Was "Yankee" originally a derisive term for smugglers?

Question

Johan Norberg in Open: The Story of Human Progress (2020) claims:

‘Yankee’, after all, was originally a derisive term for smugglers.

Is this true?

Answer 1

It's not as certain as Pete's answer makes it. Wikipedia's take, just on the Dutch angle:

Most linguists look to Dutch language sources, noting the extensive interaction between the Dutch colonists in New Netherland (now largely New York, New Jersey, Delaware, and western Connecticut) and the English colonists in New England (Massachusetts, Rhode Island, and eastern Connecticut).[8] The exact application, however, is uncertain; some scholars suggest that it was a term used in derision of the Dutch colonists, others that it was derisive of the English colonists.

Michael Quinion and Patrick Hanks argue that the term comes from the Dutch name Janneke, a diminutive form of Jan (John)[13] which would be Anglicized as "Yankee" due to the Dutch pronunciation of J as the English Y. Quinion and Hanks posit that it was "used as a nickname for a Dutch-speaking American in colonial times" and could have grown to include non-Dutch colonists, as well.[13] The Oxford English Dictionary calls this theory "perhaps the most plausible".

Alternatively, the Dutch given names Jan (Dutch: [jɑn]) and Kees (Dutch: [keːs]) have long been common, and the two are sometimes combined into a single name (e.g., Jan Kees de Jager). Its Anglicized spelling Yankee could, in this way, have been used to mock Dutch colonists. The chosen name Jan Kees may have been partly inspired by a dialectal rendition of Jan Kaas ("John Cheese"), the generic nickname that Southern Dutch used for Dutch people living in the North.[14]

The Online Etymology Dictionary gives its origin as around 1683, when English colonists used it insultingly in reference to Dutch colonists (especially freebooters). Linguist Jan de Vries notes that there was mention of a pirate named Dutch Yanky in the 17th century.[15] The Life and Adventures of Sir Launcelot Greaves (1760) contains the passage, "Haul forward thy chair again, take thy berth, and proceed with thy story in a direct course, without yawing like a Dutch yanky."[16] According to this theory, Dutch settlers of New Amsterdam started using the term against the English colonists of neighboring Connecticut.[14]

So it's not really a consensus among etymologists that "Yankee" originally meant smuggler (and more properly pirate perhaps, in that view), although it is one theory with some backing.

Answer 2

The claim being made is basically false because the etymology of yankee is not certain to anyone. These are the three strongest arguments I see:

1/3: It originated from an unknown African language, arriving by 1725

Wikipedia quotes the earliest English usage as 1758, but this is not true. The earliest usage with the exact spelling "Yankee" apparently dates to 1725.

The inventory of the effects of William Marr, formerly of Morpeth, and afterward "of Carolina, in parts beyond the seas, but in the parish of St. Dunstan, Stepney" (1725) ends with, "Item one negroe man named Yankee to be sold." Mr. W. Woodman, of Morpeth, has the document.

J. T. F., in Notes and Queries, 5th series (1878), vol. 10, p. 467

This document is still available in the Northumberland Archives, which states that William Marr lived in Charleston, South Carolina. This is in accord with a 1765 commentary claiming that the term originated in the South. Why exactly this slave was named Yankee is unclear and may relate to the second etymology below, or perhaps this slave kept his African name.

While checking to see if I might find the name "Yankee" in other records, I learned the rather dismal fact that the names of slaves were rarely written down before 1800, except in newspaper runaway slave notices.

2/3: It originated from a student slang word for "a slow person" in 1713/1728

This is attested in a 1788 publication, by which time the origin of the word was already unclear.

You may wiſh to know the origin of the term Yankee. Take the beſt account of it which your friend can procure. It was a cant, favorite word with farmer Jonathan Haſtings of Cambridge, about 1713. Two aged miniſters, who were at the college in that town, have told me, they remembered it to have been then in uſe among the ſtudents, but had no recollection of it before that period.

