Yes, it is correct to use a period and an apostrophe to make a name that ends in "Jr." possessive, but it's also distracting, so it's better to rewrite your sentence.
Donald Trump Jr. has been in the news a lot the last couple of days, and I’ve seen some pretty funky punctuation on the “Jr.” part of his name.
On Martin Luther King Jr. Day, we talked about whether you should look at that word “Jr.” and put a comma before it. I told you people were more likely to use a comma in the past than they are today. The AP Stylebook, the Chicago Manual of Style, and I recommend that you don't use a comma. But it is a style choice, and “The New Yorker” uses the comma, which led someone to write a headline that read
It’s a traffic jam of punctuation!
Unfortunate side effect of the scandal is this period-comma-apostrophe bullshit from the New Yorker. pic.twitter.com/ITijnSXOWn— Michael Colton (@mikecolton) July 11, 2017
On Twitter, Michael Colton, a film and television writer, complained about the punctuation in a tweet that right now has more than 13,000 likes. He’s pretty funny. Today he’s joking that he just sold the rights to his tweet to Lionsgate. At least, I think he’s joking.
Understandably, “The New Yorker” got a little defensive. Andrew Boynton, the head of the copy department, wrote a response explaining the punctuation, essentially saying the magazine’s style is to put a comma before (and also therefore after) “Jr.” And when that’s your style and you have to make a name possessive, that’s what you get. It might look bad, but it’s correct.
I’ve never seen a style that says it’s OK to put a comma in the middle of a word before the apostrophe-S, and Chicago seems to specifically recommend against it, but that’s what house styles are about. You get to say, “This is how we do things here,” and it doesn’t matter what other people think.
As far as I know, “The New Yorker” is also the only publication that puts a diaeresis over the second O in the word “coöperate.” A diaeresis is a mark that looks like an umlaut—the two little dots over a letter you often see in German—but the diaeresis is there to show you that the letter starts a new syllable. It’s there so you know the word is pronounced “co-operate” and not “coop-erate.” So this isn’t the first copy editing choice that makes “The New Yorker” seem a little out there on its own.
“The New Yorker” headline is the ugliest one that I’ve seen, but lots of other publications that follow the more common style—no comma—are still making “Donald Trump Jr.” possessive, which leads to a punctuation doublet:
Which again, is correct, but boy, is it ugly.
I know the news cycle is fast. If I wanted to be in the game, I should have posted this story yesterday. And sometimes you just have to get the story out, but for the love of all that is simple and clear, please spend 10 seconds trying to rewrite your headlines that are making “Donald Trump Jr.” possessive. The punctuation becomes distracting, and whether you get all the rules right or wrong isn’t the point. You don’t win a medal in the Copy Editing Olympics if your punctuation follows your house style but looks so weird people are thinking, “Ewww, what is that? Is that actually right?”
So, I respectfully suggest that copy editors get ahead of the problem by releasing an email to their writers. Show them ways they can rewrite these troublesome headlines because it looks like this guy might be in the news for a while.
“Donald Trump, Jr.,’s Love for Russian Dirt” can become “Why Donald Trump Jr. Loves Russian Dirt.”
“Donald Trump Jr.’s Free Speech Defense Is as Bogus as It Sounds” can become “The Bogus Free Speech Defense Won’t Save Donald Trump Jr.” And so on.
I’m sure there will be times when it’s too hard to come up with a good rewrite, but they’ll be rare.
And that’s your Quick and Dirty Tip: Editors, give your writers examples ahead of time to help them avoid the train wreck that is these double and triple punctuation marks on names that end in “Jr.”