Celtics need to stop chasing guys who are already established and starting getting guys on the upswing. Christian Woods is one of those players. He has a cheap contract and he's trapped on a rebuilding team. He's an agile, athletic big, who can shoot as well as drive the ball. I'd trade TimeLord, Nesmith, a protected 1st for him. I don't think resigning him would be an issue and he fits with the Jays timeline.
You realize there is a contradiction in your thought pattern here, right? Christian Wood, young guy on the upswing, but you want to trade Timelord to get him, an even younger guy on the upswing.
Wood fits into out TPE, so that and two picks(1st and a highly protected 1st that converts to 2 seconds). Or Juancho, Freedom and Nesmith with a first works also. Two expiring contracts, a prospect and a pick seems reasonable.
If Wood goes on the block though, I imagine those things won't be enough. Several playoff bound teams will be jumping all over the place in a bidding war for Wood.
I think Houston needs value that's where TimeLord comes in. I don't think we can get woods with just throw ins and I don't want to give up too many 1sts. Woods is probably leaving Houston by trade or next contract for a better situation, Timelord is locked in. I also think what Woods would be more dependable and consistent with TimeLord and I think he has borderline all-star upside ala Randle.
I think, long term the goal would be to have Wood play alongside Timelord , as Wood can play the PF/C position much like the way the team is using Horford. Adding him I think sinks our future picks into the mid 20's. For that reason, in a bidding war, I would have zero issue trading picks. Time to secure high quality vets and get out of the developing youth business.
I can understand people's desires to keep picks, but recent world champs didn't get there by developing youth for a decade or more. They got their through trades for superstars, stars and high quality vets. With what's looking like two excellent home grown superstars(Tatum, Brown) and three extremely solid/important home grown rotation pieces(Smart and Grant and Robert Williams), it's time to get into the acquiring high quality vets business. JRich was a good pickup. Cashing in youth and picks for Wood would be the right move as well, IMHO.
Cashing in picks isn't going to kill the Celtics because their core is so young. This isn't a Laker or Brooklyn issue where the core is much older and the lack of picks will decimate the team in a few years when the old guys wear down or retire.