He either doesn't understand, or doesn't care.
You can literally sign every big name free agent in every offseason and still not win the WS. The goal should be to contruct a team that has the ability to make the playoffs every year, because we all know the playoffs are a crapshoot once you get in. Going "all in" for a 1-2 year shot at a WS title is not smart. It never works out. But these people that complain haven't been following baseball long enough to know that.