Reminder - the Catholic Herald is a British newspaper.
I don’t think you can be gentle as Pope this time around. Strangely enough, I think Dolan will get it, but I’m not happy about this, even though I like him personally. He’s more blustery than O’Malley, but I don’t think he’d be very firm. I’m not sure O’Malley would be firm, either.
The only positive thing with O’Malley is that he is very tied in with the Neocatechumenate, a Spanish lay movement that had a lot of dubious things about it (in my opinion) but that did seem to produce very faithful Catholics. When I was in Madrid for World Youth Day, the Boston Archdiocese sent what seemed like thousands of young people in the movement who were out there cheering the Pope, singing very beautifully, carrying banners in procession, and bonding with the other members of the very large worldwide Neocatechumenate movement (which isn’t just young people, but is into its second or third generation).
So who knows?
Orthodoxy in doctrine doesn't seem to be a concern of his. Whether he's personally orthodox or not, he surrounds himself with people who aren't -- the infamous Fr. Hehir is in his "inner circle" of advisors; also Jack Connors, a huge bundler for Obama -- these off the top of my head. There seems to remain a significant "gay network" among Boston clergy. Finances are irresponsibly handled. Mass attendance is way down under him. See Boston Catholic Insider for the details.
I'm not sure why he is considered by anyone strong on life issues. The Boston Archdioces is (to my mind conspicuously) absent from the list of Catholic entities suing HHS over the mandate; an archdiocesan spokesman, when asked about it, said in essence "Other groups are suing; we don't have to," although -- from what I've read -- the law firm of Jones, Day is handling the cases pro bono. Of course, O'Malley has been silent on similar issues in MA.
I'm pinging a few old FReepers who haven't posted lately. I don't know if they still look in, but they would probably have something to add!