Reexamining the Bulls' four-guard logjam with free agency decisions looming

Things look different now for Simons, Ivey, Sexton and Dillingham.
Feb 7, 2026; Chicago, Illinois, USA; Chicago Bulls guard Jaden Ivey (31) guard Anfernee Simons (22) guard Collin Sexton (2) center Nick Richards (13) and forward Isaac Okoro (35) on the court during the second half against the Denver Nuggets. All five players weren’t 0n the team at the start of the season at United Center. Mandatory Credit: David Banks-Imagn Images
Feb 7, 2026; Chicago, Illinois, USA; Chicago Bulls guard Jaden Ivey (31) guard Anfernee Simons (22) guard Collin Sexton (2) center Nick Richards (13) and forward Isaac Okoro (35) on the court during the second half against the Denver Nuggets. All five players weren’t 0n the team at the start of the season at United Center. Mandatory Credit: David Banks-Imagn Images | David Banks-Imagn Images

Bulls Executive VP of Basketball Operations Arturas Karnisovas transformed his team’s roster at this year’s trade deadline, swapping a trio of franchise stalwarts for a glut of guards and a couple of so-so big men.

A month later, it’s time to reassess those moves and ask the million-dollar question: Which of those guards will be in Chicago next season?

Coby White, Ayo Dosunmu and Nikola Vucevic exited the Windy City for greener pastures in Charlotte, Minnesota and Boston, respectively. In their stead, the Bulls landed a quartet of guards in Jaden Ivey, Rob Dillingham, Collin Sexton and Anfernee Simons. 

Dillingham is still on his rookie deal, but Sexton and Simons will be unrestricted free agents this summer, and Ivey will be a restricted free agent.

Here’s a rundown of how each of those guards is performing and whether they’re more likely to stay or go this offseason.

And just for fun, we'll bring in the good ol' Magic 8 Ball for advice, because what human really knows what Karnisovas has planned? Does he even know?

Injuries and inconsistency are helping sort out the Bulls' guard problem

Each member of this foursome has had his ups and downs.

Collin Sexton

  • 2025-26 stats with Chicago: 11 games, three starts, 25.4 minutes per game, 15.1 points per game, 2.2 rebounds per game, 2.0 assists per game, 1.5 steals per game, 47/33/82 shooting splits

Sexton has been as steady and slightly above-average as advertised.

At 27 years old, he's maxed out as a rotation guard who's capable of getting hot and swinging a game now and then, as evidenced by his 30-point, five-assist, two-steal performance in Chicago's 105-103 win over the Phoenix Suns on March 5.

The Magic 8 Ball's prediction: Outlook not so good.

Anfernee Simons

  • 2025-26 stats with Chicago: six games, five starts, 28.3 minutes per game, 15.2 ppg, 2.8 rpg, 3.0 apg, 44/32/100 shooting splits

Simons was the centerpiece of the Vucevic trade from the Bulls' perspective (are we sure about that, though?). The 26-year-old is a talented scorer who's averaged more than 20 points per game in multiple seasons and is an efficient, high-volume 3-point shooter.

He hasn't played since Feb. 21, though, and would be a better fit as a sixth or seventh man on a contending team.

Magic 8 Ball's prediction: Don't count on it.

Jaden Ivey

  • 2025-26 stats with Chicago: four games, three starts, 28.8 mpg, 11.5 ppg, 4.8 rpg, 4.0 apg, 2.0 spg, 42/38/89 shooting splits

Ivey was arguably the most interesting acquisition Karnisovas made at the deadline.

He was surging during the 2024-25 season before breaking his fibula. He hasn't been the same player since, and has been out of the Bulls' lineup since Feb. 11 as he deals with knee soreness in his other leg.

Ivey will be a restricted free agent this summer, is still only 24 years old and still carries a lot of potential.

Magic 8 Ball's prediction: Signs point to yes.

Rob Dillingham

  • 2025-26 stats with Chicago: 11 games, zero starts, 19.3 mpg, 6.8 ppg, 2.8 rpg, 3.3 apg, 1.2 spg, 38/17/79 shooting splits

Dillingham has the highest upside of any player the Bulls acquired at the deadline. The 21-year-old was the No. 8 pick in the 2024 draft after a one-and-done season at Kentucky, where he averaged 15.2 points on 44.4 percent shooting from three (4.4 attempts per game) in 23.3 minutes.

His enticing skill set as a three-level scorer with an elite first step remains. It's up to the Bulls to unlock it.

His rookie contract runs through the 2027-28 season.

Magic 8 Ball's prediction: It is certain.

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