4. Portland's 2024 first-round pick
Acquired in the trade that sent Lauri Markkanen to the Cleveland Cavaliers, the Chicago Bulls have been anxiously awaiting the opportunity to use the first-round pick they acquired from the Portland Trail Blazers back in 2021. Unfortunately, the pick is lottery-protected through 2028, which means it won't transfer until the Trail Blazers return to being competitive.
With the way things are currently going in Portland, that may not happen any time soon. If the pick is not conveyed by 2028, it then becomes a second-round pick. For that reason, the risk attached to this pick makes it less valuable to other teams. That being said, the Trail Blazers cannot trade any future picks until their lottery-protected pick conveys, so they may still be incentivized to make a deal with the Bulls to open up their flexibility for the future.
3. DeMar DeRozan
If the Bulls were going to trade DeMar DeRozan away, the best time to do so was two years ago. There's no point in denying that fact. Off the back of an All-NBA campaign that led to a crushing first-round playoff loss, DeMar's trade value had never been higher and the Bulls were still no closer to joining the ranks of championship contenders.
That being said, DeRozan could still be worth a gamble for the right team. He may not be receiving any MVP votes this season, but DeMar is still averaging an admirable 22.3 points, 5.3 assists, and 4.1 rebounds and poses little risk on an expiring contract.
A team like the Philadelphia 76ers — who recently learned they'll be without reigning MVP Joel Embiid for the next two months — could use a player like DeRozan to help keep the team afloat in the meantime. They could easily match DeMar's salary with Marcus Morris, and a single first-round pick might just be enough to convince the Bulls to accept, rather than allow DeRozan to walk for nothing in free agency this summer.