Actually the pirates feel that the FCC is restricting the Freedom of Speech Most are contrarian conformists. If they thought they would never get caught, they wouldn't lock their doors and operate in "broad daylight" Most don't do that.
Some even obtain amateur radio licensing so the FCC has something to take away. Fines are not the first whacking (generally) - its a cease and desist order in your mail box, confiscation of equipment, and for first time offenders a fairly hard slap on the wrist. When a pirate receives this letter, it's either time to move locations or stop. For those who continue the broadcast is when the FCC takes notice.
Proving, in a court of law, that it was YOU (not you, the pirate) was the offender takes more than a pass by with a yellow van. They (the FCC) has to build a case against the offending radio station. Just like any charge, they must fill in all necessary information to secure a conviction.
Some get bused quicker because of crappy transmitters that spur right up in the Aircraft Band. That will get the FCC's attention in 1 second. So will "content" such as bad or offensive language that upsets citizens. Some listeners just call the FCC to lodge a complaint of content not ever knowing they just finked on a pirate station - stating the process of investigation.
If you want to pirate FM - Use a good TX such as a Bext P10 with low pass filter. Don't cuss or be offensive, degrading the FCC, talk of reform, and how your(pirate not you specifically) freedoms are being violated will not help a pirate stay on the air longer - and listeners don't care about the FCC or freedom of speech. Generally people want to be entertained not part of a "movement".
If found personally talking like a freedom fighter only causes a drop in listener-ship.
Just play Freebird and Stairway to Heaven - instant listeners.
Or better, obtain a LPFM license.