Early instances of 'booby-prize' and 'boobie' (or 'booby') in Scotland
The earliest match I've been able to find for "booby prize" comes from Ascott Hope, Dumps: A Tale of the Tawse, serialized in Young England (September 1884):
We go out of school early after receiving final directions as to the examination. There was one other ceremony of a less public kind than that to be performed next day. At the end of every session the dominie [schoolmaster] had the satirical custom of presenting his tawse ["A leather whip divided at the end into strips, formerly used to punish children," according to The American Heritage Dictionary of the English Language, fifth edition (2011)] as a "booby-prize" to some idle or stupid lout whom he picked out as meriting this distinction, so that next time they met he might start fresh and fair with a new pair for a new set of classes. Usually there was a great deal of fun over the business ; but on th present occasion it seemed like to pass off rather seriously. The dominie, holding up the old tawse, asked—
"What are we to do wi' these noo? Shall we gie them to Tam Rutherford? As he's gotten his licks for takin' them, he might as weel hae them, then he canna say it was a' for naething."
"Ascott Hope" was a pen name of Ascott Robert Hope Moncrieff, who was born and raised in Perth, Scotland. The antecedent for the term seems to have been the idea of "sitting booby [or boobie]," as we see in this instance from Lord Henry Cockburn, Memorials of His Time (1840/1856), describing his experiences in what was then called "high school" in Edinburgh, which he attended from 1787 to 1791, beginning as an eight-year-old:
Out of the whole four years of my attendance there were probably not ten days in which I wad not flogged, at least once. Yet I never entered the class, nor left it, without feeling perfectly qualified, both in ability and preparation, for its whole business ; which, being confined to Latin alone, and in necessarily short tasks, since every one of the boys had to rhyme over the same words, in the very same way, was no great feat. But I was driven stupid. Oh! the bodily and mental wearisomeness of sitting six hours a-day, staring idly at a page, without motion and without thought, and trembling at the gradual approach of the merciless giant. I never got a single prize, and once sat boobie at the annual public examination. The beauty of no Roman word, or thought, or action ever occurred to me ; nor did I ever fancy that Latin was of any use except to torture boys.
The term boobie for 'person at the bottom of his class" also appears in a collection of essays written between 1830 and 1846 by Robert Chambers and republished, in Edinburgh, in 1846. Fromm "Booby" in Chambers' Essays, Familiar and Humorous (1846):
In most well-conducted academies, there is no situation which combines so much distinction with so much comfort as that of Booby. At the top there is distinction, but no comfort. What with the questions put by the master to make a show before strangers, and what with those put by the inferior boys who want to displace him, Mr. Dux is a most unenviable victim of ambition. Commend me to that equally conspicuous and much more agreeable situation, where one is surprised by a question or taken to task on an exercise perhaps once in the twelvemonth, but left during all the rest of the time to self-enjoying reflection or amusement ; I mean the situation of Booby. There, far below the reach of the storms which agitate the surface, alike unobserving and unobserved, you spend that very life of perfect ease and content which the classic poets you are supposed to be studying so strenuously recommend. In fact, so far as practice shows, Booby may be said to study the classics to more advantage than any of his companions. No man so thoroughly obeys the Horatian maxim 'Equam memento,' as he. No man shows more of the true spirit of the stoic. The uneasy honours of Dix he regards with more cool contempt than ever Diogenes expressed for the lustrous fame of Alexander. Mr Booby, indeed, enjoys a philosophical tranquillity such as the ancients, with all their affectation of a love of lowly ease, never dreamt of. It is the tranquillity not only of situation, but of a mind at ease with itself and with all around it. There is no self-seeking in the heart of Booby. His excellent friend, Second Booby, has sat by his side for years, and never yet has he formed the wish to degrade him from a place which he seems so well fitted to enjoy and adorn.There may be treachery in a friendship between Fifth Dux and Sixth Dux ; but in Booby there is 'a faith that knows no guile.'
Evidently, then, the boys in at least some high schools were arranged like the violinists in an orchestra, with the most accomplished individuals sitting at the front and the least at the back. The meaning of "sitting boobie" immediately becomes clear.
Early instances of 'booby prize' in the U.S.
