I once offered to help work on some docs to make them a bit more user-friendly because at the time they were quite obtuse. Theo responded with something along the lines of requesting I please go away, as this project doesn't need people like me, and then a liberal sprinkling of lots of rude names and insults suggesting I was from under a rock/an idiot/etc.
I offered help and enthusiasm for the project. He called me a lot of names and suggested OpenBSD wasn't for people who weren't like him.
That's just me. Fine, I'm a big guy, I can take it. But I then watched for months as he did the same to countless other individuals. Newb: "Hey, we could do 'X'" Theo: "No, go away, I hate you", is pretty much the tone.
Then there is the more public stuff. The stuff that is historic but a little larger.
He created OpenBSD because the NetBSD core ousted him for his attitude and demeanour towards other developers.
There is a whole section of his Wikipedia page dedicated to his "Outspokenness" which is a polite way of calling what is actually his "Obnoxiousness":
http://en.wikipedia.org/wiki/Theo_de_Raadt#Outspokenness
Nobody doubts he can write code, and that OpenBSD - and OpenSSH in particular - was a bonus to the open source World, but my point is that he and his inner circle are hostile to the rest of the community who aren't quite like them. It's a clique.
And cliques can't ask outsiders for help once they're established: they made up the rules, and they will live (and die), by those rules.
Theo had a choice: compromise, and be nice to people and understand other people's needs; or, don't compromise and be a bit of a jerk and piss people off but stay true to your own values.
He chose the latter. Fine. He should not be surprised that they are not running to their wallets when he needs $20k for electricity bills to continue running the project in that same way.
I'm not being rude about this, I'm being pragmatic. I don't particularly want to see OpenBSD die, but I can't see many people rushing to save it, and that's because the top hierarchy are perceived as - and are documented as regularly behaving as - complete jerks.
If Theo had been a little more temperate to more people, it's quite likely his $20k (and then some) would have been raised in under an hour. I know some FreeBSD guys have raised similar/larger amounts for smaller projects in the past within a day or two. How? By being nice people that other people want to support.