Assuming that Cleveland's second first rounder doesn't win the lottery, do you think there's any chance they'd trade the pick for Jackson?
Since they have Barron, I wonder if they'd be interested in reuniting the two along with whoever they get with their first pick to try to create a team that can win some games now rather than rebuild. Yeah, they'd be taking on salary and wouldn't necessarily be a playoff team, but they'll also be pretty desperate to get people to come to games.
What about something like this where we take on Jamison's contract? Obviously, that trade is a lot less appealing (almost an even swap of salaries owed), but we could pay Jamison $15M next season and be done with it rather than $19 for two more seasons with Jax.
Imagine something like Kemba Walker and one year of Jamison for Jackson?