The Massachusetts 1776 Pine Tree Copper Penny was virtually unknown until a grocer discovered this unique pattern piece while excavating near Hull or Charter Street in Boston's North End. Boston collector Jeremiah Colburn acquired the coin about 1852 and several years later published an account of it in The Historical Magazine, although he erroneously described the Liberty as "holding in her right hand an olive leaf." (Footnote 1) In the same article Colburn mentioned a "Janus Head" halfpenny in the collection of Matthew A. Stickney and attributed the dies for both coins to Paul Revere on the basis that there were few engravers in the colonies capable of such work. After revising his article, Colburn sent it to several newspapers in 1858, but he neglected to correct his description. (Footnote 2) Montroville Dickeson included the Pine Tree Copper in his Numismatic Manual in 1859, (Footnote 3) apparently using the Historical Magazine as his source, because Liberty was still described as clasping an olive leaf. The coin next appeared when John K. Curtis advertised "the unique Massachusetts Copper Coin" in a sale to begin February 1861. (Footnote 4) It was back on the market by December 1, 1862, when W. Elliot Woodward announced that he would be offering "the unique Pine Tree Copper, from the collection of Mr. Colburn, illustrated in Dickeson's Manual" at an 1863 sale. (Footnote 5) Boston numismatist William Sumner Appleton (1840—1903) added the coin to his collection of American coins and medals.

Appleton also wrote about the coin, adding the information that it was one of two pieces prepared in 1776 as patterns for a proposed Massachusetts state copper coinage. (Footnote 6) While there is no mention of such a proposal in the Acts and Resolves of Massachusetts from 1775 through 1778, Appleton deduced that the existence of a 1776 state copper coinage in New Hampshire made it a viable assumption. Appleton correctly described the goddess holding a Liberty-cap atop her pole; but he misread the "d" as "c" in the obverse legend flanking the tree (1d LM), which he interpreted as "one cent lawful money." (Footnote 7) Five years later, in 1875, Sylvester S. Crosby published his monumental work on early American coins, using a line drawing of the Pine Tree copper which incorporated this error, yet the book's heliotype reproduction of a cast from the coin clearly shows the "d." (Footnote 8) Crosby also linked the Pine Tree penny and the "Janus Head," more appropriately named the "Massachusetts Halfpenny." Half the size of the penny, the halfpenny features a reverse which is almost a mirror image of the Pine Tree. (Footnote 9) Still in the Stickney collection in 1875 and now in a private collection, the halfpenny had been discovered with an engraving and proofs of Revere's continental currency notes, so Stickney attributed the coin to Revere. (Footnote 10) The 1776 penny and halfpenny share a primitive vigor and design and are clearly the work of one person. Recent scholarship comparing lettering details with Revere's engraved 1775—1776 currency and securities printing plates confirms that Revere was the designer and engraver of both coins. A Massachusetts state 1776 copper coinage never materialized, probably due to the shortage of copper, so the two coins are considered pattern pieces and are unique as such. (Footnote 11)

Revere's design for the Pine Tree Penny borrowed symbols from local and classical sources. The pine tree alludes to both the Sons of Liberty flag from the Revolutionary era and to the earlier colonial pine tree coinage, representing Massachusetts's determination to govern herself. (Footnote 12) The goddess of Liberty, freely adapted from the Britannia of English coinage, (Footnote 13) holds aloft the Pileus cap, a symbol since the Roman Empire of a slave's manumission. (Footnote 14) The animal at her feet is a watchdog, vigilant in the service of its mistress. (Footnote 15) All of these elements combine to create such an attractive coin, that several different copies have been made of the piece. None is from a cast of the coin, and most mistakenly have "I C LM" flanking the tree trunk. This leads to the conclusion that they were made using Crosby's 1875 line drawing as a model. Of the magnificent collection of American medals and coins which William Sumner Appleton bequeathed to the Society in 1905, the Massachusetts Pine Tree Copper Penny remains the most requested research piece.