Must say that this was one of the most thought provoking posts I have come across on this forum👏
Your mention of that Matrix sequence was very apt. In fact I got reminded of another sequence where Neo questions Oracle if she already knew that he was going to accept the offered cookie then it wasn't much of a 'choice'. And she said-" You are not here to make a choice. You have already made it-you are here to understand why you made it."
Though I admit I do not completely grasp this, intuitively I think it refers to the inherent nature of the person making the choice, which is what determines his choices. So there is free will and there is an illusion of free will as well. For as the Gita mentions the three Gunas control our conduct, as long as we are a slave to it or bound to it, free will will remain an illusion for our choices are already determined by the composition of our nature even if not destiny. So it is only when one rises above this-when attains contact with his true inner being and transcends the limitations of his nature can one really be out of the web and free to make choices.
So even if Duryodhan's choices was not determined by any higher Power, his weakness and limitations of nature had his fate sealed and future determined.