Impending contract decisions could bring about some distressing times for the Dallas Cowboys

The NFL Draft is less than 50 days away. Free agency starts in a little over a week. And the deadline to designate players with the franchise tag is almost up. If you’re the Dallas Cowboys, all of these circumstances and events are extremely important as they play a big part in the future of this team. Which free agents are they going to keep? What kind of cap burdens will the team be facing down the road? And what new rookies will be wearing starless helmets come training camp? There are so many questions. Slowly but surely, we’ll get the answers in what could end up being one of the more interesting offseasons in recent Cowboys history.

With everything that is going on, it’s a good time to just take a deep breath, sit back and try to gather all your feels for what’s happening here.

For the big guns, it’s just a matter of when

I can’t tell you how many times I’m asked whether or not the Cowboys are going to keep Dak Prescott. I’ll be walking in the halls at work and someone I haven’t seen in a long time will pass, and instead of “Hey, how’s it going? How’s the family?” I’m immediately pressed with “are you guys going to lose Dak Prescott?” The answer is always “No. Definitely no. And absolutely not.”

Considering how much the media toys with this notion, I get the confusion, but Dak Prescott is playing for the Cowboys in 2020, and beyond. I’ve never been more certain about something that if I’m wrong, I would put on a blonde wig and squeeze into my wife’s pink Romo jersey every Friday until the start of the season. Yes, that’s an unpleasant consequence, but I think we can all agree that it would never happen.

Anything past that however, brings about a little uncertainly. I would’ve doubled up on that blonde wig bet for Amari Cooper just the same if it was a couple months ago, but now there is just enough doubt in my mind that I’m not willing to risk it. Do I think he’s going to play for the Cowboys this season? Absolutely. But here it is, the second week of March, and Cooper remains unsigned. And it doesn’t make matters any easier that this whole CBA/one-tag or two-tag thing could be throwing a wrench into things. If Cooper somehow enters free agency, that’s a problem. With every WR-needy team now in play to offer up Cooper the best deal, the Cowboys would end up losing him.

Luckily, that’s not going to happen, right? As sure as the day is long, negotiations are going to pick up steam and things will come together quickly. When will that happen? Probably near the final hour because the Cowboys are notorious for dragging these things out as long as they can before they finally say “uncle.” I couldn’t tell you if it will be Prescott or Cooper who gets their new deal this upcoming week, but somebody has to so their franchise-tag plan can buy them the time they need to sign the other.

This “letting Bryon Jones walk” thing is upsetting

When the Cowboys moved away from their absolutely maddening negligent ways of free agent spending to this frugal conscientious manner of cap-watching, it brought about great satisfaction as the team’s years of booming dead money hits dissipated. The Cowboys carry less than $2 million in dead money this season, and the bulk of that is courtesy of one Taco Charlton.

While being cautious with outside free agents makes perfect sense, considering the bang for the buck is statistically heavily unfavorable, it’s a little perplexing why the team isn’t trying harder to keep Byron Jones. Maybe he and his reps are asking for some lucrative amount to where the Cowboys front office isn’t going to waste anyone’s time.

It’s hard to wrap your mind around how a team wasted three years playing him out of position. But then it’s absolutely cretinous that when they finally figure it out and see that he excels at his new position, they up and decide he’s not worth the money. Jones isn’t the best corner in the league, but he is certainly one of the better ones. When you consider his character, durability, and demonstrated ability over his two full seasons at the position - this has misstep written all over it. What is this front office thinking?

A week ago, we asked when was the last time you were upset about the Cowboys losing a player to free agency. When Jones departs, that will be earn my nod as the most heartbreaking free agent loss.

This next draft is going go be scary

All drafts are important, but the 2020 festivities are crucial for a number of reasons. For starters, the losses expected in free agency is going to hit the defense hard. If you look at the last decisive game the team played last season (Week 16 in Philadelphia), of the eight defenders who logged the most snaps - six of them are free agents. That includes Byron Jones, Robert Quinn, Maliek Collins, Michael Bennett, Sean Lee, and Jeff Heath. When you add players like Anthony Brown, Kerry Hyder, and Chris Covington - that’s a huge laundry list of holes. The Cowboys will retain some of these guys, but there is some good talent here that will be leaving in free agency.

Not only is there going to be some added pressure to land some day one starters on defense from this draft, but you also have a new coaching staff that will interject their own input into the draft process. How is that going to work out? Will they show the same patience they’ve always had or will they drift to a more need-oriented approach after suffering such a big hit in free agency? The team has a history of drafting well, but there are no promises that will continue.