The hats were loud, the bourbon louder. But when Aaron Rodgers appeared in the paddock at Churchill Downs, Steelers fans didn’t cheer—they seethed. One post summed it up best: “If you’ve got time for mint juleps, you’ve got time to sign a damn contract.” Pittsburgh had been patiently—now impatiently—waiting for clarity. Was their next quarterback dancing with the derby or dodging commitment? The answer, apparently, depends on what phase of the NFL offseason you ask about.

When Steelers fans noticed Aaron Rodgers at the Kentucky Derby, their reaction wasn’t joy — it was frustration. It’s not hard to see why. The four-time MVP has been taking his time deciding whether he’ll wear black and gold in 2025. While Mike Tomlin and the Steelers seem quietly confident about landing Rodgers, the 41-year-old QB has kept things vague.

According to former NFL quarterback and current ESPN analyst Matt Hasselbeck, though, the clock is ticking. During a recent appearance on The Herd with Colin Cowherd, Hasselbeck discussed Rodgers’ status. Having once walked the same offseason tightrope, Hasselbeck offered insight into what really matters for veteran QBs during spring training.

“For a veteran quarterback, phase one feels like a waste of your time,” he said, referring to the NFL offseason’s early stages. “It’s just lifting. I could lift with my guy where I like to lift.” He went on to say that phase two, where veterans “throw to guys on air”, isn’t much better. Then came the moment of truth. “Phase three, I think, is really important. So, for the Pittsburgh Steelers, I believe that’s May 27th.”

That’s when 11-on-11 drills begin — a marker Hasselbeck believes is when Aaron Rodgers could finally make his move. With Rodgers still unsigned after the draft, and no rush on either side, the May 27 date suddenly feels like a deadline circled in red in the Steelers’ front office.

Mike Tomlin’s roster moves may influence Aaron Rodgers’ decision

There’s more fuel to the speculation fire. Pittsburgh passed on drafting Shedeur Sanders and left the fourth quarterback slot open — a clear sign they’re reserving it for someone with Rodgers’ profile. But in doing so, Mike Tomlin may be preparing to part ways with one of his current stars: wide receiver George Pickens.

NFL Network insider James Palmer reported that the relationship between Pickens and the Steelers “has not gone well behind the scenes.” In Palmer’s words: “Could he play for them in 2025? Certainly. Would he be departing after the season? Yes. In a lot of people’s minds.”

The wideout is entering the final year of his rookie deal — a four-year, $6.75 million contract — and has already voiced his desire for a raise. Statistically, his case is solid: 174 receptions on 293 targets, 2,841 receiving yards, and 12 touchdowns across three seasons. Yet the Steelers reportedly explored trading him before the 2025 draft. According to Dianna Russini, teams like the Cowboys had a serious interest.

Keeping Pickens around means providing Rodgers with a potent weapon that would match his desire of wanting to play for a serious Super Bowl contender. Even at the cost of letting him walk away for nothing next year. Whether the trade move was due to DK Metcalf’s arrival or a larger roster reshuffle, one thing is clear: Pittsburgh’s waiting game with Aaron Rodgers might be forcing moves elsewhere.

Will Rodgers finally sign? Will Pickens walk? All eyes are now on May 27 — and on Rodgers to decide if he’s ready to ride with the Steelers.