I don't like Dombrowski's 'win at any cost' philosophy, as you well know, but if the Sox don't advance in the playoffs, it won't be Dombrowski's fault. He put together a team that's not just good enough to win it all, but one that is arguably better than any team in the playoffs, save for maybe the Astros, and arguably one of the best teams in Red Sox history.
That said, if we do get eliminated, this will be Exhibit A as to why it's not a good idea to follow that 'win at any cost' philosophy.