The Chicago Bulls have plenty to think about this offseason, especially after a disappointing season where they were unable to make it to the playoffs. Various reports have come out that the Bulls are expecting to retool their roster around Zach LaVine, and this has understandably caused an avalanche of rumors surrounding the team’s roster going into next season.
One of the leading narratives is that DeMar DeRozan may be traded this summer as a way to make the Bulls younger and shift the franchise’s direction. The Chicago Bulls have an opportunity to make some big moves with DeRozan, as he has recently had some of the best years of his career. This should keep his trade value high, despite the fact that he will be 34 years old at the beginning of next season.
The Chicago Bulls have high-quality trade pieces that could lead them to make potential blockbuster moves this offseason.
On Wednesday, DraftKings released a mock trade that sends DeMar DeRozan to the Portland Trail Blazers in exchange for a few key pieces that could fit the Bulls’ needs.
This blockbuster trade would send two of the Chicago Bulls’ best players to Portland while the Trail Blazers would give up their starting center of seven years, a prolific scorer, and a highly coveted draft pick.
The Trail Blazers were one of the three big lottery winners on Tuesday, outperforming their odds and getting the 3rd overall pick in the draft. They came in with the 5th best chance of winning the lottery, and a 10.6% chance of getting the pick they eventually received. They were able to strike gold and move into the top 3, which is huge as this upcoming draft is mainly thought of as being similar to the 2020 draft, with the top three prospects massively differentiating themselves from the rest of the pool. The Chicago Bulls saw this firsthand, as they received the fourth pick in the draft and missed out on Anthony Edwards, James Wiseman, and LaMelo Ball.
The Blazers have expressed interest in trading this pick, as they could use it to bring another star to Portland and receive a star to pair with Damian Lillard, who judging by recent comments, may be getting fed up with the direction of the franchise. This is part of the reason why this mock trade has been proposed, which I will evaluate from both sides.

Portland is currently under tremendous pressure from their superstar Damian Lillard. The 32-year-old has played all 11 seasons of his career with the Trail Blazers and has been one of the best in the franchise’s history. He faced injuries in the 2021-22 season, but came back this year and dominated in 58 games.
Lillard averaged 32.2 points and 7.3 assists per game, which were 3rd and 13th in the league, respectively. He delivered some outstanding performances, including a 71-point game against the Houston Rockets, showing that he has not lost a step since his injury.
Damian Lillard is forcing the Trail Blazers’ hand to bring another star to Portland.
Lillard has shown his commitment to stay in Portland, but is growing tense as the team has never really provided him with another star to make a championship run. This trade would give Portland two huge pieces to convince Lillard to stay with the Blazers, as they are getting another dominant scorer and one of the best defenders in the NBA.
This is a good trade for the Trail Blazers and it would show they are committed to winning now, as they would be trading their best young player in Anfernee Simons and a top-tier draft pick, but getting two pieces that, paired with Lillard, could attempt to make a run at a championship.
It is definitely tough to consider for Portland, as they could potentially be mortgaging their future for one guaranteed year of DeMar DeRozan and two for Alex Caruso. The key decision for Portland is between trading Lillard or the 3rd pick, as keeping both is a very unlikely scenario. With this trade, the Trail Blazers starting lineup would be the following:
- PG: Damian Lillard
- SG: Alex Caruso
- SF: DeMar DeRozan
- PF: Jerami Grant
- C: Drew Eubanks
Assuming that the Trail Blazers can resign Grant and Eubanks, who are both free agents this offseason, they will have this starting lineup with Shaedon Sharpe, an excellent young player, as the 6th man. This would be an upgrade for the Blazers, as they would add some much-needed perimeter defense with Caruso while bringing a much better 2nd scoring option in DeMar DeRozan. A big three of Lillard, DeRozan, and Jerami Grant would give the Blazers a chance to make the playoffs again, assuming everyone stays healthy.

