I'm having trouble figuring out how we get much value out of either KP or Jrue, the two most tradable players. We are essentially forced to trade at least one of them, which doesn't put us in the best of bargaining positions. Holiday has 3 more years (player option 27-28), so we would have to find a win-now team that is also willing to hold onto a contract that will increasingly suck at an exponential rate. At least with KP, he's an expiring contract next year, so we might as well hold onto him until the trade deadline and hope that he is healthy. We'd be selling very low on him right now.
I'm not excited about the idea of trading Jaylen Brown simply because he is our best chip right now. We wouldn't get close to fair value for him, and that would leave us with Jrue, Derrick and Porzingis all in the early to mid 30s by the time Tatum got back, without much in the way of a youth movement.
I'm hoping Brad can work his magic, but it could be a really tough few years.
Mike