Whenever I hear the expression "Free City" I think of two things (in no particular order). 1) I think of the Free City retail store on Highland Blvd in Hollywood that features tee-shirts, sweatpants, and hooded sweatshirts emblazoned with any number of catchy phrases and range in price from $100 to upwards of several hundred dollars. These items are great for uber-stylish hill-dwelling moms and dads with more money than sense who like to slum it with their strollers around Griffith Park in performative style- garbed in the bissonata of the apathetic chic. As silly as that is, I have to hand it to the designer - anyone who can get someone to spend $300 on what most people would wear to do their laundry is a genius.
Fernando Wood was a powerful Democratic Party politician and the mayor of New York City during the secession crisis. He was extremely troubled by the thought of the southern states seceding form the Union. Wood was opposed to the Republican Party platform and most particularly their stance against slavery - he believed, or at least argued, like many of his southern countrymen, that although Lincoln promised not to go after slavery where it already existed, it would only be a matter of time before abolition was the order of the day. But in the immediate sense, Wood was concerned with economic factors. New York City businesses did a great deal of trade with destinations south of the Mason-Dixon. Secession and war would mean an end to that trade...and of course, an end to many of Gotham's business interests. Wood proposed something of a secession movement himself - not to join the Confederacy per se, but to establish Manhattan as a free city, allied with neither side and open, as it were, for business with both. Wood had a number of supporters from the extreme faction of the Democratic Party but in the end New York Democrats thought he was pushing the issue too far. Wood's proposal was associated with treason and he was not reelected. Although he publicly hated Lincoln, Wood eventually (if grudgingly) supported the war effort once shot were fired - encouraging the formation of regiments, the raising of funds, and other war related activities.
So the next time I give a talk on New York City or Fernando Wood, I'll be sure to wear one of my Free City tee-shirts and see if anyone notices. And you can rest assured, I have enough sense not to pay hundreds of dollars for a tee-shirt. I got mine gratis. It pays to have connections, I suppose.