Sure I would agree, and certainly this is something every team goes through at some point. The issue is the Cowboys seem to have an unproportionate issue compared to the rest of the league when it comes to signing players at the last moment, and spending money in March/April/May/June.
Since 2020 here are the major extensions the Cowboys have had (3+ years/$8M+):
- OSA - March 4th - About to be FA
- Dak - September 8th
- Lamb - August 26th
- Steele - September 3rd
- Hooker - August 4th
- Diggs - July 25th
- Dlaw - March 14 (Pay cut)
- Gallup - March 13th (About to be FA)
- Dak - March 9th (About to be FA or 2nd year tag)
- Cooper - March 16th (About to be FA)
There are simply zero examples of guys signing monster deals either right before they hit FA or late in the offseason. Now pre 2020 I don't think the Cowboys were quite as cheap of an organization, but you still had mixed data to go off of. Seems like it was more of a transition period with how they elect to spend money.
DLaw was signed early, however I think that may have been the year he forced their hand with putting off surgery in 2019. Jaylon Smith, Zeke both late summer singings in 2019, but then you also had Jarwin done early, Quinn signed early, Martin was reasonable with early June extension. Witten was an early offseason on his last major deal in 2017, etc.
As far as recent history though I simplys struggle to see how the Cowboys manage extensions is anything but a result of the philosophy of ownership. Everything suggests that they prefer to wait it out. Jerry has even suggested that himself many times.
