emphasize the "CloudBees" part, I'd imagine.) If there's a growing concern about the role CloudBees is playing in this project, I'm happy to have that conversation. But it really feels like somewhat separate from the specific question at hand here.