If you thought the Chicago Bulls’ deadline was crazy, just wait until the offseason hits!

The front office has left its options wide open as they head into the summer. The majority of the players they acquired last month are set to hit free agency, with Rob Dillingham being the only true exception. With that in mind, now that we have a small sample size to review, let’s try to predict the future for each of the organization’s newest faces. Is anyone a keeper?

Rob Dillingham

Bulls Stats: 6.4 PTS, 3.3 AST, 2.7 REB, 1.4 STL

Rob Dillingham felt destined to become a member of the Chicago Bulls once the Timberwolves rumors started. Selected No. 8 overall in the 2024 NBA Draft, the hope was that he could fill the organization’s obvious hole at the point guard position next to Anthony Edwards. Alas, the Kentucky star proved to be far too raw, making him an obvious change-of-scenery candidate as the organization prioritized a championship pursuit.

The Bulls have seemingly made development the priority moving forward, which makes Dillingham a worthwhile gamble. He still offers a mix of speed and ball-handling that few guards can mimic, and it’s still hard not to think about his extremely efficient shotmaking ability at the NCAA level. Still only 21 years old, the Bulls would be wise to keep him around and evaluate his fit alongside or in relief of Josh Giddey.

Could they look to repackage him in a bigger trade for a star-level piece? Potentially. But Dillingham is under contract for two more seasons, and I expect him to at least remain with the franchise that long.

Prediction: Stays

Jaden Ivey

Bulls Stats: 8.2 PTS, 2.2 REB, 1.2 AST

All things considered, Jaden Ivey was initially viewed as the top get of the trade deadline for the Chicago Bulls. The guard has built up many fans since his days at Purdue, offering explosive downhill athleticism and some excellent length along the perimeter. Over his first three years in Detroit, he increasingly showed flashes of being a well-rounded threat, averaging 16.1 points and 4.4 rebounds over his first three seasons.

Nevertheless, injuries have made Ivey a wildcard. Not only did the guard suffer a devastating broken fibula in 2025, but he also underwent a knee surgery just this past offseason. To say he doesn’t look like the same athlete would be an understatement, and even he knows it.

The 24-year-old is currently sidelined due to knee soreness and is not scheduled to be re-evaluated until the end of this week. While there is hope that he can return to the floor and give the Bulls a chance to examine his fit with their core pieces, there doesn’t appear to be any guarantee. There is no question that this has now thrown a wrench into his upcoming restricted free agency. Are the Bulls really prepared to bring him back, or might they prefer to wipe their hands clean and give Rob Dillingham more run?

If one thing is for sure, Ivey’s market is likely to be minimal. While a rebuilding team with money to spend might try to throw an offer sheet at him, the Bulls can likely keep him around at a very cheap cost. Heck, could there even be a chance that he plays on the qualifying offer?

At the end of the day, while I think the Bulls will consider moving on, I still lean toward believing he sticks around on a cheap deal. The buzz initially around the Bulls’ interest in him makes it hard to believe they send him packing ASAP.

Prediction: Stays

Collin Sexton

Bulls Stats: 14.2 PTS, 3.7 AST, 1.9 REB

While Collin Sexton felt like a player who was included in the Coby White trade to make the money work, he has clocked plenty of playing time in recent weeks. The guard has clearly earned some trust from head coach Billy Donovan, and he is even fresh off scoring a season-high 22 points in the team’s victory over the Milwaukee Bucks.

There is no denying Sexton’s hustle or care-factor. He seems like a great voice to have inside the locker room, and his sparkplug scoring ability makes him a legitimately intriguing sixth man. With that said, does the 27-year-old make any sense for the Bulls long-term? If the plan is to find a future building block next to Josh Giddey, moving on from Sexton feels in the Bulls’ best interest. He is only going to further crowd the backcourt, as he’s too useful for Donovan not to play on any given night.

To be clear, I can see rumors emerging that the Bulls have an interest in re-signing Sexton. He fits the “high-character” profile this front office has repeatedly coveted in the past. With that said, keeping him around doesn’t make a lot of sense, and I also tend to believe Sexton could earn a few offers from contending teams. This could end up saving the Bulls from themselves, as I have to imagine the unrestricted free agent is eager to finally suit up for a winner.

Prediction: Goes

Anfernee Simons

Bulls Stats: 15.2 PTS, 3.0 AST. 2.8 REB

Anfernee Simons is pretty easily the most talented player the Chicago Bulls welcomed in at the trade deadline. He averaged roughly 20+ points per game over his final three seasons with the Portland Trail Blazers, establishing himself as one of the NBA’s top high-volume shooters.

