Sandro Groganz has an interesting post where he attempts to calculate the value of the MySQL brand as a component of the acquisition price Sun paid. Here's the punch line: "As of today, a whopping 85% of MySQL’s economic value added can be attributed to its strong Open Source brand." I haven't checked Sandro's math in detail, but it's clear that brand is a huge component of the value of MySQL."

Now many people will stop here and think, "That's insane. Brand is just marketing fluff like logos and skip intro graphics!". Not so fast. Marty Neumeier of Brand Gap fame says that a brand is "a gut feeling and... an approximate - yet distinct - understanding of a product or service."

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I support Marty's definition, I but tend to think in analogies. It's a weakness :-). So I always say that a brand is a conceptual bucket in the mind of your customers that you fill or empty through every interaction.

The bucket can be full or virtually empty, and the contents can be beautiful or disgusting or something in between. It depends much more on what you do than what you say.
Getting back to MySQL, their brand was in part built by the greatness of their technology, but also by their people and their community. All those keynote presentations by their executives, all those support resolutions, all those wise decisions made while interacting with their community, etc. It all combined to filled their brand bucket to the brim with good stuff. And it turns out that their brand stuff is very valuable on the marketplace.
The key question now is whether all that brand goodness is transferable to Sun. It comes down to the people. When Adobe bought Macromedia, they made a point of slotting Macromedia leaders into many, many key positions in a conscious bid to make sure that Adobe got a full infusion of "the Macromedia way" and to send a clear message to the Macromedia customers that they valued what Macromedia stood for. It worked to a very large degree. Adobe changed in many positive ways over the ensuing two years, and its revenue, market perception, and brand affinity data all moved up and to the right. Sun is saying they plan to do something similar. Let's see if they do.
So how this does all relate to Drupal? Well, we need to ask ourselves what the state of the Drupal brand is today. How full is our bucket and what's in there? Is it an inaccessible cult/niche brand that only the insiders appreciate or is it broadly recognizable even among non-users? And what are the Drupal brand drivers?
The technology is certainly a huge part of it. Getting the little things right and aligning around a few timeless themes that everyone knows makes it easier to express a brand through the technology itself. Things like tag lines and messaging and Drupal.org information architecture can all play a role, but they are mostly packaging of the brand - not the brand itself.
Let's not forget the human element. A big part of the Drupal brand is in the people in the community (who they are) and how they interact on a day to day basis - especially as it relates to outsiders/new arrivals. If there are very few experience designers in the community and those who try to join don't feel welcomed and valued, you can be quite certain that "user centered" will not be a top attribute of Drupal.
If nobody in the community seems to care about documentation and tutorials and cookbooks, you can be certain that "approachable" will not be a top attribute either. Think of how you would perceive Drupal as a newbie dropping into #drupal on IRC, in the Drupal.org forums, etc. Are people inclusive or cliquish? Are they diverse or monolithic? Are they dedicated to quality and elegance or prone to expedient compromise? Are they self-assured and generous or paranoid and begrudging? These are value choices we all make each day, and the sum of the parts make up the whole of the Drupal brand.
And of course Acquia, where I work, has it's own set of branding questions. To me, talking about what I want our brand to be is not as useful as defining our culture and values and then putting together a team who will live it every minute of every day. That's what fills the bucket with good stuff. We're just getting started, but it's feeling good so far from inside. Time will tell.