Why do the Cowboys wait so long to extend their players contracts?

They have a history of being slow to sign the star players on their own roster. I suspect that the agents of those players have found a way to "work" the FO for the most money possible. It seems that if they wait and wait and postpone talks that the FO gets nervous and tends to cave. The Jones boys end up coughing up maximum bucks. IMO Jerry and Stephen are poor negotiators with players and agents.

That also may be why the FO is timid is dealing with star FA fresh off other rosters.
 
They fear setting the market. That's why they always reference "letting the leaves fall".

They always end up skewing to the top end of the market or in Dak's case setting the market. So, I can never understand why they wait so long. I can only surmise that they actually don't know what they're doing when it comes to these high profile negotiations.
 
They in fact wait a year too long to sign players to big contracts (jags aside).

Honestly, I don’t think they know what they’re doing.

Or…

They just want to pocket cash and enrich themselves, in fact their cash spending amongst the most frugal teams.

Then, they can claim there’s no cap room and that they are hand cuffed by the CBA/cap.
It’s the cap.
 
It's a mystery to those who feel it's not to the FO's advantage to do so.

They tend to claim that it helps them, when it really doesn't. Go figure.

They fear 'setting the market.' Apparently, they don't trust themselves.
 
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What is a reason why we wait so long until the last minute to sign our players? What do we get out of doing this, it seems weird like they like this they seem infatuated with it! If the goal is to make a news story and not get ahead of these deals early, them I'm lost!

You see teams extend players early possibly after their 3rd season, why wait until its late to start getting things done. We're tight with our spending, but we wait and wait and end up spending more by taking our time! Please give your thoughts
Is the question why do they wait so long in the offseason to get contracts done, or why do they wait until contracts are about to expire or have expired to sign new deals?

The answer to the first question is, they are stupid. They have no feel for the market. The have no feel for the players or their agents. They don't know what they are doing.

The answer to the second question is a larger discussion but I think most teams wait until contracts are about to expire. I think players prefer to wait in many case because they want the threat of open bidding to drive their price up. Some may want to see if they can get more on the open market. What they risk is injury which might drive down their contract value. But then they sign one year deals so they can prove they are the same player then hit the free market again.

On this issue, I can argue both ways. If we are talking about a 1st round pick there is always the option year to keep them for a 5th year. For everyone else to resign them after 3 years or 2 years, they would have to prove they are good enough very quickly, or the team would have to take a chance on them improving. I would be against signing a 1 year wonder to a longer term deal. I think the Cowboys wait because there is always the threat of injury. Then the team is stuck with a long term deal for a player who may never be the same or he is diminished for a year or 2.
 

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