I don't think this article is well written. It creates some confusion. For example:
The NFL might have decided to begin planning for paying $14.1 billion not by telling the teams to start figuring out how to come up with $440 million each when the appeals are exhausted but by creating a global fund for paying it all off. Then, if the NFL wins the case, all of the money will flow back into the cap.
There are two things at play here. Yes, if each team has to pony up $440 million each, that could affect future expenses (which includes players' salary) but it should have little effect on the cap. Cap is based on revenues. The potential $14B fine is not a hit to revenues, it's an expense. So to say if the NFL wins the appeal, the $14B goes back into the cap is a weird way to put it. And I suspect the NFLPA would have a lawsuit ready if the league tried to claim the $14B was a hit to revenues and not a cost of doing business (which it is).
Now what could affect the cap is the NFL losing the appeal and the league shutting down ST. I have no idea what the annual revenues are from the service but nevertheless it would be a hit to revenues and as such the calculation of future caps which are based on future revenue projections.
I think what Jerry is saying is that teams will start counting their pennies a lot harder if the fine sticks and each team has to contribute over $400 million to pay said fine.