One of the things that isn’t be said enough is that the president is really bad at making deals and really bad at recognizing when there is a deal to be made.
The democrats would like a path to citizenship. They would like to fully fund the ACA. They would like infrastructure bills. They might be willing to offer something on the wall for any of these. But we all know no deal can be made. His base is not ok with the ACA or a path to citizenship and they never cared about an infrastructure bill.
So he went into a negotiation asking for something that couldn’t be given to him and without anything to offer in return.
This isn’t what a master deal maker does.