When the league year begins and free agency opens on March 18th, it will be the first opportunity for the Dallas Cowboys to begin retooling their roster in the image that new Head Coach Mike McCarthy and the rest of the coaching staff envision for the 2020 Cowboys. Though there is a lot of optimism surrounding the team despite a disappointing 2019, the Cowboys have a lot of work to do this offseason to fill out their roster.

Let’s assume for a moment that Dak Prescott and Amari Cooper are back. All signs are pointing to this being the case and there’s no reason to think they won’t be continuing to find that connection in the fall. With those two coming back almost the entirety of your offense will return in 2020 from a stellar 2019 season.

With Prescott and Cooper returning to the fold, Jason Witten and Randall Cobb remain the only players who contributed in a significant way in 2019 heading to free agency. The hiring of Mike McCarthy all but assures Cobb will be back while Jason Witten may be finding a new team if he hopes to continue playing football in 2020.

The depth on the offense has some questions with Tavon Austin, Joe Looney, and Cooper Rush free agents (Rush is a restricted free agent).

On defense, the potential losses stand out a whole lot more. Robert Quinn, Byron Jones, Anthony Brown, Maliek Collins, Antwaun Woods, and Michael Bennett all played significant snaps for the Dallas Cowboys and all are expected to be free agents. There is some doubt about the Cowboys’ desire to re-sign Jones to a long-term contract but may feel better about bringing Robert Quinn back. Defensive tackle will need a lot of work. Though Antwaun Woods is an exclusive rights restricted free agent, the Cowboys should look to upgrade the position in free agency or the draft and there will be options to do so.

Defensive Tackle

The Cowboys have a lot of work to do to fill out the defensive tackle spot in free agency and the draft. At the moment Tyrone Crawford and Trysten Hill are the only defensive tackles that played snaps for the Cowboys in 2019. Both of them were limited however, Crawford due to injury and Hill due to readiness. There’s a strong possibility that Crawford isn’t with the team in 2020 as the Cowboys could save $8 million in cap space by releasing him.

It’s pretty likely that Woods is back given his status as an exclusive rights free agent, but a lot of that will depend on how the current staff feels about him. Woods is a gamer that provides quality snaps along the defensive line but hasn’t been consistent enough.

Free agency could provide a great opportunity to upgrade the defensive tackle position even if the Cowboys wanted to bring back Woods as well. If the Cowboys went into 2020 with Woods and Hill as the backups on the interior they’d be in a much better position than if they were the starters.

The Cowboys need to bring in at least two more players at defensive tackle in addition to Woods and Hill.

Safety

Same song different year for the safety position and the Dallas Cowboys. Will this be the year the Cowboys invest to upgrade the safety spot?

Much like last year, it seems like both free agency and the draft set up quite nicely for the Cowboys to find a player that fits alongside Xavier Woods. There are both veterans and incoming draftees that have the versatility to play free and strong safety, which would allow the Cowboys to mix and match at the position.

The problem is, the Cowboys have been averse to investing premium picks or cap dollars to find a player to upgrade the position. Is this a position the Cowboys front office just doesn’t value?

Last year in the draft, Kris Richard stood on the table for Xavier Woods and signed off on the Cowboys drafting Trysten Hill, but Stephen Jones and Will McClay aren’t innocent from neglecting safety.

They’ve had opportunities, even in the second and third wave of free agency, to make a signing that could have an immediate impact whether it was a lesser name like Tre Boston or a big fish like Tyrann Mathieu, Earl Thomas, or Landon Collins. For several years now, the Cowboys have opted to allocate resources elsewhere. There’s hope that with a new coaching staff there comes a new way of valuing positions, but that remains to be seen.

Cowboys Nation could be getting its hopes up for Grant Delpit, Xavier McKinney, Antoine Winfield Jr, or Ashtyn Davis while the Cowboys front office is looking in an entirely different direction.

Cornerback

One position of need that complicates things in both free agency and the draft is the state of the cornerback position for the Dallas Cowboys.

Byron Jones is a free agent this year and despite his talent, both Will McClay and Mike Nolan have made comments that could signal the end of Jones’ tenure with the Dallas Cowboys. Both Jones and fellow free agent cornerback Anthony Brown are both set to see an increase in pay this offseason with teams always looking to spend money on cornerbacks with a lot of experience.

