Well, well, well. Here we go again. Another offseason, another round of Will Jerry Actually Do It? This time, the big rumor floating around is that the Cowboys are shopping Dak Prescott. And not just to any team—but to the Browns, a franchise that has spent decades trying to find that guy under center. Sounds crazy? Maybe. But then again, this is Jerry Jones we’re talking about.

Are you actually surprised? Prescott, for his part, hasn’t exactly been thrilled since Mike McCarthy left. “Bummed, because we built some things,” he said back then. “But I guess they couldn’t reach an agreement. SMH.” If you needed any more proof that things are getting messy in Dallas, there it is.

The man has been a Cowboy for nearly a decade, and now, he’s stuck watching his name pop up in trade rumors while the front office plays financial gymnastics. His four-year, $240 million contract extension from last season? Already restructured. And now, whispers of a blockbuster deal with Cleveland are making the rounds.

So, is there any real chance of Prescott suiting up in orange and brown next season? According to Bruce Drennan, the Browns and Cowboys are negotiating as we speak. That’s huge. And the Dawg Pound wouldn’t mind a Dak after the growing pains with Deshaun Watson.

But let’s not forget the elephant in the room: money. If Dallas were to trade Prescott right now, they’d be staring at a $95.3 million dead cap hit. That’s not just bad—that’s franchise-crippling bad. However, if they wait until after June 1? They’d actually save $2 million in cap space. Small, sure, but in Jerry’s world, every dollar counts.

And here’s where things get even spicier. If Dallas is serious about moving on from Prescott, they need a Plan B. Enter the Browns’ No. 2 overall pick in the 2025 NFL Draft. If this deal happens, you know the Cowboys are eyeing their next franchise QB. Colorado’s Shedeur Sanders? Maybe. The Sanders-Jones connection isn’t exactly a secret, and there was even a moment where Deion Sanders was floated as a Dallas coaching candidate. Coincidence? Probably. But this is Jerry we’re talking about—nothing is ever just a coincidence.

All this said, a Prescott-to-Cleveland move still feels more like offseason fantasy than reality. The cap situation is ugly, and Cleveland doesn’t exactly have much wiggle room itself. But hey, stranger things have happened in the NFL.

Another strange thing for Jerry Jones’ Cowboys? Joe Milton

Yes, you read that right. The Dallas Cowboys, who already have their starting quarterback in Dak Prescott (for now), are reportedly sniffing around the idea of trading for Joe Milton. Why? Good question. With Cooper Rush heading to Baltimore in free agency, Dallas needs a backup.

And apparently, Milton’s name has surfaced as a potential option, according to 105.3 The Fan’s Bryan Broaddus. But before you start thinking this is a done deal, there’s a catch—New England doesn’t really want to trade him.

“Just hearing some whispers from various people that they’re going to maybe dip their toe in the pool here and see what they get,” Broaddus said. To put it simply: the Cowboys are poking around, but the Patriots aren’t exactly putting Milton on a discount rack. If they do move him, the asking price is likely a fifth-round pick. And that’s where things get interesting. Would Dallas part with a late-rounder in 2025? Or would they prefer to kick the can down the road with a 2026 pick?

Now, let’s talk about Milton himself. The guy had a solid Week 18 showing against the Bills’ backups, throwing for 241 yards and a touchdown. But let’s be real—that’s a tiny sample size. As Sports Illustrated’s Albert Breer put it, “I’d be pretty stunned if any team gave up a top-100 selection for him.”

And it’s not hard to see why. Milton bounced between Michigan and Tennessee in college, never quite locking down the starting job long-term. It took him until 2023 to become the full-time starter for the Volunteers. Good, but not exactly screaming future franchise QB.

Even if the Cowboys do trade for him, where does he fit? Well, this does co-align with the whole Dak Prescott to Cleveland rumor. But if we ignore that for a second, Dak is here for the time being. And let’s not forget, Dallas already took a swing on another young QB in Trey Lance last year. Are they really going to add another project to the mix? If anything, Milton would be nothing more than an insurance policy, barring an unexpected Prescott injury.

Bottom line? The Patriots may listen to offers, but they’re not desperate to move Milton. And for Dallas, this feels more like an offseason curiosity than a real plan. Unless Jerry Jones is up to something again—which, let’s be honest, is always a possibility.