The curious case of Leighton Vander Esch has the Dallas Cowboys trying to determine what happens next with his contract. Initially, the team was roundly scolded by fans and pundits alike for selecting the former Boise State star linebacker with the 19th-overall pick in the 2018 NFL Draft, but the joke was on them, because Vander Esch burst out of the gate with a dynamic rookie season that led to him being named to the PFWA All-Rookie Team -- along with garnering a Pro Bowl nod and second-team All-Pro honor. The problem is he's been battling durability issues since, and that looms large as the Cowboys try to figure out his fifth-year option.

And the retirement of Sean Lee adds to the question marks at the position. 

As a former first-round pick, the team has the right to pull that trigger and secure Vander Esch through the next two seasons, but it remains undecided on that front, and largely due to challenges with his availability -- sources tell CBS Sports. And while the subject could've been put to bed recently by Stephen Jones, the Director of Player Personnel instead put a pin in it until after the 2021 NFL Draft, and that's a clear sign they're not exactly ecstatic about hopping aboard that train at the moment. If they were, much like teams around the league who are already making the fifth-year jump, the Cowboys would have as well. 

"We haven't made that comment or made deep discussions on that yet," Jones told 105.3FM the Fan. "Certainly it will be coming up for us, and we'll be discussing that after the draft. But as you said, it's right around the corner."

Indeed it is, with the NFL deadline for executing fifth-year options standing at May 3. 

There are other factors outside of Vander Esch's injury history that complicate the matter, with the new collective bargaining agreement being the other elephant in the room. Unlike years past, the new CBA establishes a financial trigger that would fully guarantee the fifth-year salary once the team executes it. So while Vander Esch meets neither the Pro Bowl criteria -- replacement Pro Bowls do not count in the new escalator (his 2018 nod was an injury replacement for Luke Kuechly) -- nor the playing time criteria to push his pay higher, the Cowboys would have to fork over every penny of the predetermined $9.145 million; and that is regardless of what happens after they do it.

In other words, they'd be locked in no matter how many games Vander Esch does or does not play next year.

That's not exactly ideal for a Cowboys front office that operates with a tight purse string regarding their salary cap. Truth be told, if they weren't faced with having missed 13 regular-season games over the past two years, the decision would be made easier when factoring in how the cap will presumably be much higher in 2022 -- with new TV contracts in hand as well as an expected return of fans to stadiums around the league. From the Cowboys standpoint, however, they'd prefer to at least see what they walk away with in this year's draft before fully guaranteeing Vander Esch's salary.

The 25-year-old isn't without leverage of his own, though, as noted in the retirement of Lee and inherent in the regression of former second-round pick Jaylon Smith. And with Smith set to hit the team's cap for $11.8 million in 2022 -- having signed a five-year, $64 million deal in 2019 -- there's a decision to make there as well next offseason, putting the Cowboys in a precarious position if Vander Esch is allowed to enter a contract year in 2021. There is a chance Smith can bounce back under the tutelage of defensive coordinator Dan Quinn and, as such, would justify the financial hit.

But there's also a chance he doesn't, and puts the Cowboys in a position where they may have to decide between keeping him onboard or re-signing Vander Esch as an unrestricted free agent -- who might command more money if he can put together a full season that also sees him produce at the All-Pro level he did just three years ago. There's the added scenario of Vander Esch and Smith having fantastic seasons, in which case you wonder if the Cowboys are willing to invest that much cap capital into the linebacker corps. 

For a usually frugal front office that went toe to toe with its own franchise quarterback, this is where the fabric gets itchy. 

The team likes what it has in young players like Luke Gifford and Francis Bernard, but are the Cowboys prepared to hand the keys over to them just yet? And/or to whomever they draft in 2021, assuming they land a linebacker in the premium rounds?? Needless to say, as quiet as it's been kept, it's a position of need in Dallas that must be addressed beyond simply the signing of Keanu Neal to operate as a flex player (read: Lee replacement in 2021); and particularly with a solid veteran like Joe Thomas leaving in free agency for the Houston Texans

"Whether it's Jaylon, who obviously we have signed, or a guy like Leighton, who we know is going to be coming up for a contract -– you want to have depth there," Jones added. "And as I mentioned earlier, I think we can use defensive help, probably at every level."

There are more pressing needs in the secondary and on the defensive front at the moment, but the need at linebacker will again take center stage next year, and only a few seasons removed from the Cowboys feeling as if they had it figured out. But hey, no one ever said managing an NFL roster was easy.

And Vander Esch will find out soon enough if he'll be a free agent when the season ends.