The inventor uſed it to expreſs excellency. A Yankee good horſe, or Yankee cider and the like, were an excellent good horſe and excellent cider. The ſtudents uſed to hire horſes of him; their intercourſe with him, and his uſe of the term upon all occaſions, led them to adopt it, and they gave him the name of Yankee Jon. He was a worthy honeſt man, but no conjurer. This could not eſcape the notice of the collegiates. Yankee probably became a by-word among them to expreſs a weak, ſimple, awkward perſon; was carried from the college with them when they left it, and was in that way circulated and eſtabliſhed through the country (as was the caſe in reſpect to Hobſon's choice, by the ſtudents at Cambridge in Old England) till from its currency in New England, it was at length taken up and unjuſtly applied to the New Englanders in common, as a term of reproach.

William Gordon, The history of the rise, progress, and establishment, of the independence of the United States of America, including an account of the late war, and of the thirteen colonies, from their origin to that period (London, first edition, 1788), vol. 1, p. 482.

This is a very good story because this use of Yankee is already close to how it is used in "Yankee Doodle." We have no other verification of the 1713 date, but another source attests to a written document dating to 1728:

One of theſe letters, dated "Cambridge. Sept 27, 1728," the editor has before him. It is a moſt humourous narrative of the fate of a gooſe roaſted at "Yankey Haſtings's" and it concluds [sic] with a poem on the occaſion, in the mock heroic.

"Certificate respecting the Rev. John Seccombe," Massachusetts Magazine, vol. 7, no. 5 (August 1795), pp. 301-302. (I here interject that John Seccombe, the author of this letter, would have been 80 years old in 1788, and thereby an "aged minister." He graduated Harvard in 1728.)

If we accept the early date of 1713, and the story of "Yankee" being distributed throughout the country as a witty piece of slang, then the slave named Yankee in 1725 might have been given the name as an insult. (Although, posthumously, a rather prestigious insult, as he became the first recorded Yankee in history.) However, if we don't accept the 1713 date, then the name might have traveled northward from the South.

3/3: It originated from a Dutch diminutive for "sailor," dates unknown

The problem with this theory is that we have no evidence of a Dutch speaker calling a non-Dutch speaker a yankee/jantje. But unlike the other two derivations, in this case jantje was a generic term with a maritime connection that might have brought it to the attention of sailors in the Royal Navy.

Most relevant for our problem, however, is the existence of Jan and jantje as absolute nouns, and with the meaning of "een matroos, inzonderheid: matroos van een oorlogsschip; thans nog zeer gewoon als benaming van de matrozen der Kon. Nederl. Marine" (WNT VII, s.v. Jan col. 191). That is 'seaman, navy soldier, in particular crew member of a warship, currently still very common as name of the sailors of the Royal Dutch Navy.' So that both in speaking and in writing one can have, for example, onze jantjes meaning 'the boys of our Navy, of our fleet' and the like. There is, in other words, absolutely no need to find Dutch ships or Dutch captains called Yanky, since the general meaning of jantje provides a sufficient, and indeed much stronger, piece of evidence for the etymology.

Mario Alinei, "Yankee: A Dutch Etymology Revisited," Language in Time and Space: Studies in Honour of Wolfgang Viereck on the Occasion of his 60th Birthday (Franz Steiner Verlag, 1997)

This is the etymology being referred to in the question and by other answers, but it lacks for any sort of contemporary written evidence, so we certainly cannot arrive at the conclusion that Yankee originates from freebooter.

Answer 3

From Etymology Online :

Yankee (n.)

1683, a name applied disparagingly by Dutch settlers in New Amsterdam (New York) to English colonists in neighboring Connecticut. ... Originally it seems to have been applied insultingly to the Dutch, especially freebooters, before they turned around and slapped it on the English.

From Dictionary.com

Freebooter

a person who goes about in search of plunder; pirate; buccaneer.

So, basically, more or less true. Pirates rather than smugglers, but it's possible it was applied to smugglers too.