Grading the trade: Dallas Cowboys get a veteran linebacker before even making a pick on Day 2 of the 2026 NFL Draft

In return, the Cowboys are giving up Pick No. 152 in the fifth round. The trade leaves the Cowboys with no remaining picks in the fifth round after dealing their other two fifths to move up to draft safety Caleb Downs on Thursday.

Winters may not be the be-all, end-all for the Cowboys at linebacker, but he’s a major upgrade and a viable starter at middle linebacker. I would expect the front office to continue looking to add to the position group, though.

For more insight on Winters, I reached out to our own A to Z Sports NFL’s Wendell Ferreira, who explains the veteran’s departure from San Francisco is mostly about the lack of a long-term future in the Bay.

Ferreira: “Originally a sixth-round pick back in 2023, Dee Winters is entering the final year of his rookie deal. San Francisco initially took him mostly because of his positional versatility to play off-ball linebacker and edge defender, but he started his career mostly as a backup because the Niners had Fred Warner and Dre Greenlaw.

“When Greenlaw spent a year with the Denver Broncos, Winters became a full-time starter.

“He was decent in coverage and to close gaps, generating 43 stops, but missed 16 tackles in 2025. He had around 10% of his snaps at the edge, and in total generated 11 pressures. With Greenlaw back, though, Winters became expendable — especially because there wasn’t a clear path for him to stay in San Francisco beyond 2026.”

Grading the trade

It’s simple, really. The Cowboys got a starting-caliber player at the position they most urgently needed to address. And it cost a fifth-rounder. That’s close to nothing. Dallas has a long way to go to fix the position, and Winters shouldn’t change their draft approach much.

But he’s a solid addition and an immediate upgrade. The trade also lowers the pressure to move up in Day 2, potentially allowing the Cowboys to keep the three fourth-round picks they have as of this writing.

GRADE: B+