The Damian Lillard saga has been at a standstill for months. He requested a trade from the Portland Trail Blazers on July 1st, with subsequent reporting indicating the eight-time All-Star hoped to be moved to the Miami Heat. No other serious suitor for Lillard has materialized in the interim. Still, with training camp for the 2023-24 season right around the corner, Lillard remains in Rip City.
But Miami isn't the only team initial reports suggested Lillard wanted to play for. He also expressed interest in the Brooklyn Nets, but there hasn't been much activity on that front, either. The Philadelphia 76ers are eyeing Lillard as part of a trade involving disgruntled star James Harden, though that potential trade—surely involving at least one additional team—would be tough to pull off. Fortunately for Portland, another team has reportedly thrown its hat in the ring for Lillard: The Chicago Bulls.
The Bulls are an interesting wild card in the Lillard sweepstakes. Zach LaVine has been mentioned as the likely centerpiece of a possible deal between Portland and Chicago. Bringing in Lillard would make all the sense in the world for the Bulls, stuck on the treadmill of mediocrity with a veteran roster that just finished 40-42 a year ago.
While Chicago wouldn't be a top-tier contender with Lillard in the fold, Billy Donovan's team would certainly be more of a threat in the Eastern Conference. The question is whether the Bulls can produce an offer for Lillard that makes the Blazers finally pull the trigger on a trade. What could that Lillard-to-Chicago deal look like?
Perfect Damian Lillard trade Bulls must offer Blazers
Chicago Acquires: Damian Lillard and Jusuf Nurkic
Portland Acquires: Zach LaVine, Patrick Williams, Dalen Terry, Andre Drummond, 3 first-round picks (2024, 2027, and 2029) and 2 first-round pick swaps (2028 and 2030)
It's easy to see how this trade makes sense for the Bulls: They're the ones getting Lillard, who is at minimum still a top-15 player in the NBA.
Portland will want to shed salary and the Bulls must oblige. They do so in taking on Nurkic, who's owed more than $54 million over the next three seasons. He and Lillard combine to make more than $207 million through 2025-26, and the latter has a $63 million player option on his current contract for the following season.. The Bulls' ownership group isn't exactly known for big spending, but getting Lillard requires a massive financial commitment.
It's unclear how Portland would view this trade. Like other trade packages involving teams who want Lillard, acquiring LaVine, another guard not known for his defense, isn't in the Blazers' long-term best interest. Scoot Henderson, Shaedon Sharpe and Anfernee Simons are all cut from a similar cloth for now, and while all have the talent and skill sets to play together, adding LaVine to that mix would only add to Portland's redundancy on the perimeter.
But Portland also could just make another trade down the line, whether it involves LaVine or Simons. And for all of LaVine's flaws, the guy can really score. Among players who played at least 20 games last season and had a usage rate of at least 27%, only 11 players had a higher effective field goal percentage than LaVine's 56%, according to NBA.com. Only 12 players had a better true shooting percentage than LaVine's 60.7% mark. LaVine being from the Pacific Northwest (Renton, Washington) can't hurt matters either.
Patrick Williams and Dalen Terry shouldn't get overlooked, either. The No. 4 overall pick of the 2020 draft may not live up to lofty Kawhi Leonard comparisons, but Williams upped his shot volume without sacrificing much efficiency last season and is already a stout, versatile defender at 6'8, 215 pounds. There is still a lot of upside to work with there. The same can't be said for Terry, but stocking up on rangy wings who can defend is never a bad idea, and Terry fits that bill. He isn't much of a shooter yet, but offers an extra playmaking dynamic that could work with the Blazers' staple of young guards.
The real prize here is the bounty of first round picks that Portland is getting. Three unprotected firsts and two unprotected pick swaps are what every team wants. Getting those from a less than stable organization like Chicago could be a massive coup. Lillard just turned 33 years and DeMar DeRozan just turned 34—they'd be a couple years from 40 once most of these picks convey. Betting against their age and the Bulls' franchise seems like a worthwhile trade for the Blazers if the opportunity presents itself.