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Jekyll is not exactly obscure though.

Seems like it's a good pre-filter. The designers who do know Jekyll are likely to be pretty good and well rounded. If they only required HTML, you might end up with a bunch of guys that think they know design because they're great in Dreamweaver.

Designers these days have to do more than picking the right font and background color. They have to consider different devices, proper i18n, and accessibility. Back in 2002, only knowing html was good enough.

Why not use a Ruby tool to generate a static page for Ruby's website?

I'm sure there's plenty of designers, who know Ruby, who would do this.