I think we're all pretty sure that when it came to badass quotes about freedom, Jefferson is the all time champion. I mean, the guy wrote the Declaration of Independence for heaven's sake. That automatically gets him into the final four of freedom right there.
This particular shirt is based from his quote "I prefer dangerous freedom over peaceful slavery." Technically, T.J. was waxing eloquent with his boy Madison when he wrote it in 1787, going with the stuffy Latin version Malo periculosam, libertatem quam quietam servitutem.
The fact that he swapped in the Latin with buddies likely meant it was a pretty common rejoinder for the Founding Fathers crowd. "Yo T.J., dangerous freedoms my brotha. Dangerous freedoms."