I don't think a democratic mass politics is possible via Machiavellian means, I don't think the left makes sense without that sort of thing in mind, and I don't find it difficult at all to imagine a not-too-distant future where (eg) Charles and Yoshie's happiness might be more threatened by the wages of the very sort of ambivalence towards free speech they exhibit than by racial ascriptions.
Whilst I don't for a minute disregard the contribution made to the progress we have seen in matters racial/gender by structural developments within capitalism, I think great speakers, speaking freely, played the decisive role. They prevailed (to a meaningful degree, anyway) in a sea of racist and sexist discourse, not only because the time was right, but because THEY were right. And, whilst we should be wary of Habermas's sanguine belief in the power of the better argument, we should not forget that those with the better argument do stand to lose most if we start messing with free speech - especially in a time where the forces of production have afforded western lefties new and far-reaching fora.
Cheers, Rob.