Elias is the best talent evaluator in the game in my opinion who does love his "prospects" and is the opposite of Dave Dombrowski who has multiple championships. This is a new bridge for Elias to cross and I wonder if the new owner won't encourage him somewhat. He will find new talent but he night miss an opportunity being too cautious as well.
I "think" Holiday is the easiest of all his pieces to trade since Gunner is the best shortstop in the game and Westbrook has second covered already at an all star level. Ditto with Bassillo and Rutchman at catcher. Holiday and Basslio plus for Skubal as the "guts" of a deal just makes sense. My opinion.