5 Early Bulls Games That Will Define The Caleb Wilson Era

The Chicago Bulls' early 2026-27 matchups promise thrilling tests of skill and strategy as they face off against formidable opponents, making these games a must-watch for basketball fans.

The 2026-27 Chicago Bulls schedule dropped Thursday, and the early stretch already gives fans a handful of games worth circling.

These aren’t just dates on a calendar. They’re the first real checkpoints for a Bulls team trying to show what it is, what it can defend, and how quickly its new pieces can mesh. From a defending champion to a pair of East opponents with real credibility, the opening month is loaded with useful tape.

The most obvious headliners are the two meetings with the New York Knicks, set for Oct. 28 and Nov. 4.

That’s a fast double dose of the defending champions, and it should tell a lot about where Chicago stands right away. The Knicks bring the kind of all-around strength and postseason dominance that can expose weaknesses in a hurry.

If the Bulls find any pockets of success in either game, that will matter. So will the coaching staff’s ability to make adjustments from one matchup to the next in such a short span.

There’s also plenty of intrigue in how Caleb Wilson and Matas Buzelis fit together against that kind of opponent.

Another early measuring stick comes Nov. 11 against the San Antonio Spurs. That one stands out because of the Spurs’ talent on both ends and because it should put a spotlight on a problem Chicago dealt with last season: protecting the paint.

The Bulls added Wilson and, especially, Nic Claxton, and this game should offer a clear look at how much that helps. Offensively, it will also be a strong test for Wilson against a defense like San Antonio’s.

Two days later, on Nov. 13, the Bulls get the Atlanta Hawks in what looks like one of the more realistic barometers of the group’s progress. Both teams have young talent.

Both have lived in the play-in lane. And Atlanta comes in with a more accomplished recent résumé, including a 2025-26 season that ended with the sixth seed and two wins over the Knicks.

If Chicago can match that level early, or push past it, that would say plenty about the direction of the roster.

The other game that belongs on the list is Nov. 2 against the Philadelphia 76ers. Philadelphia’s starting lineup got a major jolt with the additions of LeBron James and Jaylen Brown, giving that group an outrageous amount of individual talent even if the fit is fair to question.

For the Bulls, the defensive assignment is the story here. Tyrese Maxey, Joel Embiid, Brown and James all on the floor at once would be a brutal test, and that’s exactly why this one matters.

There’s also an obvious honorable mention in the opener on Oct. 21 against the Toronto Raptors. It’s the first game of the regular season, so it almost makes the cut by default, but it still carries real weight.

Fans will get their first look at Wilson in a Bulls uniform in a regular-season setting, and it will be Tiago Splitter’s first game at the helm. After the hope that Wilson’s arrival has brought back, this one is hard to miss.

In Other News...

Bulls Schedule Puts Early Pressure On A Rebuild Already Under Scrutiny

The NBAs release of the 2026-27 schedule gives the Bulls their first real road map for a season that already figures to be watched closely in Chicago. They open with two road games before coming home for a matchup with the Washington Wizards, and the league has also handed them three nationally televised games, a small but meaningful sign that the Bulls will remain under a brighter spotlight than some of their peers during the first months of the rebuild.

Beyond the marquee dates, the slate lays out the kind of grind that can shape how a young roster is judged: back-to-backs, extended road trips, the NBA Cup group stage and a handful of noted return dates for players who will draw extra attention whenever the Bulls see them. For a team trying to establish direction while answering questions about the rebuild, the schedule does not offer much breathing room, and Chicago will find out quickly whether its reset can hold up against the travel and the scrutiny. [Read more 🡒]

Bulls Keep Reshaping Their Staff Around A Very Clear Future

The Bulls continue to put their stamp on the organization before the 2026-27 season, this time adding Jordan Brink as an assistant coach and director of player development. Brink arrives with a background that includes stops with the Knicks and Pistons, and his rsum fits the kind of dual-purpose hire Chicago has been making as it reshapes both its bench and its developmental pipeline.

Bryson Graham and Tiago Splitter have been steering a broader staff overhaul, and Brinks arrival is another sign that the Bulls are building with a clear long view in mind. For a team trying to align its front office, coaching staff and player development infrastructure, these hires matter because they point to a unified plan rather than isolated moves. [Read more 🡒]

Bulls Suddenly Have A Real Chance At A Young Backcourt Upgrade

Bennedict Mathurins future has become one of the more interesting offseason plots for a Bulls team that is still looking for ways to add young talent to the backcourt. The restricted free agent was acquired by the Los Angeles Clippers, but he has not gotten a clear signal that a new contract offer is coming, and the Clippers recent decision to re-sign Bradley Beal only adds another layer to the uncertainty around where Mathurin fits.

For Chicago, the appeal is obvious. The Bulls have been searching for a way to upgrade their guard rotation with a player who still has room to grow, and Mathurin checks that box if the market opens up the right way. There have been exploratory conversations between the two sides, and the structure of a deal would tell a lot about how aggressively Chicago wants to pursue the upside here. For now, it is enough to say the Bulls have positioned themselves in a conversation that could matter more as the rest of free agency settles in. [Read more 🡒]