$5000 to just enter not guilty and likely pay an attorney to defend it / accept dismissal may seem realistic. Thing is, that doesn't leave much payout to defendant. And a fair number of those pleas will be going to trial. That entails conviction risk, and regardless of time dealt, that risk will carry a higher price.
It could be arranged as a charitable contribution ('to encourage employment of the jury system',) and thus be tax-deductible.
Nonprofits, NGO's and crowdfunding appear to be a hot ticket these days. Set one up, pick some jurisdiction somewhere, camp out on the courthouse steps with your cash and attorneys in hand and see what works. Also, no figures were presented regarding cost per case in court system. That matters too. You might be initially faster to jam it, but don't be too sure they won't deputize and set up courts on the front lawn in response. You might have better success paying that $5k to vote however you want them to for the next decade (say defunding things) after their case/time as it might currently go is up. Or as someone said, run nullification TV ads and mailing campaigns. Etc. Not sure what this has to do with cypherpunks, unless you count anonymous bitcoin donations from these CEO's, etc to your project. Last, Joe crack dealer isn't newsworthy or profitable and will be let go to make a docket slot for Joe CEO. So you might have trouble getting funded from that sector without some rethink.