For the purposes of this question, we'll confine Trump's "inner circle" to the following people:

Note #1: Links go to articles related to potential criminal charges against individuals.

Note #2: Steve Bannon is included on the list, even though he and Trump have had a falling out, simply because of how influential he was earlier in the Presidency.

Will a judge sentence at least one of these people to a jail sentence by Jan 1., 2023?

Resolution is positive even if the person is pardoned, as long as the pardon comes after conviction. We will also count jail time assigned by a judge per contempt of court, etc., if any actual time in jail is spent.