This trade proposal is based on a similar proposal by Gabriel Coelho in his article,"4 Teams that should trade for Tyler Herro." This proposal is also similar to a Fanspo proposal made by @Kairon.
On August 2nd, 2005, the world forever changed. Pat Riley organized a five-team, thirteen-player trade, a signature moment in Miami Heat history, which eventually led them to winning their first NBA championship.
This proposal would also be another record setting blockbuster, potentially involving five teams and 21 players. This trade adds a feather to Lillard's hat, adding to his legacy involvement in a new NBA record setting trade.
Why the Trailblazers do this:
Dame wants out, but Scoot Henderson, Anfernee Simons, and Shaedon Sharpe will still make up a small backcourt. The Trailblazers cannot take a gaggle of talent in exchange for Damian Lillard. The Heat can gather some assets that match Dame's contract but not the Blazers' lineup, nor Dame's talent. Thus, this trade allows the Trailblazers to acquire talent while sending Damian to a contender, hopefully to compete in the NBA Finals.
Additionally, Jerami Grant will likely be traded at the 2024 trade deadline, and the Trailblazers could offer a package that includes Grant and Hayward. Might New Orleans or Cleveland be interested in Grant and Hayward?
Why the Heat do this:
Damian is the best clutch shooter in Trailblazers' history. If Miami finds themselves down two points before the end of regulation, give Dame the ball. By sending their tradable assets to other teams, which gets the Trailblazers the talent and size they need, Miami creates a win-win solution for both franchises.
Additionally, this proposal reunites the Martin twins in Miami.
Why the Hornets do this: Gabriel Coelho explains it best:
"The selection of Alabama’s Brandon Miller with the No. 2 pick and the returns of Ball and Bridges should lead to a better season in Charlotte, but there are still obvious questions about the roster.
Finding a backcourt partner for Ball remains a priority. Rozier is entering his 30s, former lottery pick James Bouknight hasn’t shown much upside in two seasons, which led them to select Nick Smith Jr. at the end of the first round. But this team should try to be more competitive right now. That’s where Herro enters."
In my proposal, Tyler Herro is joined by Duncan Robinson, Nikola Jovic and Haywood Highsmith, adding depth at the #3 and #4 positions, which would be lost with Gordon Hayward, Mark Williams and JT Thor going to Portland.
Why the Pacers do this: The Pacers recently drafted Jarace Walker, while possessing several frontcourt players - one of whom will be cut. However, to move into contention, they need to improve at the #3 position. Adding Nassir Little to their roster potentially fills that gap. All they need to do is give up some of their youthful depth. (https://fansided.com/2023/05/23/pacers-2023-offseason-primer-targets-free-agents-trades-draft-needs/).
Why the Thunder do this:
For Miami to get Damian Lillard, they need to send five picks to Portland. I know many of you will argue with me about the number of draft picks, but Joe Cronin has made it clear, he won't accept less than four picks. Plus, the local media in Portland wants nothing less than Miami's best offer, which could include another pick that Oklahoma currently possesses. If Miami sends a 2ndrp + a more favorable FRP pick to Oklahoma, I believe the Thunder will send the unprotected '25/'26 pick to Portland.