There are only two ways I could see Caleb ending up a Cowboy.
Option A - He enters the draft, warns the Cardinals (or Bears) not to draft him, they draft him anyway, and his agent gives said team this same list of teams. The Jones would have to make a blockbuster package BUT it would be doable since said team has very little leverage. Caleb can simply not play for them so they will have to deal him.
Option B - He returns to USC for 2024 AND Dak misses next year due to injury or contractual reasons. Cowboys stink it up and finish with a record at least clos enough to move up to #1 in the draft.
Both are highly unlikely.