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I made a post about the dangers of nepotism to the health of the Patriots culture a couple of years ago and got more negative (even angry) reaction here than positive. Emperor's clothes.
Every leader and leadership team of every organization, now and in the past, has blind spots and repeats the same mistakes over time. What determines success is the ability to take feedback from people outside of the leadership, and discover those mistakes.
There's no doubt that Kraft family and Belichick's strengths have overcome a lot of that up to now but at some point, it catches up. Is Stephen Belichick the best possible candidate for the responsibilities he's been given? Odds are very low on that. So the overall health of the organization is being harmed by the use of privilege granted to Belichick, due to his heretofore otherworldly success. It happens. The price is always paid. And as you point out above, it usually comes in small doses that add up and lead to outcomes (like people leaving early) that are somewhat opaque at the time.
Maybe, but Steve Belichick coaches the safeties. I'm not sure that was really an area of concern. Increasing Joe Judge's responsibilities by making him both the ST and WR coach might have been a problem.