Best Trade Proposal For Bulls To Acquire Blazers’ Damian Lillard

Damian Lillard, Chicago Bulls, Portland Trail Blazers, NBA Trade Rumors
NBA Analysis Network

Early this NBA offseason, Damian Lillard asked the Portland Trail Blazers to trade him after spending 11 fruitless seasons with them. He had professed his loyalty to them in the past, even after one early playoff defeat after another, but now that they have embraced a youth movement, he has realized he needs to go.

His time with them has resulted in a grand total of one trip to the Western Conference Finals, during which they got swept by the Golden State Warriors. At age 33, the clock is ticking louder and louder on Lillard’s chances of ever winning an NBA championship.

The one team he has preferred to be traded to all along has been the Miami Heat, but there has been little, if any progress, on a potential deal with them. Now, the Chicago Bulls are reportedly interested in getting in on the Lillard sweepstakes.

For the last few years, the Bulls have possessed some nice, talented players such as Zach LaVine, DeMar DeRozan, Lonzo Ball and Nikola Vucevic. But it hasn’t amounted to much, as they have made the playoffs just once in the last five seasons.

NBA TRADES, NEWS & RUMORS: Damian Lillard, Portland Trail Blazers, Zach LaVine & Chicago Bulls Updates

Ball’s career appears to be over after numerous injuries, and thus trading for Lillard could be a great idea for Chicago. If it offers the right package, perhaps it could make the race for the Eastern Conference more interesting this coming season.

LaVine’s name has frequently come up in trade rumors, and thus he would be a nice starting point in any trade discussions between the two teams. Add in a nice role player and some draft capital, and perhaps the Bulls could beat any package the Heat have to offer.

The Proposed Trade

Chicago Bulls Receive: G Damian Lillard
Portland Trail Blazers Receive: G Zach LaVine, G Alex Caruso, Two Future First-Round Picks

LaVine’s contract is arguably outsized at $40 million this coming season, $43 million the following year and $46 million for the 2025-26 campaign. However, he could help the Blazers be competitive right now while they build for the future.

He could slide into their starting lineup on the wing while Anfernee Simons and rookie Scoot Henderson handle backcourt duties. When Portland wants to go with a bigger lineup and Simons is resting, LaVine can scale down to the off-guard position.

Meanwhile, Caruso would give the Blazers an All-Defensive First Team selection off the bench. He won an NBA title with the Los Angeles Lakers three years ago, so he could also impart to the other members of the Blazers the wisdom and experience he gained that season while playing alongside LeBron James.

NBA TRADES, NEWS & RUMORS: Damian Lillard, Portland Trail Blazers, Zach LaVine & Chicago Bulls Updates

A starting lineup of Henderson, Simons, LaVine, Jerami Grant and Jusuf Nurkic should at least be in contention for a play-in tournament spot, given good health. At the same time, Portland would still have Nurkic as a potential trade chip in order to bring in one or two more players who could be a good fit.

As far as the Bulls are concerned, Lillard would be arguably their best and most impactful player since Derrick Rose, before the ACL injury that started to derail his career in 2012. He would give them a seven-time All-Star and All-NBA selection who is arguably the deadliest player in the game during crunch time.

Coby White would presumably start at the 2 spot in place of LaVine, giving the Bulls an interesting starting lineup. They could also look to move Vucevic, a player often brought up in trade rumors, in order to further shape their team into a contender.

NBA TRADES, NEWS & RUMORS: Damian Lillard, Portland Trail Blazers, Zach LaVine & Chicago Bulls Updates

If the price of LaVine and Caruso plus draft capital seems too steep for the aging Lillard, perhaps Chicago could ask for a role-playing reserve guard such as Shaedon Sharpe to complete the trade. Matisse Thybulle, a 3-and-D wing the Blazers recently acquired and gave an extension to, could take Sharpe’s place in their rotation.

Over 20 years after the departure of Michael Jordan, and with only one trip to the Eastern Conference Finals since then, it is time for the Bulls to make a bold move and stampede their way back into the NBA’s upper echelon.

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