I think a lot of chess is going on here
Dana's fluffing up Jon while secretly telling Aspinall to provoke him. He now knows that gaslighting Jon into a fight like he usually does with fighters won't work like it didn't with Francis. As such, he's employed a new strategy. On the other hand, Jon wants a 15-20 million dollar payday for Aspinall (which I personally wouldn't have a problem with him getting), and so he keeps talking retirement to scare Dana into conceding. Very interested to see how this all plays out. I definitely want this stupid Stipe fight to be over with though.