Whether it arrived from Scotland or arose coincidentally and independently, the expression "booby prize" seems to have spread in North America through an odd medium: the game of progressive euchre. From a letter by Lucy Leggett published in the Pontiac [Michigan] Gazette (January 30, 1865):
Progressive euchre is not altogether a new game but a curious romping arrangement of the old, in which three tables are numbered, one, two and three, and cards similarly marked are drawn for partners. The first table plays for games, the second and third for points; the last table is called the “booby” table. When a game is won at the first table the bell rings, and the defeated parties move down to the booby table, changing partners; while the parties who have the most points at that table move up to the second and those at the second to the first. Three prizes are given, one for the greatest number of games, one for the most points, and one for the least, this is called the "booby” prize. The points are called by an umpire at the end of each game, and the sum total decides to whom the prizes shall be given.
From "Local" in the Cheboygan [Michigan] Democrat (February 19, 1885):
At a recent progressive euchre party the booby prize was a live mouse in a box. It was won' by a lady and there were eleven other ladies in the room. It is an act of charity to draw the curtain o most that followed the discovery of the mouse, but as a business matter it should be said that the furniture can be made good for about $27.
From "More Progressive Euchre," in the Springfield [Ohio] Globe=Republic (March 25, 1885):
A progressive euchre party was given last night at the residence of A. Q. Chase, on Kizer street, in honor of his guest, Miss Haman. ... The game began about 8 o'clock, and lasted several hours. It resulted in Miss Jefferies win the high ladies' prize, Miss Hainan the low or booby prize, and Mrs. Ward Frey the progressive prize. Among the gentleman, George Rawlins gained the high gentleman's prize, Frank Hosterman the booby, and Will Donnell the progressive. Alter the game was concluded the company partook of refreshments, which were simply perfection itself, and finally dispersed about 1 a. m.
From "Pithy Paragraphs," in the Burlington [Vermont] Weekly Free Press (March 7, 1885), reprinted from the Chicago [Illinois] Tribune:
Roller skating at best is a craze and is no worse than other crazes, such as tobogganing, bobbing, progressive euchre, four o'clock teas, metaphysical seances and other mild forms of insanity, at which all that i charged against roller skating may be committed. Has it never occurred to thee moralists, who, we fear, have passed the heyday of youth, that the toboggan offers facilities for flirtation, and that in the wild and reckless struggle for the booby prize in progressive euchre many a young man may be sowing the seeds of progressive poker? If the young persons can not be trusted in the roller skating rinks, can he or she be trusted anywhere else?
And from Mary Jane, "Booby Prizes," in the Salt Lake City [Utah] Herald (May 10, 1885):
I am one of those who have fallen a prey to the reigning topic—progressive euchre, and I observe with interest all that pertains to the popular game. I would like to say, however, that a good many young couples in their desires, perhaps to go just a little ahead of their neighbors, have lately inaugurated a practice of spending more money on the prizes than is really needful. I refer to the custom of providing "Booby" prizes of a character just as elegant as the leading prizes. What nonsense this is! Where is the glory of coming out at the head if the foot meets with an equal reward, and what becomes of the signification "Booby," unless the foot prizes are something of a nature to suggest this name? I have noticed lately a good many who seem as anxious to obtain the booby prize as others are the first prize.
Sam Jones, "The Righteous and the Wicked," published in Sam Jones' Own Book: A Series of Sermons (1886) takes up the issue of gambling in progressive euchre:
There's many a starved mind in this country, brethren. If I were simply to feed my body upon husks with no nutriment, how could I perpetuate physical life? If I do not sit down and eat those things that tend to produce strength and perpetuate life, in so far am I sinning against my body. I wonder hat those people are doing that spend their intellectual hours playing cards? How much mental food is there in that? One evening, where I was preaching, I denounced social card-playing and progressive euchre. Lt me tell you. too, if you play progressive euchre—and I don't care whose son, whose wife, whose husband you are—you are a gambler as much as any blackleg in this city. You can't play progressive euchre without the "Booby prize," and you can't play for a Booby prize without putting up the stakes ; and if you win or lose, you are a gambler in the sight of God just as much as is the worst black leg that ever cursed this city.
Although Jones began his career as an evangelist in Georgia, he reported in an autobiographical preface to his book that since January 1883 he had preached in Brooklyn, New York; St. Louis and St. Joseph, Missouri; Cincinnati, Ohio; Chicago, Illinois; Baltimore, Maryland; Washington, D.C., Indianapolis, Indiana; Waco, Texas; Mobile, Alabama; and Nashville and Knoxville, Tennessee. That's half the original major leagues and a good bit of the American Association to boot. Newspaper mentions of Jones's hostility to progressive euchre go back to at least May 13, 1885 (in "A Southern Revivalist: Some of Sam Jones's Sayings in His Public Addresses," in the Indianapolis [Indiana] Journal).
