UPDATE: Joe Milton cleared waivers on Tuesday and is currently a free agent. He’s eligible to re-sign with the Cowboys via the practice squad. But he’s expected to have other offers.

The Dallas Cowboys waiving QB Joe Milton after having him make the initial 53-man roster is one of the biggest plot twists of the offseason.

The timing, especially following a preseason in which he played much better than last year, has led to many questions about the thinking behind the decision. In the aftermath of the unexpected roster cut, there are a few things we’ve learned from Cowboys insiders.

I list the three biggest pieces of intel on the Cowboys waiving Milton below.

1. Cowboys had trade conversations about Milton

This one confirms a very natural suspicion that came to mind for many Cowboys fans and media members. I speculated on an earlier article that “the most logical explanation is that Dallas tried to find a trade partner over the last 48 hours.”

My hypothesis seems to have been only partially correct. ESPN’s Todd Archer reported “the Cowboys did have some trade conversations regarding Milton before the cut down to the 53-man roster on Sunday.”

However, it seems like the Cowboys weren’t the ones initiating such conversations. That’s at least according to Bryan Broaddus of Crown Global Media.

“Did the Cowboys field calls about possibly getting their quarterbacks traded for on Sunday? Yes, that’s true,” Broaddus said on Jeff Cavaugnaugh’s YouTube show. “Did they try and trade Joe Milton before they released him? No, they did not.”

This part is particularly significant because of potential waiver interest. If the Cowboys fielded calls on potential QB trades, that likely means there’s at least one team interested in Milton. That means Milton’s chances of getting claimed on waivers are high.

2. Milton did not ask for his release

The timing of the whole thing was so odd that some speculated Milton might’ve asked for his release. There’s no truth to that story, according to Archer.

There is no truth to the story that Joe Milton asked for his release from the Cowboys, per source.

— Todd Archer (@toddarcher) August 31, 2026

What remains to be seen is if Milton does clear waivers on Tuesday (claims are due at 3 p.m. CT), does he want to retur to the Cowboys via the practice squad?

I don’t think it’s a given. But that’s a concern for later.

3. Cowboys’ interest in Milton is unclear at the moment

One more bit from Archer’s reporting that stood out: “If Milton clears waivers, he could be brought back to the practice squad, but it’s not clear whether the Cowboys would bring him back.”

It would be really weird for the Cowboys not to be interested in bringing him back to the practice squad if he clears waivers. After all, head coach Brian Schottenheimer said Monday the competition to back up Dak Prescott would continue into the season.