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Hypothetical trades for the Dallas Cowboys, including a way to right a past wrong

Cowboys have a few trade assets and should use them to help bolster their roster.

Dallas Cowboys v New Orleans Saints Photo by Jonathan Bachman/Getty Images

If the Dallas Cowboys aren’t working the phones already to try to facilitate a trade or two leading up to the date (Tuesday, August 31) all 32 teams have to reduce their rosters to get under the league mandated 53-man limit, they should be. The way their current roster is constructed right now it is far from complete and they can definitely use a little bit more help at certain positions.

With that in mind, we will explore a few hypothetical trades the Cowboys could make in order to upgrade their roster prior to the start of the 2021 season. Whether it involves a few expendable players or future draft capital, the Cowboys do have some ammunition at their disposal to make them active on the trade market. But, that doesn’t necessarily mean they will be.


NFL: JAN 19 AFC Championship - Titans at Chiefs must nine he get off earlier some ofPhoto by Scott Winters/Icon Sportswire via Getty Images

LB Jaylon Smith for Kansas City Chiefs CB Charvarius Ward

The Cowboys made it pretty clear Jaylon Smith’s days as a starter were over when they signed Keanu Neal and drafted both Micah Parsons and Jabril Cox this offseason. At best he’s now forth on the depth chart, but even that’s not a given because Cox is currently nipping at his heels. That makes him a rather expensive and overpaid backup, but that could be rectified if traded.

The only way the Cowboys can recoup some of their money this year and beyond is to trade him away to a LB needy team. He’s owed $7.2 million, $9.2 million, $11 million, $11 million, and $2.4 million of the next five years, but nothing’s guaranteed after 2021. For Dallas, there’d be $6.8 million in dead money in 2022, meaning they’d save this year’s base salary ($7.2 million) and add $2.4 million of salary-cap space next season after a trade.

Kansas City has shown in the past they like former Cowboys LBs (Damien Wilson, Anthony Hitchens) and Jaylon Smith definitely fits one of their current needs. A player-for-player swap for Charvarius Ward makes a lot of sense for both teams. With L’Jarius Sneed, Rashad Fenton, and Mike Hughes already in place, Ward - who’s playing under a second-round tender - could be expendable.

Chavarius would get to return to where his professional career started, and never should’ve ended, as an undrafted free agent with the Cowboys and Smith would receive a fresh start to try to resurrect his career with a Super Bowl winning team. Dallas would be getting a 25-year-old CB with 31 career starts under his belt and KC would be getting a 26-year-old former Pro Bowl LB to fill a “need” at an important defensive position for them.


Detroit Lions v Jacksonville Jaguars Photo by James Gilbert/Getty Images

LB Jaylon Smith & CB Anthony Brown for Jacksonville Jaguars C.J. Henderson

What do you think about a two for one trade where the Cowboys send LB Jaylon Smith and CB Anthony Brown to the Jacksonville Jaguars for CB C.J. Henderson, the ninth overall pick last year? Normally, I’d probably be against dumping two veterans like Smith and Brown because they do provide value, but as things stand right now they are probably both expendable.

As mentioned earlier, Dallas can recoup some of Smith’s money by trading him away and can do the same with Anthony Brown as well. If Brown is moved via trade there’s just $1.5 million in dead money this year and the same in 2022. But, the Cowboys would rid themselves of $4.25 million and $5 million both this year and the next. Plus, Maurice Canady and Jourdan Lewis are more than capable of stepping in for him.

This is another trade that makes some sense for both teams involved. The Jaguars currently lead the league in salary-cap space, meaning they have more than enough money to add both Smith and Brown without any problems. Brown would give them a versatile inside/out corner to help stabilize the position and Smith would give them another starting caliber LB to hopefully upgrade and add depth to the position.

On the flipside, the Cowboys would be getting a former first-round pick with starting experience and tremendous upside. He could immediately step in and start opposite Trevon Diggs and give both Kelvin Joseph and Nahshon Wright a much-needed redshirt year to further develop their skill set. This trade could very well be a win-win for both organizations.


New England Patriots v Philadelphia Eagles Photo by Mitchell Leff/Getty Images

Mid to late-round pick for New England Patriots IOL Ted Karras

Without Joe Looney to fill the void as the backup guard and center, the Dallas Cowboys seem to be putting all of their eggs in one basket with Tyler Biadasz in 2021. The Connor Williams experiment to make him the backup center hasn’t gone as well as expected, leaving the Cowboys without a clear-cut solution on the roster. As things stand right now, they’d be in some serious trouble if Biadasz has to miss any length of time.