Then, after being sent to the Boston Celtics in the surprise Jrue Holiday trade, Simons proceeded to embrace the Sixth Man role with open arms. He proved to be a legitimately important part of what turned out to be a far better start to 2025-26 than anyone expected.

Hitting unrestricted free agency, it’s hard to imagine he doesn’t have a slew of offers come across his desk. While the guard was once seen as a possible good-stats-bad-team player, this label was likely removed over the last handful of months. Anyone could use his shooting stroke and sneaky downhill explosiveness, which is why I also couldn’t be shocked if some reports emerge about the Bulls’ desire to re-sign him. Even more than Sexton, Simons fit next to Josh Giddey makes a lot of sense on paper due to his ability to shoot on the move. You might as well consider him an even more polished and consistent Coby White.

Still, the choice will be entirely in Simons’ hands. Can I envision the Bulls overpaying to keep him around? Yes, but I ultimately think he ends up in a more competitive situation at the start of 2026-27.

Prediction: Goes

Nick Richards

Bulls Stats: 9.2 PTS, 6.9 REB, 1.1 BLK

The acquisition of Nick Richards at the trade deadline was a bit of a head-scratcher. Instead of holding onto the 22-year-old Ousmane Dieng, the Bulls chose to send him out the door in exchange for the veteran center. They may have been strapped for size, but it was an odd move for a team that didn’t seem to care much about winning the rest of the way.

Nevertheless, to Richards’ credit, he has played well in a Bulls uniform. The big man has brought some needed rim protection to the front court, and his physicality has led to roughly 3.8 free throw attempts a night (where he is shooting a solid 73.5 percent). Considering how limited the Bulls have been in the post for the last handful of years, I think there is a world where Richards does enough to earn himself a new contract with the team this summer.

I know that might have some fans rolling their eyes, but every team needs size. The Bulls also have plenty of money to spend, and Richards isn’t likely to cost a whole lot more than the minimum. None of this is to say I think they view him as their big man of the future. They don’t. But he feels like a fine option to back up whoever the Bulls bring in to act as their next building block at the position. Likewise, Jalen Smith has played great at the four this season, so I could see the team wanting to give him more run in that spot come 2026-27.

Prediction: Stays

Guerschon Yabusele

Bulls Stats: 10.3 PTS, 6.0 REB, 2.3 AST

Speaking of weird additions at the trade deadline, the Bulls surprised everyone when trading Dalen Terry for Guerschon Yabusele.

The Frenchman found his way back in the NBA after a strong run in the Paris Olympics, signing a deal with the Philadelphia 76ers ahead of the 2024-25 campaign. He played well enough in Joel Embiid’s absence to become a somewhat coveted asset this past summer, ultimately inking a deal with the New York Knicks. While Yabusele went on to appear in 41 games, he only averaged 8.9 minutes a night and really struggled to find his footing. This is ultimately why the Knicks chose to part ways with the big man.

For what it’s worth, Yabusele does seem to fit what the Bulls like in a big man. He can stretch the floor at an impressive rate, shooting 39.3 percent on 5.3 attempts a night since arriving in Chicago. The 30-year-old is also a solid passer and is never hesitant to share the ball. With that said, Yabusele is very undersized at the five (despite his bowling ball frame), which really limits his reliability. Likewise, he shockingly opted to get rid of his player option for next season to hit the open market this summer.

I believe the Bulls will look to keep one of Yabusele and Nick Richards around on a short-term deal for frontcourt depth, but my money is on that being Richards for now.

Prediction: Goes

Leonard Miller

Bulls Stats: 6.0 PTS, 2.2 REB, 1.2 AST, 0.8 BLK

Leonard Miller was stacking DNPs after arriving to the Chicago Bulls as part of the Ayo Dosunmu trade. Rob Dillingham was demanding most of the immediate attention, though the 22-year-old Miller always felt like someone who could enter the fold.

The forward offers an intimidating six-foot-ten frame with good open floor athleticism and real defensive versatility. For a team that currently lacks size and has needed a more formidable defender at the wing, Miller has the potential to carve out a real role with Chicago. In fact, he has started to do that over the last couple of games. Head coach Billy Donovan has now played him 20+ minutes in back-to-back games, and he’s rewarded him with double-digit points and 2 blocks in each outing.

At the end of the day, there is a reason Miller was viewed as one of the top high school prospects a few years back and had the chance to play for G League Ignite. The tools to be a legitimately impactful two-way wing are there, and the Bulls should be eager to give him an opportunity to showcase those tools. The Timberwolves, who were in win-now mode and had wings out the wazoo, held the youngster to just 30 games over his first two seasons.

When this offseason hits, Miller will have a club option worth a mere $2.4 million. I expect the Bulls to pick that up and give Miller a chance.