Have the Portland Trail Blazers recouped enough money in their contract to get rid of frustrated All-Star point guard Damian Lillard in 2023?
It’s a question that has been plaguing the team’s management and fans for the past year. Lillard, now 34 and an eight-time All-Star, was sent to the Milwaukee Bucks, who fired new head coach Adrian Griffin midseason and failed to advance to the second round of the playoffs as their aging core succumbed to injuries. The team has since brought in reinforcements this summer with guard Delon Wright, forward Taurean Prince and most notably former Blazer Gary Trent Jr., who will now join his former teammate Lillard on the back end as the Bucks’ projected starting guard.
For the Blazers, of course, the move was meant to maximize Lillard’s asset. In a three-team deal, the Blazers added All-Star point guard Jrue Holiday and an unprotected 2029 first-round pick from the Bucks, rights to swap picks with Milwaukee in 2028 and 2030, and center Deandre Ayton and rookie forward Toumani Camara from the Phoenix Suns. The Blazers sent former starting center Jusuf Nurkic and former backups Nassir Little and Keon Johnson. The Bucks traded wing Grayson Allen to the Suns as part of the deal.
Holiday, of course, didn’t play a single game for Portland. The All-Defensive point guard was traded to the Boston Celtics. Portland received then-reigning Sixth Man of the Year Malcolm Brogdon and All-Defensive center Robert Williams III, but more importantly, the team also got the Warriors’ 2024 first-round pick as well as an unprotected 2029 first-round pick from the Celtics.
This offseason, Portland traded Brogdon, the Warriors’ 2024 first-round pick (which ended up being the 14th overall pick, used for Pittsburgh’s Bub Carrington), the second-best of the three 2029 first-round picks Portland now controls (their own, Boston’s and Milwaukee’s), and two second-round picks in 2028 and 2030, to the Washington Wizards in exchange for expected starting wing Deni Avdija. The 6-foot-1 former No. 9 overall pick in the 2020 NBA draft, Avdija finished sixth in Most Improved Player voting for his efforts in 2023-24.
In total, the Blazers now essentially have a bonus first-round pick in 2029, two pick swaps from the Bucks, Camara, Ayton, Williams and Avdija, and are now without two second-round picks. If the team can get rid of Ayton and Williams for first-round picks, the ultimate value of Lillard’s contract could improve, but right now, it doesn’t look so good. Ayton’s high price tag for the next two seasons (he signed a max contract while with Phoenix) could prevent teams from trading him.
In a new episode of their essential podcast “Concentrated Blazer” The Oregonian’s Aaron Fentress and co-host Craig Birnbach explained why the deal looks increasingly bad a year later.
“[…It’s] “It already seems like a pretty weak haul for Lillard, who everybody praised and jumped up and down for, but now you give away Brogdon and two of their first-round picks for Deni,” Fentress said. “A player better than Deni and two first-round picks for Deni. A first-round pick went from there and two trades, and you got Ayton, you got Camara — that was nice, okay — you got Williams. You trade Ayton for just ‘stuff,’ and then it all falls apart, that’s what I’ve said since Day 1. Even if Ayton succeeds, you could have had Ayton and kept Dame. But if Ayton doesn’t succeed, it all falls apart.”
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