In the NBA, as in life, one of the hardest things is knowing when to say goodbye.

No team likes trading their best player. It’s an admission of defeat. It’s a way of saying “we know we’re not good enough, so we have to go back to the drawing board”. At the same time, sometimes acknowledging that can be the smartest move an organization can make.

The Raptors don’t necessarily need to say goodbye to Pascal Siakam. They made the playoffs in 2021-22 as the fifth seed. At the same time, they could determine that their long-term ceiling is higher if they flip him for the right assets.

On the other hand, the Knicks almost certainly need to wave goodbye to Julius Randle. Their 2021-22 season was a massive disappointment.

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Randle appeared to be at odds with the front office and coaching staff at various points throughout the year.

If both of these teams are ready to say goodbye, could they make a deal with each other?