Sometime between Dec15 and the trade deadline, when NBA FO phones start ringing again...
Toronto discovers you can't replace Vanvleet with Schroder, and they're a few games outside of the play-in.
Miami is leading the play-in, a game or two behind the 5th and 6th seeds. They realize that Jaquez Jr is too young to close games at the 4, Jimmy's too old, and Caleb's too small.
Toronto would love to extend OG at half-max value, but he wants more. Especially with Toronto's/CA taxing situation. They also don't want to lose him for nothing. Replacing him with a cheaper Caleb, assuming he gets full mid-level money, and picking up draft capital would be prudent.
Miami would hold firm at that half-max number of $112M/4yrs. With another postseason run plus SouthFL living, OG could accept it. OG essentially replaces Lowry's cap number, and losing Duncan's gets us out of the tax in the summer of 2024.
Lowry or JRich / JRich or Lowry
Butler/ Herro
O.G./ Jaquez Jr
Love or Jovic/ Porter Jr or Highsmith
Adebayo/ Bryant or O. Robinson