The guy is infamous for being one of the most aggressive, sarcastic and trollish OSS developers out there. He's been like that for 20+ years, he's not going to change just because they are 20 grand short.
Part of the success OpenBSD has enjoyed is in fact due to this uncompromising attitude: Theo pushed hard against security-by-obscurity, binary blobs, undocumented proprietary hardware and poor development practices. With openSSH, they pretty much set the bar for security-related programs the wotld over.
At the same time, Theo's personality routinely drives away a lot of very capable developers and users, which limited the overall popularity OpenBSD could ever reach.