But why would you think like that? If, outside of any smartphone connection, someone said they'd "jailbroken" I would think "they were in jail", not "I wonder if they deserved to be there".
If you call yourself a jailbreaker you a describing yourself as an escaped criminal to many people.
If you're not a criminal, why are you in jail?
We live in an entirely nuance-free culture. We have an electoral campaign where candidates are being attacked for speaking basic French. Where an electorally significant percentage of the population believe that Saddam Hussein was responsible for 9/11 and that Barack Obama is secretly a Muslim.
When the US government is unable to successfully impart basic factual knowledge, basing a political campaign on anything with the slightest element of ambiguity or nuance is madness.
Shortly thereafter, he gets a very worried call from his brother, saying "We've been hacked!" He saw a lot of traffic in the logs from an IP connected with the word "Hacker" and got a bit panicked.