Blazers Might Have Blown Damian Lillard Trade, Say Experts

Did Portland whiff on flipping its best player in a generation?

Jan 31, 2024; Portland, Oregon, USA; Milwaukee Bucks guard Damian Lillard (0) steals the ball away from Portland Trail Blazers guard Malcolm Brogdon (11) during the second half at Moda Center. Mandatory Credit: Troy Wayrynen-Imagn Images / Troy Wayrynen-Imagn Images

Did the Portland Trail Blazers get back enough in their deal to move off the contract of frustrated All-Star point guard Damian Lillard in 2023?

That's the question that has been dogging both the team's front office and its fans in the intervening year. Lillard, now 34 and an eight-time All-Star, was shipped off to the Milwaukee Bucks, who fired first-time head coach Adrian Griffin midway through the season and failed to advance to the second round of the playoffs as their aged core succumbed to injuries. The team has since brought in reinforcements this summer in guard Delon Wright, forward Taurean Prince, and most notably former Blazer Gary Trent Jr., who will now once again join his former teammate Lillard in the backcourt as the Bucks' projected starting shooting guard.

On the Blazers side, of course, the move was all about maximizing the asset that was Lillard. As part of a three-team deal, the Blazers added All-Star guard Jrue Holiday and an unprotected 2029 Bucks first round draft pick, pick swap rights with Milwaukee in 2028 and 2030, plus center Deandre Ayton and then-rookie forward Toumani Camara from the Phoenix Suns. The Blazers shipped out former starting center Jusuf Nurkic and former reserves Nassir Little and Keon Johnson. The Bucks flipped swingman Grayson Allen to the Suns in the deal.

Holiday, of course, wound up not playing a single game for Portland. The win-now All-Defensive 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 obtained the Warriors' first round pick in 2024 plus an unprotected Celtics first round pick in 2029.

This offseason, Portland flipped Brogdon, that 2024 Warriors first round pick (which wound up becoming the No. 14 selection in the draft, used on Pittsburgh's Bub Carrington), the second-most favorable of the three 2029 first round draft picks Portland now controls (their own, Boston's, and Milwuakee's), and two second round draft picks in 2028 and 2030, to the Washington Wizards in exchange for expected starting small forward Deni Avdija. The 6-foot-9 former No. 9 pick in the 2020 NBA Draft, Avdija finished sixth in Most Improved Player voting for his efforts in 2023-24.

All told then, the Blazers now have essentially one bonus first round draft pick in 2029, two Bucks pick swaps, Camara, Ayton, Williams, and Avdija, and are now out two second rounders. If the team can offload Ayton and Williams for first round picks, the Lillard deal's ultimate value could improve, but right now, it's not looking so great. Ayton's pricey sticker tag for the next two seasons (he was inked to a maximum deal while with Phoenix) could impede teams from dealing for him.

In a fresh episode of their essential podcast "Blazer Focused," The Oregonian's Aaron Fentress and co-host Craig Birnbach unpacked why the deal is looking worse for wear one year later.

"[...It's] already looking like a pretty weak haul for Lillard, that everyone praised and jumped up and down for, but now, you gave Brogdon and two of their first round picks for Deni," Fentress said. "A player better than Deni and two firsts for Deni. One first left from that and two swaps, and you have Ayton, you got Camara — that was nice, okay — you got Williams. You trade Ayton for just 'stuff,' then the whole thing falls apart, which is what I've been saying from Day One. Even if Ayton pans out, you could've had Ayton, and kept Dame. But if Ayton doesn't pan out, the entire thing falls to pieces."

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