Josh Giddey’s arrival in Chicago last offseason was supposed to be about fit and growth. He delivered on both fronts. The 22-year-old guard turned in a breakout campaign, unlocking new playmaking wrinkles and giving the Bulls a long-term piece to build around. But success on the court often leads to complications off it, and now the question is how far the Bulls are willing to go to keep him. The answer may already be hidden in how they’ve handled another young cornerstone—one whose situation reveals more about Chicago’s priorities than anything they’ve said publicly.

Because there’s another layer. Giddey is entering restricted free agency, seeking a deal in the range of $30 million annually. The Bulls, so far, have held firm at four years, $80 million. That gap hasn’t gone unnoticed, and it’s already put the team’s future direction under the microscope. And just as the contract tension was simmering, a social media post dropped that raised even bigger questions about where his head is at, and where he might fit next.

And that’s where the story took an unexpected turn. A recent Instagram post from Santa Cruz Warriors guard Taran Armstrong featured Giddey with the cryptic caption, “proceed without certainty.” Giddey chimed in the comments with a single word: “twiz.” A harmless exchange? Maybe. But the timing, right in the middle of his contract standoff, was impossible to ignore.

The comment might have looked harmless initially, but the context gave it weight. Giddey wasn’t pictured with a Bulls teammate but a Warriors guard. For a player caught in contract tension, those optics matter. Fans quickly began wondering if the post was more than just a casual link-up with a fellow Aussie; maybe a subtle nod that his eyes aren’t fixed solely on Chicago.

It also fueled whispers about Golden State’s future guard plans. With the Warriors balancing minutes between Stephen Curry and younger backcourt pieces, the idea of a long-term backcourt playmaker alongside Curry has obvious appeal. Giddey, still just 22, fits that mold perfectly. One cryptic Instagram post won’t spark a trade, but it was enough to stir curiosity when his relationship with the Bulls is far from settled.

Coby White’s Security Signals the Bulls’ Priorities

If there was any doubt about Chicago’s stance, the contrast with Coby White makes it clear. As an insider noted, “I know multiple teams tried to trade for Coby this summer… There was some chatter that he was almost traded on draft night. The Bulls love him, though. He’s not going anywhere. They have shot down trade inquiries for him.” Their willingness to line up an $89 million extension over four years underscores their faith in White as a long-term cornerstone.

However, Chicago Bulls reporter Joe Cowley of the Chicago Sun-Times expects Coby White to test the market next summer rather than settle early.

“White is eligible to sign a four-year, $89 million extension in July but would be much better served to bet on himself and get a much bigger payday as an unrestricted free agent after next season,” Cowley wrote. “That payday could make him a $40 million-per-year player.”

If White continues his upward trajectory, it sets up a massive gamble—one that could reshape both his career earnings and the Bulls’ long-term financial planning.

That decision speaks volumes about their priorities. White’s great shooting year and improved decision-making have given the front office confidence that he can be the stabilizer in the backcourt. Giddey’s ceiling may be higher, but Chicago has been reluctant to budge beyond its $80 million line for him, even as the guard’s camp pushes for a richer deal.

Although Coby White is currently on a bargain three-year, $36 million deal he signed back in 2023, the Bulls don’t intend to move him anytime soon. Since he can’t extend at true market value until 2026, Chicago’s plan is clear — hold on to him and use his Bird rights to secure a new contract next summer rather than risk losing him via trade.

It’s a strong sign of long-term commitment, especially given White’s rise as one of the team’s cornerstones.

The result is a roster crossroads. Locking in White while lowballing Giddey risks creating tension inside the locker room, particularly when the two guards have been billed as a potential backcourt of the future. For now, the Bulls appear committed to betting big on White, even if it means leaving Josh Giddey’s future unsettled.