Grade the trade: Bulls land Damian Lillard in shocking proposal

Chicago Bulls, Damian Lillard. Mandatory Credit: Trevor Ruszkowski-USA TODAY Sports
Chicago Bulls, Damian Lillard. Mandatory Credit: Trevor Ruszkowski-USA TODAY Sports /
1 of 3

The Chicago Bulls are at a crossroads after missing the playoffs in five of the last six years. DeMar DeRozan is entering the final year of his contract, Lonzo Ball is already out of the season, and the team just re-signed Nikola Vucevic. They need to pick a direction and go towards it. The Bulls want to contend, but their disastrous 2023 leaves questions about their ability. Do they need an upgrade to make that a reality?

The Bulls have three All-Stars still clinging to their prime and a deep roster around them. They do not have a top 20 player and the fit is questionable. Chicago lost in the first round of the playoffs in 2022 and nearly knocked out the Heat in the Play-In Tournament last season. Instead, Miami advanced and made a run to the NBA Finals.

The only upgrade the Bulls should consider is adding a superstar. Damian Lillard is the best player on the market right now, and there have been rumblings, but it will take a massive offer for Chicago to get involved.

Can the Chicago Bulls trade for Damian Lillard?

The Bulls have shown interest in Damian Lillard, but their assets are limited.  They have Portland’s pick in 2024 but owe San Antonio a protected first in 2025. The Bulls can only trade two first-rounders and three seconds when looking to pull off a blockbuster deal.

The Trail Blazers want to get a third team involved in the Lillard sweepstakes, which could help Chicago. If Portland gets assets from the other team, Chicago has to offer less to make a deal. The Suns are rumored to be the franchise with Deandre Ayton heading to Rip City.

The Chicago Bulls can and will make an offer for Damian Lillard, but will it be the winner? That will depend on what others are willing to give up, but the latest proposal has the three sides working out a deal.