That's a really good question!
Dolan was appointed by BXVI. That said, Dolan actually had a reputation for orthodoxy before he got to NY, although he was always probably more Dem than Catholic.
It could be that he thinks his stupid responses are what the Pope wants, although I honestly don’t think that’s the case. But it certainly saves Dolan any effort. He can go out and schmooze with the gays, drape his arm around Cuomo or De Blasio, and feel he’s just the coolest bishop in the universe.
I suggest he run and read Luke 16.
There’s nothing new under the sun. A reading of Numbers re: Korah, Dathan and Abiram and a perusal of Balaam may be in order as well.
As is said in Psalms...
Let another take his office.
But hey, we wouldn’t expect Satan to bother with the usual heathen on the street if he could get a bigger catch. We are all human, with free will. We have all sinned, fall short and are working out our salvation.
Remember, re: letters to the churches, the corruption was from inside, Christians, not outsiders. Pride must be checked when offering correction... with prayer and humility, lest we pile sin on sin. You correct your addict brother, not because you’re higher or better than him, but because he’s hurting your father/family, giving bad example/corrupting his other/younger siblings and ruining his soul... and others through what he does, rather he realizes it or not, is ready to receive it or not.
We all have to answer to the Lord.
Trust in God and pray for him and all of us.