[...] not everything has to be blessed by Stallmann to be acceptable
Regarding this point, Stallman certainly does endorse Free Software. And so much of what is in OpenBSD is Free Software—software that respects a user's software freedom—and the same goes for OpenSSL. Stallman (and his organization, the Free Software Foundation(FSF)) are known for standing up for a user's software freedom. Non-copylefted Free Software is Free Software. Furthermore, in 2004 the FSF gave Theo de Raadt an award for the Advancement of Free Software, "[f]or recognition as founder and project leader of the OpenBSD and OpenSSH projects, Theo de Raadt's work has also led to significant contributions to other BSD distributions and GNU/Linux. Of particular note is Theo's work on OpenSSH". A free system need not include GNU software or be licensed under a GNU license (such as the GPL) to respect a user's software freedom.
The FSF is quite clear why it doesn't list OpenBSD (or the other BSD distributions) in their list of Free system distributions:
FreeBSD, NetBSD, and OpenBSD all include instructions for obtaining nonfree programs in their ports system. In addition, their kernels include nonfree firmware blobs.
Nonfree firmware programs used with Linux, the kernel, are called "blobs", and that's how we use the term. In BSD parlance, the term "blob" means something else: a nonfree driver. OpenBSD and perhaps other BSD distributions (called "projects" by BSD developers) have the policy of not including those. That is the right policy, as regards drivers; but when the developers say these distributions âoecontain no blobsâ, it causes a misunderstanding. They are not talking about firmware blobs.
No BSD distribution has policies against proprietary binary-only firmware that might be loaded even by free drivers.
Including nonfree software and pointing users to nonfree software is quite common among those who endorse the open source philosophy, as the FSF has long pointed out (older essay, newer essay). The open source movement's philosophy is a development methodology built to toss aside software freedom for practical convenience in an attempt to be "more acceptable to business". So this philosophical difference sets up a radically different reaction in the face of reliable, powerful proprietary software. Quoting the newer essay:
A pure open source enthusiast, one that is not at all influenced by the ideals of free software, will say, "I am surprised you were able to make the program work so well without using our development model, but you did. How can I get a copy?" This attitude will reward schemes that take away our freedom, leading to its loss.
The free software activist will say, "Your program is very attractive, but I value my freedom more. So I reject your program. Instead I will support a project to develop a free replacement." If we value our freedom, we can act to maintain and defend it.