What hurts the Mob is not the sophistication of the technology,but the naivete of the guys being recorded. Guys like Gambino,Genovese,etc,were never caught on tape regardless of the methods used.
You always assume that someone is listening. If you and one other guy are in an open field in Omaha at 3 in the morning,you still speak as little as possible,using nuances in speech and subtle gestures to get your point across.
Gotti was a good example. Even though he felt 100% safe in the Cirelli apartment,he should have still refrained from naming names and discussing specific details.