This is a for-the-record historical observation, since (alas!) I am about the only one on Team Atlantic in a position to offer it.
I am just a few years younger than Mitt Romney (also Bill Clinton and GW Bush -- the three of them all born within an eight-month stretch in the early Baby Boom). So I can remember the era, though not the prep-school atmospherics nor all-boys school dynamics, of the now-infamous Cranbrook haircut story.
Part of what Mitt Romney has said rings entirely true to me, concerning those times. That "sissy" or "effeminate" kids would have been picked on, but that they wouldn't have been openly known as gay, is how it was. Teenagers were and are cruel, especially to those who seem "different." And in that era, homosexuality as a reason for different-ness wasn't something people talked about. (Skeptical? I give you the closeted art-director Sal, in Mad Men -- and he was in New York.) As I mentioned after Barack Obama's announcement that he had changed his mind on same-sex marriage, it is painful and embarrassing for me to remember the casual "faggot" taunts of those days, and what it must have been like for my friends and schoolmates who were gay but couldn't say so.
So I believe Romney when he says that he wasn't aware then that some of the objects of his "pranks and hijinks" might have been gay. And good for him for saying that he regrets any harm he caused.
But ganging up on someone, holding him down, and against his will cutting off his hair? Even for the time, that would have been unusually cruel.
I knew a lot of tough kids at my big public high school, and I kept my wary distance. They would get in fights and beat people up and generally make others afraid. But the worst you would hear is that someone had gotten stuffed in a locker, or "pantsed" and left in his underwear on the football field, or "pinkbellied" (held down, and slapped on his bare stomach), or, at worst, ganged-up on in the boys' room and dunked head-first in the toilet bowl. All this happened, and fortunately not to me. But the next day, no one would necessarily know about it -- not even the parents, if the kid didn't tell them when he went home. Cutting off someone's hair is different. It's a shaming ritual that is meant to last -- and that the victim must carry around on his person for weeks.
No doubt the dynamics were different, in ways I can't fully imagine, at an all-boys school, and with boarders rather than kids whose parents would say that night, "What happened to you? Who did this???" ["Umm, dad, it was the governor's son..."]
So to end this historical note: cruel teasing of "sissies" sounds unfortunately representative of the era. Cutting off a sissy's hair does not. And assuming it happened, as a number of Mitt Romney's classmates have attested by name, we are left with Romney's claim that he "doesn't remember" the episode. I think it's worse for him if he's telling the truth.