It's different every year. Last year he thought he could control the market because he had so many players. In 2023 he had two of the four shortstops but the Phillies and Cubs were quick to get the ones he didn't have so he had to proceed (and then the Correa thing went sideways twice anyway). In 2019 it was clearly a competition between not only Harper and Machado but Boras and Machado's agent.
He's certainly been burned before. Arrieta was an earlier example, and so was Kyle Lohse.
I think Soto is also the one calling the shots here. He wants to be done.