Living in Canada allowed him to avoid the USA's onerous export restrictions on strong encryption; at a time when good, consumer-accessable encryption was expensive and patent-encumbered. The 'net is secure in no small part to his efforts and that of the rest of the OpenBSD team.

You mean DJB, Zimmerman, and others fighting the governments to change the status quo encryption policy followed by deployment of higher-quality stuff than average proprietary in FreeBSD and Linux that got widely adopted by most of the Internet? Nobody has ever showed me evidence that Theo or OpenBSD had any impact on the security of the Internet as a whole. Maybe on specific users of OpenBSD or the developers' higher-quality software. Not the big picture, though.

I'm open to specific examples if you have them of widespread changes in INFOSEC or massive adoption of better tech due to Theo de Raadt.

EDIT: I'm aware of many good apps they've made. To clarify, my comment is addressing this broad claim:

"The 'net is secure in no small part to his efforts and that of the rest of the OpenBSD team."

OpenSSH might get credit due to massive use. Good example. Past that, what else does most of the net on client side (mainly Windows & Mac) or server-side (mainly Win, FreeBSD, and Linux) depend on from OpenBSD developers?

OpenBSD led by example, being secure by default and at the expense of other considerations.

And yes, that wee piece of software that is the secure gateway of choice and has been for a great length of time; among a great many other innovations mentioned in the link in another reply.

OpenSSH?

Androids libc?

OpenBSD team made that? You got a link?

Google used bits and pieces of various BSD libcs in bionic. It's not definitive, but wiki has a list. https://en.m.wikipedia.org/wiki/Bionic_(software)

And was kicked out of the NetBSD project. This is the rest of the origin story for OpenBSD.