Sometimes in football a draw makes both teams winners. Say Juve-Roma in the last round of serie A, where a draw would make us win the scudetto and Roma secure the 4th spot for the CL. Or Denmark-Sweden in 2004
I believe that both Marotta and Leonardo left the meeting with a big smile. Not for defeating the other guy, but for the good deal they made for their own club.
We put a guy on the transfer market and sold him for the asked money (yeah, the option is just a formality in Higgy's case). Milan got a super striker which can take them to CL. We got back a guy we never wanted to leave in first place. And none less but an instrumental player in our WC defense. Milan replaced a player who was going to leave anyway, with a young potential.
Sure, we can never know what the future brings. In a month from now some of these 3 might break a leg. Higuain could score a goal that will cost us a title. Caldara could become a Ranocchia. Bonucci could become a shadow of his former self.
Or maybe Bonucci can be vital in a CL winning defense, Caldara will become a great Italian defender, or Higuain will score goals that will win Milan a CL spot or titles.
The probability is, though, that both teams will benefit a lot from these transfers and they'll both feel like winners for years to come. This won't be a Pirlo for Brncic exchange Milan and Inter did in 2001.