Over the weekend, Yahoo Sports’ NBA insider Chris Haynes reported on the possibility of Damian Lillard requesting a trade out of Portland this offseason, suggesting that recent events surrounding the team’s hiring of Chauncey Billups and concern over the front office’s ability to build a contender are forcing him to contemplate his future with the franchise.
The backlash from Portland Trail Blazers’ coaching search and his concerns over whether a championship contender can be built have become major factors that could force Damian Lillard to request out, league sources tell @YahooSports. https://t.co/syN8upvWPx
— Chris Haynes (@ChrisBHaynes) June 27, 2021
The Sixers are strongly positioned to pursue Lillard—both in terms of being a desirable destination, and having the assets required to put together a desirable package—and trade speculation naturally spiked in the hours since that report. After crunching the NBA Trade Machine and considering every possibility available (spending more time than I care to admit) here’s what I came up with:

Why the Sixers do it?
Sixers give up: Tobias Harris, Tyrese Maxey, Matisse Thybulle, Seth Curry, 28th overall, 2023 1st Rd, 2023 2nd Rd (ATL/BK/CHA best), 2026 1st Rd
Sixers receive: Damian Lillard and Kevon Looney
Damian Lillard. Plain and simple.
The majority of trade packages I’ve seen involve sending back Ben Simmons, but Morey ought to make every attempt to add Dame without including him, and this package is as close as he’ll get.
Why Golden State does it?
Golden State gives up: James Wiseman, Andrew Wiggins, 7th overall (from MIN), and Kevon Looney
Golden State receives: Tobias Harris and Jusuf Nurkic
With an aging yet high-end duo of Curry and Draymond, and a hopefully fully-healthy Klay Thompson returning next season, the Warriors are in win-now mode. Upgrading from Wiggins and Wiseman to Tobias Harris and one year of Nurkic is a strong move that solidifies their starting five, but is it worth the 7th overall pick (from Minnesota) in this years draft? I’d say so, though I wouldn’t disagree if you think they need more sprinkles here.
Why Portland does it?
Portland gives up: Damian Lillard
Portland receives: James Wiseman, Tyrese Maxey, Matisse Thybulle, Andrew Wiggins, Seth Curry, 7th overall pick, 28th overall pick, 2023 1st Rd (PHI), 2023 2nd Rd (ATL/BK/CHA best), and 2026 1st Rd (PHI)
Wiseman, Maxey, Thybulle, and this year’s 7th and 28th overall picks is a strong base for a rebuild. Curry is a flippable asset who should draw a mid-to-late first (at least) from a contender over the next half year, and that value is factored in here. Wiggins has some value to be flipped to a team who wants to replace a terrible contract on their books with a still-bad contract yet decent player in Wiggins, with the idea that they’ll need to attach an asset of modest value (a few seconds, maybe late-first) in return. Add in the 2023 unprotected first from the Sixers, the 2023 most favorable second (BK/CHA/ATL), and the unprotected 2026 first, and it’s hard to knock this package.
From Portland’s perspective, that’s a decent mix of present and future draft picks to go along with a few young players who have real talent. They’ll easily be able to add to that stockpile by flipping Wiggins and Curry, along with whatever they get in return from future McCollum and Covington deals.
At a glance it looks like the Sixers might be giving up a lot here, but in the context of adding Damian Lilliard (all four years of his contract) and retaining Simmons, it’s nearly impossible to overpay. If Morey needs to offer a blank check and sell the farm to make this a reality then so be it.
What would the Sixers new rotation look like?
Starting 5:
- Damian Lillard
- Danny Green
- (Mid-level Exception) Bullock? Batum?
- Ben Simmons
- Joel Embiid
Bench:
- George Hill
- Shake Milton
- Dwight Howard/Kevon Looney
- Furkan Korkmaz*
- Isaiah Joe
- Gary Clark
*If Korkmaz isn’t priced out of the Sixers early bird rights (roughly $10-12 mil. AAV), and if ownership is willing to foot the increased tax bill, then Morey needs to retain Furkan in this scenario
The Sixers shouldn’t have trouble attracting a 3-and-D wing to fill out their starting lineup on the MLE (roughly $5-6 mil. AAV), and Hill/Milton is a nice mix of shooting/playmaking off the bench. If the team wants to bring back Howard they can, but Looney is a capable backup big if need be. Bringing back Korkmaz is obviously more important in this scenario given how thin the Sixers would be, but it won’t be hard to find cheap replacements on minimum contracts if Morey has to.
We can debate the lack of depth all we want, but the NBA is ultimately about top-tier talent, and this lineup undeniably improves the Sixers in that department.