This would be contingent on the pick not landing in the top 4.
I could see Masai making a gamble like this. Turning Barnes and the #7 pick into a top 3 player in the world is a win for Toronto, who would instantly be a title contender. With IQ, RJ, Gradey & Ingram surrounding Giannis it might be his most talented teammates of his career.
Milwaukee cannot tank as it doesn't own its own draft for awhile and this would allow a pivot to stay relevant. Dame, Scotty and whoever they draft this year should be an acceptable reload while getting much younger. They would separately be pursuing Dame trades but wouldn't be forced to move him.
Thoughts and objections?