You make a compelling case, OP, at least to the Leafs and to Chicago. Not to Tavares, whose certain veto is all that matters, of course.
He wants to be in Toronto and to take another swing there at a title. He leaves now for the Blackhawks, and he might never land on a contender again. He stays, and he could have a strong resurgent year, help them to better playoff fortunes in Spring 2025, and earn another contract from a contender - if not Toronto, then someone else. He can't do that on a cellar dweller.
Why voluntarily leave a good team for a bad team? Why do that when you don't have to, and he doesn't have to... it doesn't make sense for the player.
If you flip this around and ignore the teams' wishes, it does not take long to figure out that you don't need to find a bad team. You need to find an off ramp to a good team, with as good or better chance to win as Toronto.
JT isn't waiving to go to a worse team, and has an $11M AAV. That's why by far the likeliest outcome is that he remains a Maple Leaf.