How is it a silly game? It seems a sensible thing to do from his point of view. He’s had a successful year last year and now wants to see how the Season starts off before making a decision about tue next step in his career. And is it possible to “find yourself sold”? Doesn’t he have to agree to go?
You outline the scenarios above and while they might be possibilities it’s also equally likely that, were he to extend his contract right now, he could end up not playing and nobody will buy him because the price goes up due to his longer term contract. Sure, it could blow up in his face but it just sounds like he’s being prudent at a pivotal moment in his career.