Plankton
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I doubt we can offer a second Tag for 2021 and its not really due with the tight CAP, though that is the fundamental issue. It's because Dak can refuse to sign until the last minute which will stop the Cowboys from signing much needed Free Agents.
If we offer the second Tag we are going to need to keep back $37.7m to cover the payment.
The CAP (as per OVER THE CAP), will rise by roughly $17m, this plus a carry over from this year $11m, gives us just $10m to spend.... but if Dak leaves it late we're going to have no one left worth getting (not that $10m's going to get you much).
This is not an issue, and will not prevent them from tagging him again. The Cowboys, as an organizational philosophy over the last few seasons, have not been active in the big ticket sphere of free agency. They play on the fringes. And, the cap isn't going to rise after this year. At best, it will be flat after they reach an agreement with the NFLPA to borrow against future revenues to avoid a cap reduction of between 30M and 50M (depending on whether fans attend games or not, and if there is even a full 2020 season).