All the difference in the world.
In situation #1, I’m picturing Henry as a super involved micro-manager who doesn’t let Dombrowski go to the bathroom without prior approval. In situation 2, Henry just takes Dombrowski’s word that these are smart moves, possibly with no long term ramifications beyond continued dominance of MLB. And Henry, who is running other business ventures as well, just says “Sounds good. Go with it” while paying less attention than taxes in Guam. And after Dombrowski sprints from the room to execute his plan, I picture Henry snapping out of his business coma to say “Wait. Did I just approve spending $68 million dollars on a pitcher whose had two Tommy John surgeries before turning 30?”