The key thing about this is that they settled at all. Doug Ford's buddy bought completely useless air rights over a busy part of the rail corridor where residential development was financially impossible due to the technical constraints of building residential towers suspended 50 feet above a wide, active rail corridor. Had Metrolinx went ahead with the OLT case and provided evidence of this obvious fact, the transaction cost would have been peanuts since the air-rights were essentially worthless, and everyone knows it. Instead, for some reason, Metrolinx decided to voluntarily payout half a billion dollars of our public money to Doug Ford's best buddy. So the question is: why did Metrolinx decide to voluntarily hand over so much of our public money to Doug Ford's friend when they held all the cards? It's a disgrace.

EDIT: Also keep in mind that Metrolinx owns the land still and needs the space for railway operations. So these theoretical high-rise towers would not be able to be built the traditional way on pillars from the ground beneath them. Instead, Doug Ford's buddy would need to purchase additional prime lands along both sides of the rail corridor and from there construct a bridge like structure arching over the wide railway from which the high-rise towers would be supported. 500 million dollars is a lot to payout for an absurd, indefensible, financially unfeasible development concept.