I just don't put much stock in anybody's public statements. Klentak likes to play things close to the vest. Middleton also put him in a dumb position with the "little bit stupid" comment. But they know that preparing the fan base in advance for failure won't actually work, just like statements in the media won't actually affect negotiations tangibly (Scott Boras: "oh, Matt Klentak says he doesn't want to go crazy, I guess I'll take his lowball offer and assume
he won't go higher"). It just doesn't really tell us what's going on.
And while I do think an owner should let their president and GM do their jobs, he's still the owner, he's going to be directly involved in negotiations at this level, and if MacPhail and Klentak are too conservative for his taste he will likely overrule them. Which he arguably already did with Arrieta even if the market came to them.
If the gulf between the Yankees and Phillies really is 30-50 million, or if Machado suddenly decides he wants to play with his brother-in-law badly enough to take a lower offer from the White Sox, well, at least we didn't trade for him last deadline. At that point, of course, you have to be willing to go bigger on Harper.
As leak-happy as this business is we haven't heard news of a single tangible $ offer to either player, from any team. Everything is speculative.