In the US?
Jail no.
Freedom of speech only means you are protected by law from legal prosecution/persecution for saying disagreeable things.
It doesn't mean you can say stuff without consequences.
The consequences of anything you say, depend on who you are, and when you say it.
The rules actually change from day to day. what is acceptable yesterday, may not be acceptable tomorrow.
This is why even professional pundits get into trouble ALL the time.
Usually, saying the wrong things often means getting fired from one's job, and becoming unemployable (for an arbitrary amount of time).
These rules are very complicated, and basically anything can offend someone.
If you are afraid of running afoul of these rules, it is best to say nothing at all.