If Jones and Brown depart in free agency, that leaves only Chidobe Awuzie, Jourdan Lewis, and Donovan Olumba as the only corners returning to the 2020 squad. However, Awuzie and Lewis are entering their contract year and will be free agents this time next year leaving a massive talent need at cornerback come next offseason.

Even if they bring back Jones or Brown, they still need to look at the position with the potential vacancies that could develop this time next year. Cornerback is a position that is better to be eased into. If they can spend the 2020 season preparing the eventual starter in 2021 that would be more advantageous than drafting one in 2021 to insert as a starter the following fall.

The reason cornerback complicates things is that it creates one more position that you have to seriously consider with a premium pick in the top 100 of the draft regardless of who you bring back this offseason.

Tight End

At the moment, Dalton Schultz and Marcus Lukas are the only players set to return to the tight end position in 2020 with Jason Witten set to be an unrestricted free agent and Blake Jarwin to be a restricted free agent. It’s a near guarantee that Jarwin will return as he had a ton of success for the Cowboys in 2019 and would be the presumed starter unless they made a significant addition in the draft or free agency.

While many are big fans of Jarwin’s ability to catch the football, he still has a lot of work to do as a run blocker and this is an area where the Cowboys could look to add a player. They could either bring in a player like Eric Ebron, Hunter Henry, or Austin Hooper who are good players in both the run and pass game. On the other hand, they could feel good enough about Jarwin’s ability as a pass-catcher that they bring in more of a run-blocking tight end to supplement what Jarwin can do.

Drafting a tight end has its downside. Aside from quarterback, tight end might be the position that requires the most difficult transition in the NFL. Rookies have to learn the nuances in both the run and pass game, which requires a much larger learning curve than say wide receiver or running back.

Edge Rusher

After a bounce-back 11.5 sack season, Robert Quinn could be headed for a big payday leaving edge rusher a serious need for the Dallas Cowboys. Mike Nolan wants to be able to function in multiple defensive fronts (3-4 and 4-3), the Cowboys might look for a player that is able to function as both a 4-3 defensive end or a 3-4 outside linebacker and allow Quinn to walk away altogether.

Though they may use a variety of fronts, the Cowboys will still be in nickel packages on defense around 70% of the time in the modern NFL. That means having a guy like Quinn who can play the edge regardless of the front is helpful. You won’t be asking him to drop into coverage much anyway.

That said, if Quinn were to walk in free agency, the Cowboys would need to look to free agency or the draft to fill that need as Dorance Armstrong would be the next man up to play on the right side of the line. He’s shown some things in his first two seasons, but not enough that you’d be confident starting the 2020 season with him as your full-time right edge rusher.

Wide Receiver

Again, assuming that Amari Cooper is back, the Cowboys still have to figure out what they want to do with their wide receiver depth chart. There’s still a pretty good chance that Randall Cobb is back to fill the slot wide receiver role, but beyond that, the depth chart has question marks.

Cedric Wilson can’t stay healthy long enough to make an impact. Devin Smith wasn’t consistent enough when given an opportunity in 2019. Tavon Austin is heading for free agency and would be unlikely to return. Ventell Bryant, though he offers a lot as a special teams player isn’t someone you want to rely upon to backup Cooper or Michael Gallup on the outside.

There are some interesting names in both free agency and the draft for the Cowboys to explore. Even if they bring back Cobb and Cooper they have to add someone who can be a more effective backup on the outside than Austin was in 2019.

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Stephen Jones and Will McClay have a lot of work to do this offseason to retool the Dallas Cowboys with the hopes of making a run to get back to the playoffs in 2020. There will be little patience from a fan base that is starved for deep playoff success so the mandate is there for them to make significant additions in both free agency and the draft. They can’t afford to sit back and watch some of the better free agents get snatched up over a few million dollars. They also can’t afford to have a draft class give them as little as the 2019 draft class did.

They have to swing big this offseason and they have to hit some home runs. Much like they did with the Robert Quinn and Michael Bennett trades, the Cowboys have to take some calculated risks and hit on those risks. They also have to get back to the success in the draft that they had in the 2016 and 2017 classes that provided a big part of the core group of this team.