By the end of 1886, Americans were awarding booby prizes to individuals outside the realm of progressive euchre. From Della Greenleaf, "Bloomfield [Iowa] Chapter" in The Arrow: Official Organ of I. C. Sorosis Pi Beta Phi (December 1886):
We have had two "grub suppers" this fall, and gave an "apron social" also. This was quite an enjoyable affair. We I. C.'s all wore unhemmed aprons tied around the waist with ribbon, a piece of which had been previously cut off and sealed in an envelope. At the proer time the envelopes were passed, and the gentlemen present were requested to take the ribbons from the envelopes, find the aprons to match and hem them. Then came the time when "laughter reigned among the girls, awkwardness among the boys, and merriment over all." Two prizes were given when the work was finished—"grand prize" to the best, and "booby prize" to the poorest hemmer.
A more detailed account of this party activity—including the interesting fact that the young women continue to wear their unhemmed aprons while the young men attempt to hem them—is described in "Hemming Aprons," in the [San Rafael, California] Marin County Journal (November 4, 1886), reprinted from the Chicago Tribune:
In addition to the quotation party, which may take the place of progressive euchre this winter to a large extent, there is another novelty which bids fair to be popular. It is styled the "rainbow" party and takes its name from the bright hues of the ribbons which play an important part. ...
... Probably out of the whole number [of young men] there will be not more than one or two who go at the work with anything like method or skill, and even their efforts are so nearly on a par with the little girl taking her first lesson that the exhibition is usually more amusing than the out-and-out awkwardness of the others. When all are done the aprons are handed to the judges for inspection, and after their decision the prizes are awarded. Matchsafes, scarfpins, etc. are the proper thing for the first and second prizes, while the booby prize is usually a treatise on embroidery or something equally interesting to the masculine mind. A* souvenirs of the occasion the ladies keep their aprons and the gentlemen their thimbles.
I don't think Sam Jones would approve of this form of amusement either. In fact, he would probably would condemn the practice of awarding booby prizes for the worst attempt by a contestant in a game of pin the tail on the donkey, as described in "Local Lore," in the Cheboygan [Michigan] Democrat (December 30, 1886):
Donkey parties promise to become popular below his winter. They are not confined to juveniles, as one might suppose, but are enjoyed by the older folks. ... The [blindfolded] person who makes the best effort to place the tail upon the donkey where it belongs, receives a present of some kind, while the guest who makes the most unsuccessful effort gets the booby prize.
The Scottish tradition of calling the lowest-ranked student in a class "boobie" led in at least one published instance (in 1884) of a teacher awarding, at the end of the school term, a "booby-prize" of his worn-out implement of punishment to a supposedly deserving student.
I did not find any allusions to the Scottish schoolboy "boobie" in the flood of instances of "booby prize" that began in 1885. It is certainly possible that the instance of "booby-prize" in the serialized Scottish novel Dumps in 1884 was a solitary occurrence that had no connection to the U.S. usage related to the card game of progressive euchre that emerged a year later. The jump in usage, if it occurred, is not merely from Scotland to the United States, but from Edinburgh to the U.S. Midwest—Michigan, Ohio, and Illinois—after which it quickly radiated throughout the country. By the fall of 1886, "booby prizes" were being awarded in party games unrelated to euchre.
And by 1890, "booby prize" was beginning to appear in print in a figurative sense—that is, in situations where no actual award for poor performance was being offered. For example from "A Game of the Senses," in Michigan School Moderator (November 6, 1890), reprinted from Wide Awake:
The new methods of education are taking care of eyes and hands used together, but what classes are there for your nose, your ears, your touch, your sense of weight? Where do you go to school to learn to see in the dark, to smell fire, to hear flies sneeze? You can train your senses every minute you are awake. At this moment what do you see, hear, smell? Are you sure you really see, hear, and smell what you think you do? Suppose you make a game of "The Senses," and see how many come nearer the booby prize than the first one.
And from "German Authority on American Investigators," in Western Medical Reporter (February 1891):
Cultures were sent by both doctors [Billings and Salmon] to Dr. Koch, and with the many published bulletins, pro and con, were referred to Dr. Frosch, who had just published his conclusions, which seem to be the reverse of those reached by our own dear old Bureau of Animal Industry ; insomuch so that he says Dr. Billings is right, and says further that Dr. Salmon stocked the cards when he fixed up his commission to go out upon their bacteriological investigations. He declares that the investigations made by Billings were necessary to correct the discrepancies of Dr. Salmon, awards the latter the booby prize and warns him to go and sin no more.