Titans’ Jeffery Simmons, Bengals’ Trey Hendrickson Emerge as Legit Cowboys Trade Deadline Targets

Cowboys Stockpile Draft Ammo for a Move

The Dallas Cowboys have quietly positioned themselves for one of the most intriguing trade deadlines in recent memory. After sending Micah Parsons to the Philadelphia Eagles earlier this season, owner Jerry Jones walked away with two valuable first-round draft picks. Now, with the deadline approaching on Nov. 4, Jones appears ready to spend some of that capital — if the right defensive difference-maker becomes available.

Speaking at a press conference about Dallas’ practice facility hosting the East-West Shrine Bowl, Jones made it clear that his team is ready to buy if the opportunity arises.

“We have thought all along that if we see a way to improve this year with a trade at the deadline, then we’ll take advantage of it,” Jones said. “That’s what we positioned for to start this year.”

League sources told Yahoo Sports that Jones’ front office has already shown interest in adding elite defensive talent, specifically identifying Trey Hendrickson of the Cincinnati Bengals and Jeffery Simmons of the Tennessee Titans as potential targets.

Dallas’ Next Three Games Will Shape the Decision

At 2–3–1, the Cowboys are teetering between contender and pretender status. Over the next three weeks, they’ll face the Commanders, Broncos, and Cardinals — all winnable games that could push them to 5–3–1 and keep their postseason hopes alive.

If that happens, Jones and his staff could greenlight a splashy move for a veteran pass rusher or interior force to jumpstart defensive coordinator Matt Eberflus’ struggling unit.

However, if Dallas continues to falter and slides toward 3–5–1 or worse, the Cowboys could instead pivot toward a long-term rebuild and hold on to their draft assets for 2026.

George Pickens’ Future Adds Another Layer

One subplot complicating Dallas’ trade calculus is the contract situation of wide receiver George Pickens, acquired from the Pittsburgh Steelers in May. In the absence of CeeDee Lamb, Pickens has thrived as a No. 1 option, catching the eye of scouts across the league — and driving up his market value in the process.

An NFC personnel executive told Yahoo Sports that Pickens’ eventual free agency could motivate Dallas to make an aggressive move now.

“It’s going to be hard to pay Pickens what he’ll command,” the executive said. “Even if you set aside the personality risks, the Cowboys would be so top-heavy on offense. I think the Pickens negotiation starts at the Tee Higgins extension — around $115 million over four years.”

That financial reality could go one of two ways:

• If Dallas plans to extend Pickens, they may keep their draft picks to balance future salary cap costs.
• If they think Pickens is pricing himself out, the Cowboys could use him for one last playoff push — then reallocate those resources toward acquiring and extending a defensive star like Simmons or Hendrickson.

Hendrickson and Simmons Would Be Game-Changing Additions

Few defensive players around the league fit Dallas’ needs like Trey Hendrickson and Jeffery Simmons.

• Hendrickson, 30, remains one of the NFL’s most underrated edge rushers, with 40+ sacks since joining the Bengals in 2021. His contract is team-friendly, and his relentless motor would immediately fill the void left by Parsons’ departure. League insiders suggest his trade value could sit around a second-round pick, or possibly a third and fifth-round package.
• Simmons, meanwhile, is an elite interior lineman in his prime — a two-time Pro Bowler and the anchor of Tennessee’s defensive front. Though the Titans have publicly stated they view him as part of their long-term plans, insiders believe the right offer — a first-round pick plus a mid-rounder or starter — could change their stance.

For Dallas, Simmons would represent a long-term cornerstone — a force in the trenches that could define Eberflus’ defense for years to come.

Jerry Jones Balancing the Present and Future

The Cowboys’ situation mirrors many of Jones’ past crossroads: weighing the urgency of winning now against the discipline of building for the future.

Jones acknowledged that while Pickens has exceeded expectations on and off the field, the team must be smart about allocating resources.

“He’s not only doing it on the field, he’s doing it as part of the team concept,” Jones said. “We’ll weigh that. We knew full well that if things really went like we wanted, we’d need room available if we’re going to pay a second receiver at that level.”

It’s a delicate equation: Pickens’ breakout, Lamb’s impending return, and a defense that’s lost its bite. But with two first-round picks and plenty of cap flexibility, Dallas is among the few teams with the assets — and the owner bold enough — to make a blockbuster move.

If the Cowboys get hot over the next three weeks, expect Jones to pick up the phone. And if he does, Jeffery Simmons and Trey Hendrickson could be the names that turn Dallas from middling to menacing by November.

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