You mean like Judge Alsup, who taught himself Java so that he could rule that Oracle's APIs are not copyrightable? Or Judge Wells, who ordered SCO to show him the code and then threw the case out when the failed to do so? We haven't done so bad on tech judges recently - it seems to me that the problem with the lavabit/NSA cases is not so much the technical side, but the classic one of government powers, and the fact that there is no explicit constitutional protections of privacy.