I will not bet in this market.

Some clarification points from the comment section:

If he is ordered to go to jail but for whatever reason does not actually go to jail (dies on the way, flees custody, etc.), this will not resolve Yes unless he is actually jailed.

There is still considerable room for interpretation of what exactly it means to be 'jailed', whether 'jailed' requires being held in a specific place or how expansive that term can be, etc.

The over-arching principle here is I would resolve yes if people say "he went to jail". If the judge says "You're not allowed to leave the state of Florida" or "You're not allowed to leave your house unless you're coming to the court", that is not "jailed". Being taken in the back of a police car is probably not being "jailed".

If the judge says "You're to be held by the X person in the Y room of this court until 5pm when I will have my decision", that very well could be "jailed" because it is being held in a place as if it was a jail. If he's sent from a court to a place known as a jail, and not allowed to leave immediately, he was probably "jailed" even if he isn't literally behind bars.