He has the same problem all authoritarians do: he is surrounded by idiots who lie.
He likely doesn't know exactly what is happening because the people around him are incompetent and constantly lie telling him what he wants to hear. And his immediate underlings have the same problem. And so do their underlings.
The US can't have a coherent strategy because the principle decision makers are both misinformed and constantly lying.
An authoritarian who had a fully functioning brain would at least be able to sort out the lies and spin, but Trump can't do that any more.
That news media have published "peace deal any day now!" for over a month really hammers home both their cowardice and incompetence.
This is easily a defeat many times worse than the withdraw from Afghanistan but its being covered like an imminent victory by the media. When the US withdrew cable news had this 24/7 parade of generals explaining how they TOTALLY won the war and its just a mystery how things turned out how they did and it must have been a Biden fuck up, despite it being a deal signed by Trump. But now with
Iran pulling out of negotiations the media is still
willingly republishing "victory any day now!".
They've learned nothing from 2003.