With that in mind, the Cowboys should explore acquiring someone who cannot only push Biadasz for the starting job, but also step in at moments notice as the starter when/if needed. That player could be New England Patriots OG/C Ted Karras, who is currently playing under a one-year, $3 million contract. The 28-year-old and five-year veteran has started 36 games in his career, which would add some much-needed experience to the position.

Although Karras is expected to be the backup OG/C with the Patriots this year, an offer of a mid to late-round pick for a backup player under a one-year contract could be enticing enough not to pass up. We all know New England loves to accumulate draft picks each year and this would be a way to do just that before seeing him walk next season as a free agent without getting any draft compensation in return.

For the Cowboys, parting with a mid to late-round draft pick is more than worth it considering they’d be getting a player who’d solidify the interior of their offensive line this year. With Dak Prescott trying to bounce back from a season-ending ankle injury, protecting him should be Dallas’ top priority. Making this trade would go a long ways of accomplishing just that.


New England Patriots v Miami Dolphins Photo by Mark Brown/Getty Images

LB Jaylon Smith & a fourth-round pick for New England Patriots CB Stephon Gilmore

The Stephon Gilmore to Dallas trade talk is kind of like kicking a dead horse. If we’ve heard it once we’ve heard it 1,000 times, but it’s a hypothetical trade that just won’t die regardless of how many times it keeps coming up. Yes, Gilmore is unhappy and disgruntled in New England. And yes, the Cowboys could definitely use a player with this kind of talent and experience in their secondary.

In the past this hypothetical trade has been shot down time and time again due to the fact the Patriots are wanting a premium draft pick, probably at least a second-rounder, in exchange for Gilmore, but they could possibly be swayed to take less if Jaylon Smith was tossed into the deal. After all, if not for the Cowboys drafting him in the second-round in 2016 New England more than likely would have a few picks later.

Smith plus a fourth-round pick could put Gilmore in a Cowboys uniform in 2021. If anyone can figure out how to get the best out of the Cowboys former Pro Bowler, Bill Belichick can. Smith is a similar player to Dant’a Hightower, a bit of a throwback/old-school LB, who Belichick has gotten the most out of for years now. Because of that, New England could be the perfect landing space for him to resurrect his career.

For the Cowboys, Stephon Gilmore would immediately step in and upgrade their secondary opposite second-year CB Trevon Diggs. Gilmore may be playing under a one-year contract, but he’d be a perfect bridge player until either Kelvin Joseph or Nahshon Wright was ready to take over. Plus, letting him walk after the 2021 season as a free agent could net a compensatory pick in the 2022 NFL Draft. So, there’s a chance they could actually recoup the fourth-round pick they’d send to acquire Gilmore in the first place.


Detroit Lions v Denver Broncos Photo by Justin Edmonds/Getty Images

Send a second-round pick to the Denver Broncos for EDGE Von Miller

The Cowboys aren’t known as a team who trade away premium draft picks. However, if they truly want to upgrade their defense in 2021 sending one to the Denver Broncos for Von Miller could sway them to do so. While any of the aforementioned corners already discussed would upgrade their secondary, Miller’s addition would boost the entire defense. And surprisingly enough, the Broncos may be willing to part ways with him.

As luck would have it, Von Miller is entering the final year of his contract and will count a little over $22 million against the Broncos salary cap this season. They can save $18 million by releasing him and a little more if they trade him away. Considering they already have Bradley Chubb and a couple of promising complementary pass rushers in Malik Reed and Dre’Mont Jones, Denver could try to sell Miller off to the highest bidder.

As things stand right now the Cowboys could definitely use a player of Von Miller’s talent. Yes, they do have DeMarcus Lawrence and Randy Gregory penciled in as their starters, but both come with concerns. One is coming off a recent offseason back surgery and the other has never started in an entire season in his career. Adding Miller to the mix would not only ease any concerns about those two, but give Dallas a really good trio of pass rushers.

In order to complete this trade though the Cowboys would not only likely have to part with a second-round draft pick, but also extend Miller’s contract a few years to spread out his cap hit each season. That certainly complicates facilitating such a trade, but it’s not completely undoable. He would not only help out this season, but next when Gregory becomes a free agent, making the EDGE position a “need” once again next year.

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