To be fair, as much as Lucchino knows about baseball, his main purpose behind baseball moves was putting fans in the seats. The way a baseball ops persons builds a team (to get the most wins) is different than the way a businessman builds a team (to make the most money). Sometimes, those two ideas are not mutually exclusive, but many times they do not mesh.
The moves that I blame Lucchino for are the types of 'splashy' or 'sexy' moves that just do not make any sense from a baseball ops point of view, especially one that is advanced metrics oriented. Pablo is Exhibit A.