The great thing about this is that none of us know anything, so we are free to speculate, as long as we do so acknowledging that we don't know what the heck talking about. Any of us. We don't know what we're talking about. We're guessing.
That said, my take, from the day I heard about the Garoppolo trade, has been that it was Kraft's decision and that he made the decision beccause he realized how very, very badly he had treated Brady during Deflategate. The only foundation in fact that I can offer for that is that building for the future with Garoppolo is consistent with every major personnel move that BB has made in 18 years...move on from a guy a year too early rather than a year too late. I even think Belichick was ready to endure an awkward, cap-busting transition year in 2018-19 with the Pats paying $10+ million for Brady not to play, at least in New England. As we can surmise from Brady's history at Michigan with Drew (who's he?) Henson, it was very unlikely that Brady would have stayed on the NEP Roster sharing time with Garropolo or backing him up...nor should he have done so.
As for Belichick's personal feelings, angers, etc.,...well, that's pure speculation and I won't go there. I'll just stick with the few facts we now know.
Garoppolo, who seems like the real deal, is gone. Belichick, according to too many reports for it not to have some basis in fact, is making life very uncomfortable for Brady's alter-ego, Alex Guerrero, allowing Guerrero (fraud, genius, manipulator, Yoko...whatever you might call him) to treat only Brady on the premises and casting a cloud over his practice. There are a million possible conspiracy theories there...but there seems to be enough money or reputational concern involved that everybody is keeping quiet (so far). Brady is playing at an MVP level at the age of 40.
Here's where I'd disagree a bit with Cowherd. Yes, I think this is heading for a messy end. Belichick is the acorn that fell from the tree of Parcells and had the temerity to grow into a bigger Oak. But, like Parcells, he will do what he wants at the end, the only difference being that he has a chance to do it after winning his sixth Lombardi as HC.
Also, Cowherd is leaving out one other possible landing spot for Belichick.
Since we're on the topic of Bill Parcells, The New York Tabloids have started whispering that Belichick could go full circle and end up as HC of the NYG...or as GM with Josh as HC. If Cowherd is looking for a "Belichick Revenge Scenario" (and I'm not agreeing with him there), that would be the ultimate.