who gets to fleece the AI team
I think you would need to prohibit trades to AI controlled teams. Not for the players teams would receive but after the bleeding was complete the AI would have a depleted roster. This would lead to easy wins for teams in the same division and the AI would receive the 1st overall pick every year. The race would be on to see who can trade a 1st + 2nd to the AI for its first round pick.
I could be wrong and maybe the GM brain will do the fleecing.