Last summer, the Portland Trail Blazers had one of the most significant offseasons in franchise history. After the Blazers officially landed the No. 3 overall pick in the lottery that summer, there was much discussion surrounding what general manager Joe Cronin would do with their pick.
Lillard seemed willing to remain loyal to the franchise he spent his entire career with and a city that he has a lot of personal investment in and ties to, but only if the Blazers made an aggressive move to surround him with established players who were ready to win-now and give him a reasonable chance of making a deep playoff run.
Revisiting the Blazers' Damian Lillard deal
Instead, the Blazers took the opposite approach, selecting Lillard's replacement in No. 3 overall pick Scoot Henderson and trading Lillard to the Milwaukee Bucks, pairing him with superstar Giannis Antetokounmpo to give him at least a chance at winning a championship. Here is the breakdown of that deal:
Bucks received:
- Damian Lillard
Blazers received:
- Deandre Ayton
- Toumani Camara
- Jrue Holiday
- 2029 1st-round pick (via Bucks)
- Two first-round pick swaps with Bucks (2028, 2030)
Suns received:
- Grayson Allen
- Keon Johnson
- Nassir Little
- Jusuf Nurkic
It was hard to see Lillard leave Portland, but an offseason later, and it still seems like the right decision for them to embrace a rebuild. Even if the Blazers did trade the No. 3 pick for a veteran to get Lillard help, they still likely wouldn't have had enough to be considered legitimate contenders.
Additionally, a recent CBS Sports article in which Sam Quinn ranked all 68 traded future NBA first-round picks makes the trade look even more promising for the Blazers.
Blazers' picks from Lillard deal ranked inside CBS Sports' top ten
All three of the first-round picks (two of which are swaps) that the Blazers received from the Bucks are ranked in the top ten by Quinn. The Bucks' 2028 pick comes in at No. 9, the 2030 pick at No. 7, and 2029 is ranked as the top traded future NBA first-round pick. It's worth noting that the 2029 deal could belong to either the Blazers or the Wizards. Portland sent Washington the second-most favorable of their first-round picks as part of the Deni Avdija deal.
It's somewhat shocking that the Bucks' picks are so highly coveted, but Quinn mentions the Bucks' potential inability to pivot away from an aging roster. Milwaukee has one of the shallowest benches in the entire league and a starting lineup that includes Lillard (34), Khris Middleton (33), and Brook Lopez (36).
The timing could work out well for the Blazers. Portland's young core should be much more developed by the time these Bucks' picks come around, which will be especially important with the pick swap in 2029. If Milwaukee struggles by then, as Quinn predicts, the Blazers must put together a competitive roster by that point; there would be no incentive for them to get another lottery pick if they lose it to Washington regardless (assuming Boston is still ahead of Milwaukee and Portland at that point).