Dak Prescott to Browns Trade Rumors Rekindled by Original Reporter as Joe Milton III Sends a Clear Message to Cowboys

There’s watching the circus, and then there’s being part of it. If you’re a Cowboys fan, you know what that feels like with Jerry Jones at the wheel. But even for all his wild moves, would he really wake up one day and decide, ‘You know what? Let’s send Dak Prescott to the Browns‘. That would be next-level madness… right?

Well, that depends on who you ask. Enter Bruce Drennan, who is doubling down on his original claim: “I stand by the statement I laid on you last week. This could come about.” He insists Dallas could ship Prescott to Cleveland in exchange for Greg Newsome and Pick 33. No Browns first-rounder involved. Convenient timing, considering the Cowboys just traded for Joe Milton III this morning. Coincidence? Drennan doesn’t think so.

But here’s where things get tricky—the numbers don’t add up. One fan put it bluntly: “Someone tell Bruce that the Cowboys’ restructure of Dak makes this impossible. It would literally break them cap-wise.” And he’s not wrong.

Bruce Drennan is doubling down on his claim the Browns could trade for Cowboys quarterback Dak Prescott.

“I stand by the statement I laid on you last week. This could come about.”

Drennen says he was told the trade would involve Prescott to Cleveland in exchange for Greg… pic.twitter.com/rspKc53aTo

— The Dawgs – A Cleveland Browns Podcast (@thedawgspodcast) April 3, 2025

Prescott’s cap hit for 2025 sits at $52.9 million, and it skyrockets to $76.5 million in 2026, making any trade financially unrealistic. Additionally, his no-trade clause gives him full control over whether he stays or leaves, meaning even if the Cowboys wanted to move on, Dak has the final say.

Meanwhile, the Browns are already strapped with Deshaun Watson’s massive contract, leaving them with only $18 million in cap space for next season. Unless Cleveland finds an extra $50 million lying around, this deal is dead on arrival!

So, is this real smoke or just a Drennan-induced fire? For Cleveland, the idea is at least worth entertaining. Their QB situation is a mess—Deshaun Watson’s health is uncertain, and the team isn’t exactly brimming with trust in their backups.

But would they really go all-in on Prescott when they already have $230 million tied to Watson? It’s a long shot, but desperate teams do desperate things. And the Browns are desperate to stay in the AFC North arms race.

Then there’s Dallas. Trading Dak now would mean waving the white flag on the 2025 season before it even begins. Sure, they grabbed Joe Milton, but is a rookie really their fallback plan? Prescott might not have a Super Bowl ring, but he’s still a top-10 QB. If this trade were legit, you’d expect every NFL insider to be all over it. But so far, it seems, Bruce Drennan is creating his dream fantasy line-up. Because the Big D is looking forward to a Joe and Dak under center depth.

Dak Prescott’s backup has a re-affirming message for his team

Joe Milton III will not let Dallas down. Jerry Jones has taken it down already. Now, it’s just about the feelings of those living in the ‘raised’ D. Joe has made it clear—he’s ready to work. And if that means waiting for his shot behind Dak Prescott, so be it. But make no mistake, Milton didn’t land in Dallas by accident.

“My family grew up a Cowboys fan. My mom always had a Cowboys shirt on. She always talked about them. Living in Texas has been a longtime dream of mine. And now I’m with them. I’m ready to work,” he told Jordan Schultz. Sounds like someone just walked into their dream job.

The move comes after Jerry Jones sent a fifth-round pick to the Patriots for Milton and a seventh-rounder. A small price to pay for a backup who some scouts believe has more upside than the quarterbacks in the 2025 draft class. The Cowboys needed depth after Cooper Rush signed with the Ravens, and Milton—who spent last season on New England’s practice squad—fits the bill.

The guy can sling it, and his athleticism gives him a different edge from Prescott. But let’s be real—this isn’t about 2025. This is about what happens when Prescott eventually leaves.

Right now, Prescott is still QB1. That’s not changing. But Milton has a chance to develop under Brian Schottenheimer and learn from one of the most scrutinized quarterbacks in the NFL. If things go south—injury, contract drama, or a sudden decline—Milton could be the next man up.

So, is Milton just another backup, or did Jerry Jones just stumble onto a hidden gem? Time will tell. But one thing is certain—he’s not in Dallas just to watch.

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