Caleb Wilson did not sound like a player content to blend in long before the Chicago Bulls put him on the floor.
At the NBA Draft Combine, the forward was asked over and over about the edge he brings every night, the same kind of relentless approach he flashed at UNC. Wilson said that mindset comes from borrowing a page from another Tar Heel who became a Bull.
"I always find something to make it personal, honestly. Just like Michael Jordan.
I try my best to find something to piss me off," Wilson told ESPN in May. "It’s hard for me to be friends with someone off the court and then try to be competitive on the court.
I just can’t do it.”
That attitude showed up again in Summer League, where Wilson made it clear he wanted a crack at the three players picked ahead of him. The league schedule never gave him all three matchups - the NBA set the games, and two of the players shut things down early - but Wilson still let his feelings be known after missing out on Utah’s Darryn Peterson.
"I feel like I’m different than all of them," Wilson said after he didn't get a chance to battle Utah's Darryn Peterson. "I can’t say they don’t enjoy basketball, but I enjoy basketball.
I love this sh*t. I’m going to play as much as I can, as much as my team will let me."
Now he’s getting his shot. The 2026-27 schedule dropped Thursday, and Wilson is lined up to face AJ Dybantsa, Peterson and Cameron Boozer eight times combined. The first one comes almost immediately, just four days into the regular season.
Here are the dates Caleb Wilson will almost certainly have circled on his calendar.
October 24, 2026 (Home)November 20, 2026 (Home)February 8, 2027 (Away)March 31, 2027 (Away)
The Bulls’ home opener brings Wilson face to face with No. 1 overall pick AJ Dybantsa. Those two will also meet in an NBA Cup game before squaring off twice more during the regular season, so this won’t be a one-and-done storyline.
There’s also no college history between them, which only adds to the intrigue. Dybantsa and Wilson never played each other in college, so the NBA will be their first real collision.
Peterson gets his first crack at Wilson on December 16, when the Bulls forward visits his home court. Utah is expected to push for the playoffs, so it’s not yet clear how much of the offense will run through Peterson early on. Still, he’s going to be central to what the Jazz build, and Wilson should have plenty of incentive from the opening tip.
The two already have a college meeting on the books to point back to. Early last season, Wilson led his team to an 87-74 win over Peterson with 24 points, 7 rebounds, 4 assists, and 4 steals. Peterson finished with 22 points, 3 assists, and 2 steals.
The longest wait belongs to the matchup many fans may want most: Wilson against Cameron Boozer.
They won’t meet until the spring of 2027, but their Las Vegas Summer League debut already gave everyone a taste. Wilson exploded for 35 points on 12-21 shooting, including 7-11 from three, matching the number of threes he made in college. Boozer answered with 23 points, 6 rebounds and 4 assists, and a veteran Grizzlies group escaped with a 97-96 win.
That game looked like the start of something, and their styles should make every meeting worth watching. Boozer brings the sturdy frame and polished fundamentals.
Wilson brings the burst, the length and the kind of versatility that can turn a game into a track meet. Out of all these pairings, that’s the one most likely to feel like a full-on collision.
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