It never hurts to try. If you really want to be a political theorist, then spending a few hundred dollars on application fees is not some giant loss. It sounds like you have a really strong connection with your political theory professor, and this can go a long way (particularly if he's relatively well connected). A good letter from him that explains your low GPA, talks convincingly about your strengths, and assures committees about your potential could be a game changer.
The low quant GRE issue is harder to finesse than the GPA one. If you think that studying and retaking could bump that up, then it's imperative that you do so. Many faculty use the math GRE score as a hard cutoff and won't read any further on a file with a score in the 27th percentile. If that's the really the best score you can achieve, then you may find that you have limited options, but if you're hitting the 96th percentile on verbal, then it sounds like you have the intellectual horsepower to take on the math section if you buckle down and study.
Finally, many applicants with a low GPA go into a masters degree program, where they can excel, get good grades, and prove they're up to the challenge. You should consider this option.