Grade the trade: Blazers spurn Heat, deal Damian Lillard to Eastern rival

July 1 marked the end of the Damian Lillard era in Portland.

The most popular, and arguably the best, player in Trail Blazers franchise history requested a trade away from the only NBA franchise he’s ever known. Whether it was the organization’s fault for not doing enough to keep Dame happy or if building a true contender around a high-usage, small guard who can’t defend no longer matters.

Lillard will be attempting to win an NBA title elsewhere next season.

If he gets his wish, that will be in Miami alongside Jimmy Butler and Bam Adebayo. From a Portland perspective, however, that’s just about the worst possible Lillard destination. If general manager Joe Cronin truly wants to kickstart a rebuild and give the Blazers a real shot at winning a championship down the line sans Dame, it’s his responsibility to get the best and most assets in return for a 33-year-old superstar who proved last year’s he’s still in his prime.

Unless the Heat can find a way to acquire a boatload of first-round picks or attractive young players, that trade could be elsewhere; Cronin has no mandate or responsibility to deal a player of Lillard’s caliber for an underwhelming return just because Dame wants it.

Maybe the two parties can find a compromise. Dame can go to another team that has a chance to make a legitimate title push, and the Blazers can get an acceptable amount of assets to move the franchise forward.

The Trail Blazers should trade Damian Lillard to the Brooklyn Nets, not Miami

The first time Lillard mentioned preferred trade destinations, he included the Nets because of his relationship with Mikal Bridges. With Dame on board, Brooklyn would become an Eastern Conference threat just as Miami is – especially in this deal.

The Nets give up absolutely 0 percent of their rotation. Adding Lillard to Bridges, Cam Johnson, Dorian Finney-Smith, Royce O’Neale, Nic Claxton, Cam Thomas, and Day’Ron Sharpe keeps the core of Brooklyn’s roster intact. The team is losing Simmons, who never played, and the rights to two rookies who have yet to put on a Nets jersey.

Brooklyn also keeps six first-round picks and a swap between 2025 and 2030.

The allure of this trade for Portland is the four future firsts and two high-upside rookies in Clowney – a 18-year-old, 6-foot-10 forward with length, athleticism, and versatility, giving him the potential to develop into an ideal big man in today’s NBA – and Whitehead, a 6-6 scorer and shooter with tremendous offensive upside who only fell in the draft because of health concerns.

The Blazers go all-in on the youth movement in this deal, pairing rookies Scoot Henderson, Kris Murray, and Rayan Rupert with Clowney and Whitehead. That’s five players from this past draft, four of whom were first-rounders.

The four future firsts Portland adds arrive down the line in 2028 and 2029, and three of them come from Phoenix and Dallas, two franchises whose long-term futures are in question. Those picks have the potential to fall high in the lottery and would give the Blazers the chance to add more prospects after Henderson and Co. have had time to develop.

Potential depth chart after Damian Lillard-Brooklyn Nets trade

If this is the route Cronin decides to take, the Trail Blazers are loaded with future assets and a young group of players who can develop together on the same timeline. (Matisse Thybulle has a qualifying offer from Portland but has yet to sign, but he makes sense with this team as a 26-year-old wing. Jerami Grant’s extension is not yet official).

A depth chart would look something like this:

PG: Henderson (19 years old), Anfernee Simons (24), Keon Johnson (21)

SG: Simons (24), Shaedon Sharpe (20), Whitehead (18), Johnson (21)

SF: Sharpe (20), Whitehead (18), Murray (22)

PF: Murray (22), Clowney (18), Nassir Little (23)

C: Jusuf Nurkic (28), Clowney (18)

Along with the four firsts, that’s a massive all-in approach to a youth movement for the Blazers. Only Nurkic, and potentially Grant, is older than 24, and there’s no guarantee both are in Portland long-term.

This seem like a fair compromise for all parties – the Blazers, Nets, and Lillard – and its levels above anything the Heat can offer. Cronin needs to find trades like this rather than settling for a lesser package from Miami simply because it’s where Dame wants to be.