Caleb Wilson wasted no time winning over Chicago Bulls fans.

On draft night, the No. 4 overall pick sported a silver rose pin on his suit. When asked whether it held any sentimental meaning, Wilson said it was to honor one of the most famous players in franchise history.

“The pin is DRose. You know, that rose who grew from the concrete. I thought it would be cool. I wanted to be a Bull, so I had it on me as a symbol of good luck," Wilson explained in June.

It was quite a clever and classy homage by the rookie. It was also only a matter of time before Wilson would shake hands with that very Bulls legend. The team shared footage of the two meeting later in the offseason. Rose has since been spotted courtside at the United Center, where many expect him to be several times this season.

Rose has even said that he sees a lot of himself in the Bulls' newest young building block. And that might be enough to get even the most pessimistic Bulls fan to perk up.

Nevertheless, Wilson is learning that reaching the high highs that Rose once did is far from easy. His team is off to a rancid 1-7 start to the season. While Wilson has still put together plenty of strong nights, the rookie also let the early losses get to him on Wednesday night. Facing off at Madison Square Garden for the first time, Wilson posted a mere 5 points against the reigning champs before Tiago Splitter benched him midway through the third quarter.

The moment will serve as a valuable learning experience. It's an incredibly long season, and Wilson is only eight games into his NBA career. Rose even stressed a similar point when he was recently asked what advice he'd give Wilson, making clear that the sample size needs to grow.

Derrick Rose Shares Advice for Caleb Wilson

In a recent conversation with Natalie Spala of NBC Chicago, Derrick Rose was asked what he might tell Caleb Wilson amid the team's ugly start to 2026-27.

“Wait until after 25 games. Every pro knows, every OG that you’ll be around, there probably aren’t that many OGs in the league right now, but they will tell you that you can’t assess your team until after 25 games," Rose said. "So, after those 25 games, you go back to the board, and you figure out how can you attack the game and work on your flaws because every rookie has flaws, and that’s the only thing that you can do.”

In other words, it sure sounds like Rose is telling the youngster to give himself some grace. Wilson is still 17 games away from that threshold, which means well over another month of NBA action. Not only will the schedule ease up a lot over that stretch, but Wilson will have a far better feel for how this group can play together and how teams are guarding him.

Heck, even a full 25 games is still a somewhat small sample size, which Rose even goes on to imply. Reaching that point isn't about knowing what to expect moving forward, but rather knowing what you need to work on to grow and better put your team in a position to win.

Patience is a virtue, especially amid a rebuilding year like this. Wilson is learning that the hard way, but at least he has plenty of mentors waiting to guide him through it. And hey, it sure doesn't hurt that one of those is the youngest MVP in NBA history!