We actually had more than clues before Kennedy became the CEO. Now its unclear at least to me whether the Pres of Baseball Ops makes his case to Kennedy and then its Kennedy that decides if he will take major signing's to Henry himself for Henry's approval or if the CEO brings the Pres of Ops along and allows him to make his case in person.
Based on what we "knew" before Kennedy became CEO, it appeared obvious that the Pres of baseball ops (or GM if there was nobody titled as Pres of Ops) would go directly to Henry to get final approval for high ticket contracts with Larry Lucchino along for the ride while he was around, throwing his weight one way or the other.
We also no longer know where the cutoff is in a definition of a signing as high ticket.
I would think that the organization would have had to go to Henry for a final approval on the Sale extension but not the Eovaldi or the Pearce signings. To be clear, keeping ownership in the loop is not the same thing as seeking approval for a big deal. I would expect the owner to be kept in the loop for Major League signings....all of them.
This is not to say that rejecting a proposal for a high ticket contract from the organization to the owner in this town is an easy decision to come to. NOT IN THIS TOWN.
Lets say Henry rejected the Sale extension. Does anybody think that would not have gotten out in the media eventually and picked over in painful detail if that went wrong?
If it were me in Henry's position, I would have preferred that my Pres of Baseball Ops and my CEO figure out that the Sale extension in light of his issues with wear on his arm and his recent late season issues was premature and whatever money it cost to let the 2019 season play out was better than being stuck with that contract for 5 years given that better information, more complete information was only months away.