The only answer is Mobley/Garland but Cleveland would never do that deal. Mobley is young and has MVP potential.
Cleveland would never in a million years under any circumstances give us Mobley for Dame. Not even if Sharpe was thrown in.
simons, thybulle, brown, grant & nurk play-in team at least, brown is not better than dame obviously, but it would balance the roster and we would get someone else for dame, celtics have really good role players (grant williams, derrick white, marcus smart, malcolm brogdon) although playmaking would be a bit of an issue (ant looked nice last season when he played like pg insted of sg), but hes not there just yet, we would likely need backup pg
looking around the league for fitment and history, i could see toronto and masai looking at an all in with dame as a trade partner. he did it with leonard and won a chip, might see dame in the same light. they will have van fleet and trent opt out for free agency clearing out much of dames salary and opening up the PG spot and shot opportunities. like us looking to acquire siakim, i could see the roles reversed. the raptors send out a package that would feature OG whom @ 25 would fit a blazer rebuild age wise, boucher and young for salaries along with precious achiuwa as a prospect and picks and pick swaps for the foreseeable future to try and justify it from our perspective. i do not advocate the trading of our generational talent at all. just a mental exercise of who might be interested as a trade partner and a possible return. i in no way think it is equal value, but it seems realistic considering the value the league is placing on 2 way wings and mobile bigs..
If Portland was lucky enough to get the #1 pick, I think you have to go with Wemby and if Dame things that is a rebuild, do your best to get him to a good situation while getting significant draft assets/young pieces to move forward. Who knows how Wemby will turn out, but I think you have to take that chance on a generational type of player with that size and ability. It's unlikely to happen and much more likely we get a lower pick and combine that with other assets to try to bring in more talent, but I fear that will gut the future of the franchise. I don't believe we could get anyone significant enough to make a difference and the Draft picks we would give up could be very valuable as they may be coming do as Dame is winding down his career.
Jody, Bert, Joe & Chauncey will have to either orchestrate a significant trade involving picks and players to convince Dame things will improve, or, chances are Joe will convey to Dame it may be best for all to find a trade. Joe will be wanting to keep his Job, so this off season will be the deciding factor if he has a shot too or not. If he's not able to significantly consummate a block buster that makes a difference or not, What Happens?