The Dallas Cowboys have done great work the last few years of shedding bad contracts and getting out of “salary cap hell.” However, even this relative fiscal paradise of 2019 isn’t perfect. Today, we’re going to look at the five worst deals that Dallas still has on the books.

These contracts are only active as of now, in the middle of May, and could be gone by the time we gets to Week One. We’ll discuss those possibilities as we go through each player.

What you’ll realize fairly quickly with this exercise is that it’s a stretch to even say the Cowboys have five “bad” contracts on the team at this point. That’s how well the front office has done in learning from the past and getting things to a much more manageable and equitable point throughout the roster.

Maybe that changes in a few years. Some of the big contracts on our All-Pro offensive linemen may lose value as those players start to decline with age and/or health issues. Or perhaps the upcoming new contracts for Dak Prescott, Amari Cooper, Byron Jones, Ezekiel Elliott, and others will turn out to be retrospective mistakes.

But those are conversations and articles for future offseason. For here and now, 2019, here are the five worst contracts on the Dallas Cowboys roster.

DL Tyrone Crawford – $10.1 million cap hit

I know I’ve been picking on Crawford a lot lately, but that’s what happens when you have easily the worst contract on the roster. Tyrone has the second-highest cap hit on the defense and sixth overall on the entire team, and that’s an obvious imbalance compared to where he ranks among the Cowboys’ top players.

This situation isn’t Crawford’s fault. Dallas thought they were making a shrewd move by giving Tyrone a sizable contract back in 2015. They expected him to blossom as the 3-tech DT under Rod Marinelli.

That boom never happened, and as a result Crawford’s contract ultimately became a bust. He’s been valuable as a leader and having DE/DT flex, but he’s never been a top player on defense even when he was the highest paid.

I wrote more extensively on what Tyrone’s future with the Cowboys might be, especially with the June-1st date looming for potential roster cuts. His job security has taken some big hits lately with the drafting of Trysten Hill and now legal issues, which could result in a minor suspension for Crawford in 2019.

We’ll see if Tyrone Crawford makes it to the 2019 roster. He still has value with his versatility and generally solid play, but that overpaying contract could ultimately be his demise.

WR Allen Hurns – $6.25 million cap hit

The only other contract which is truly “bad” for the Cowboys belongs to veteran receiver Allen Hurns. It gives him the 11th-highest cap hit on the roster, and this for a guy who projects to be no higher than fourth on the WR depth chart.

The week before free agency opened in March, Dallas picked up an option to keep Hurns in 2019. It’s always felt like an insurance move; Hurns can be released with just $1.25 million in dead money at any point this offseason.

Dallas is likely hanging onto Hurns until they get through the preseason without any injuries to Amari Cooper or Michael Gallup. It’d be nice to have Allen if something happens to them; he has plenty of starting experience and can be an every-down receiver. Guys like Randall Cobb or Tavon Austin aren’t built that way, while Noah Brown isn’t experienced enough.

Assuming everyone gets to September intact then I expect Hurns will be released. It’s hard to imagine Dallas carrying him as a backup with that cap hit, and especially if they have younger guys like Brown or Cedrick Wilson that they want to utilize.

So no, Hurns’ contract shouldn’t cost the Cowboys for long. If he stays then it’s because he’s needed for a starting role, in which case $6 million is reasonable. But if he’s going to spend most of the year on the sideline, Dallas has an easy out that I expect they’ll utilize soon.

LB Sean Lee – $6 million cap hit

This is another one where how bad the contract is could shift depending on how much the player is needed in 2019. Even with a negotiated pay cut, Sean Lee’s still making more than most of the starting defense.

Paying Lee this much to play SAM and then backup Smith and Vander Esch on the nickel is a bit high, even for what he brings as a mentor and coach on the field. But Dallas was willing to overpay for the intangibles, plus the hope that Lee could still play at a high level if called upon.

The biggest concern with Sean Lee, as it’s ever been, is his health. He can still ball but has reverted to injury-prone issues in recent seasons. Perhaps a lesser role with fewer snaps will help in that area.

Again, I don’t even know if I’d call this a “bad” deal. We have yet to see how much Dallas plans to rotate Lee with their young studs, and he brings things to the LB room that a guy like Damien Wilson never could.

The major liability here is if Lee gets hurt, in which case Dallas basically has a solid chunk of cap space tied up in an assistant coach.

TE Jason Witten – $4.25 million cap hit

You can apply some similar logic to Witten’s deal from what we just discussed with Sean Lee.  If he contributes on the field then it’s not a bad deal. But if age and time away from the game have caused Jason’s skills to slip too far, then this is a lot of money to pay for a backup TE.

Like Lee, Witten will hopefully offer a great deal as a mentor for Blake Jarwin, Dalton Schultz, and any other young tight ends. He can’t make them any more talented, but he can at least help maximize whatever potential they have.

But again, without actual on-field contributions, that mean you’re spending valuable salary cap space on coaching. That money could’ve gone to someone like Jared Cook for a more simple and immediate boost to your offensive firepower.

As we said at the outset, most of these contracts are only conditionally bad. If Witten’s year off allowed him to heal and rest and come back with renewed vigor in 2019, then it could wind up being a great deal for the Cowboys.

Father Time may ultimately be undefeated, but he doesn’t win every round. Hopefully Jason can fight him off for at least one more year.

DE Taco Charlton – $2.74 million cap hit

Taco’s disappointing start to his NFL career has made his rookie contact, which is usually team-friendly, a bit of dead weight on the Cowboys’ books. Unless Charlton take a big step forward this year, the Cowboys are stuck paying him like a significant contributor for the next two seasons.

Dallas would get no cap relief cutting Taco this year; his cap hit stays roughly the same if cut after June 1st. It would also push another $1.35 million in dead money onto 2020. Therefore, unless the situation between team and player has become truly toxic, or a trade partner emerges, the Cowboys should hang on to their 2017 first-round pick at least thru 2019.

Ideally, Charlton will emerge this year as a more consistent and motivated roleplayer. There’s little chance that he’ll start with Robert Quinn coming in, but Charlton could still claim the role of a major rotation piece if he’s had some more development.

If that happens, Taco’s deal will become far less worrisome. That’s a modest salary for a solid backup at most positions, and especially at defensive end.

If Charlton doesn’t improve, though, Dallas will finally be able to get some savings if they cut his deal in 2020. In that scenario, he probably isn’t around long enough to make this list a year from now.

~ ~ ~

What makes a contract bad or good is subjective. You might look at those huge cap hits on deals for guys like DeMarcus Lawrence or Zack Martin and think they’re the biggest problems. But if you’re getting All-Pro play at fair market value, you really can’t criticize those salary numbers.

It will be interesting to see what happens the next few years with guys like Travis Frederick and Tyron Smith, whose health issues could change how we perceive their contracts. Both are still young enough to play at a high level, but could we adding one of them to this list in the next year or two?

A few years from now, we make look back on 2019 as an anomaly. Having to reach to find enough contracts to make this list is a great problem to have.

I just hope it stays that way.