In this trade, the Chicago Bulls would be giving up two of their best players, but could receive a haul in the long-term. In this trade, the Bulls have a chance to get two excellent young pieces as well as a solid center. Looking into the best-guaranteed piece, Anfernee Simons has shown tremendous potential and development during his first five years in the league.
Simons is an electric scorer and averaged 21.1 points per game this season on 44.7/37.7/89.4 shooting splits. He is a really good three-point shooter, making 38.9% of his attempts over the last two seasons while averaging 8.4 three-point attempts per game, more than any player on the Bulls this season.
The addition of Anfernee Simons and Jusuf Nurkic could add much-needed shooting and rim protection to the Bulls.
The shooting that Simons brings to the table is huge for the Bulls, as Chicago struggled mightily from three this year, making just 10.4 threes per game which was the worst mark for any team in the NBA. Simons as a three-point shooter could really elevate the offense and bring it to the next level, as teams will have to respect another player’s abilities on the perimeter. Additionally, he has been able to penetrate well, scoring the ball well in the paint.
https://twitter.com/B2BFR/status/1599390849275609088
Simons scored a career-high 45 points in this game against the Jazz, where he shot 15-for-25 from the field and 7-for-12 from deep. Simons has an unreal scoring ability at just 23 years old and is an underrated playmaker, averaging 4.1 assists this season. As a shooting guard, he will be a welcome addition to the team as he can liven up the offense.
His main weakness is his defense, however. He has been a below-average defender in his short time in the league, often contributing less effort on that side of the ball and getting caught watching. However, Simons has the athleticism to be an average defender in this league, he just needs to lock in and focus defensively, which will come as he develops. If the Bulls can help him gain focus on that side of the ball, Simons can be a solid defender and a potential all-NBA player.
This trade would also give the Bulls Jusuf Nurkic, the Blazers’ 28-year-old starting center. After Nurkic’s freak injury in 2019, he has slowly come back and adjusted his game. He has attempted 205 threes in the 145 games he has played since coming back (34% shooting), which is a stark contrast from the 52 he attempted in his first 318 contests. His strengths lie in the pick-and-roll, where he uses his 6’11”, 290-pound frame to set strong screens that get his shooters open.
Additionally, he is a strong rebounder, averaging 9.8 rebounds over the last three seasons (2.5 of which are on the offensive glass). He has also averaged around 3 assists per game since coming back from injury, which shows that he is a solid passer as a center. Finally, Nurkic is a solid rim protector who would be a defensive upgrade from Nikola Vucevic if Vooch ends up being moved during the offseason.
One of the main concerns with Nurkic is his injury history. Over the last four seasons, he has not played 70% of his team’s games once, which is of slight concern to the Bulls especially considering the fact that Nikola Vucevic was able to play all 82 games this year. This could limit the upside potential of the Bulls’ trade, as it may not give as permanent of an answer at the center position as Chicago would have hoped.

The final piece of the trade, and potentially the most important, is that number 3 overall pick. The Chicago Bulls, if they make this trade, would likely have two options here. The three top prospects in this draft are Victor Wembanyama, Scoot Henderson, and Brandon Miller.
The consensus is that Wembanyama is going to be drafted first overall by the San Antonio Spurs, and the Bulls would likely choose the prospect that the Charlotte Hornets do not select at #2. According to current mock drafts, this would mean that the Bulls would receive Scoot Henderson, point guard for the G League Ignite.
The Hornets would likely pass on Henderson as they have a set backcourt in LaMelo Ball and Terry Rozier, but are missing a young small forward with potential, which Brandon Miller would solve.
The Chicago Bulls can get one of the best point guard prospects in recent memory with the 3rd pick.
If Scoot Henderson falls to number three, that would be the ideal scenario for the Bulls as he would give Chicago the point guard they have been searching for. Henderson has drawn comparisons to Derrick Rose and Russell Westbrook due to his explosive speed and impressive dunk and layup package.
Henderson was outstanding in the G League, averaging 16.5 points and 6.5 assists per game. He showed his ability as a playmaker as well as his impressive basketball IQ, which is significantly better than what is expected of a 19-year-old. Additionally, he has great potential on the defensive end, as he has solid instincts and tremendous athleticism that enable him to make plays. He tends to be overzealous on defense, however, as he overcommits and fouls more than he should, which will improve with time.
Seemingly the only weakness that Henderson has is his three-point shot, which he made less than 30% of the time in the G League. One encouraging note is that Scoot has an excellent midrange jumper, which gives optimism that he can still develop that deeper shot as time goes on. He is still young and just came out of high school, so the NBA distance is an adjustment that he is going to have to make. However, projections are stating that he will be a perennial all-star.
If the Bulls are able to make this trade and get Scoot Henderson, their starting lineup would definitely be something interesting and could have some excellent upside:
- PG: Scoot Henderson
- SG: Anfernee Simons
- SF: Zach LaVine
- PF: Patrick Williams
- C: Jusuf Nurkic
This would be a solid starting lineup with tons of potential, as it features three players below the age of 25 with its oldest player being Jusuf Nurkic, who will be 29 at the beginning of the season. The Bulls will also have some excellent young pieces in Coby White and Dalen Terry, the latter of which may actually be able to get more minutes and develop this year.
If the Chicago Bulls are able to make this trade, they will show that they are moving in a younger direction and have a bright future. The Bulls may be able to develop into a strong contending team before Zach LaVine’s current contract expires. This offseason, they may also need to get a power forward with size, but this trade would solve several issues that the team is currently facing. This is a potential win-win trade that can set the Bulls and the Blazers on a beneficial path. The Bulls may be giving up their best defender and a star, but it could move Chicago out of the purgatory that they are currently in.

