Should you capitalize 'city' in 'city of Boston'?

Does your Bostonian friend hail from the City of Boston or the city of Boston?

Before you answer, here’s a hint: It depends who’s asking.

I flunked this question on an editing quiz recently. I got it wrong even though I’ve spent decades — literal decades — getting paid to change City of Los Angeles to city of Los Angeles and City of Pasadena to city of Pasadena.

So what happened? I was editing according to Associated Press Stylebook rules and the quiz was in Chicago Manual of Style rules.

In AP style, which is followed by many news media and business organizations, the c is lowercase. I like that. After all, “city” isn’t part of the name. If you live in Boston, you don’t write City of Boston on the top left hand corner of envelopes when you send mail. The city name is Boston, period. But the Chicago Manual of Style, which is followed by book and magazine publishers, disagrees. If you’re following their style, City of Boston can be the way to go.

Clearly, capitalization can be confusing — especially if you take your cues from your reading material. Here's my recent column explaining how to navigate these questions.

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