Two retired legends have turned casual NFL roasts into a tradition—kicking back on a podcast and ripping into whichever team is trending for all the wrong reasons. It’s light, it’s funny, and more often than not, it’s brutally true. Rob Gronkowski and Julian Edelman have turned that into a sport of its own, skewering quarterbacks and franchises alike with the kind of honesty only ex-players can get away with. Dak Prescott took hits. Zach Wilson wasn’t spared. But this week, they went somewhere unexpected—and the jab carried more weight than laughter.

Because this time, it wasn’t just about bad numbers or fumbled plays. It was about legacy. About a team so starved for quarterback success that it’s become a punchline—Da Bears. And strangely, what sparked it all… was the Pope. Not just any Pope either—the first American-born one, who just happens to be from Chicago. That detail lit the fuse for Edelman and Gronk’s latest viral moment. What followed wasn’t just a joke—Gronk and Edelman delivered a roast packed with uncomfortable truth. Julian Edelman lobbed the first barb, “They got a Pope before they got a 4,000 yard passer, huh?” Gronk replied, “They sure did.”

That jab set off a chain of zingers in the reel, with Jules adding, “It’s gonna literally take a Pope to make the Chicago Bears pretty good now,” while Gronk replied, “They’re not gonna make the Super Bowl, but they’re gonna make the playoffs.” He ended the bit with mock optimism: “The Bears might be playoff decency because of the Pope.” But underneath the comedy lies a serious truth — no quarterback in the franchise’s 100+ year history has reached 4,000 passing yards in a single season.

And the struggles aren’t just historical. Even in today’s pass-happy NFL, the Bears remain the lone franchise without a single 4,000-yard season from one of their quarterbacks. Every other team has produced at least one. Chicago’s all-time passing yardage sits at 238,360—yet not a single individual campaign has crossed the 4K mark. Former Bears QB Erik Kramer put it bluntly: “You think about all the first-round draft-pick quarterbacks they’ve had since then, it really doesn’t make sense to me.”

With yet another No. 1 pick under center, the question isn’t just whether Caleb Williams can break that 4K curse — it’s whether he can redefine what Chicago football looks like.

Is Caleb Williams built to break the curse?

Recent history hasn’t been much kinder. The 2023 Bears finished 7–10, ranked 27th in passing, and moved on from Justin Fields. But the front office didn’t sit still. In the 2024 season, they brought in new offensive weapons: veteran WR Keenan Allen, RB D’Andre Swift, TE Gerald Everett, and drafted WR Rome Odunze—all to support one man. Caleb Williams, the No. 1 overall pick and 2022 Heisman Trophy winner, is the centerpiece of that rebuild. At Oklahoma and USC, he posted 8,688 total yards and 93 TDs, often drawing comparisons to Patrick Mahomes for his mobility and deep-ball instincts.

Caleb Williams played all 17 games in his rookie NFL season, threw for 3,541 yards and 20 touchdowns, but also took a league-high 68 sacks. Joe Burrow led the league with 4,918 passing yards, followed by Jared Goff (4,629) and Baker Mayfield (4,500). That gap underscores why Chicago’s passing game has been a chronic weak spot, piling pressure on every new arm that takes the helm.  And now the pressure is on.

NFL analyst Ross Tucker voiced his concerns publicly, saying Caleb Williams’ decision-making and the dysfunction around him could be red flags. A new book even revealed that Caleb’s father tried to steer him away from Chicago pre-draft, fearing it would derail his development. Inside the locker room, though, the mood is different.

Cornerback Kyler Gordon told ESPN, “He’s very poised,” noting Williams has been aggressive in testing the Bears’ defense in practice. WR DJ Moore added, “He’s been bossy lately, telling us to get the details right. He’s not afraid to speak up. That’s him being a leader.” For a rookie to command that level of respect? That says something.

So maybe Gronk’s line about needing divine help wasn’t just a joke—it was a challenge. And if anyone’s going to answer it, it’s the 23-year-old from D.C. with the arm, the swagger, and the city of Chicago on his shoulders.