"to pull it off" was at one time used meaning "to win."
And in sentences such as,
I don't think you can pull it off.
, it often implies the idea of "success."
But how did this expression originate?
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Two immediate lexical progenitors produced transitive use of the colloquial phrasal verb 'to pull off' in the sense of
2. trans. colloq. To succeed in accomplishing, achieving, or producing (something); to carry off.
OED, 'to pull off'
Those two progenitors were uses in these senses:
a. To take away or detach (something) by pulling from where it is held or attached. ....
b. To take off (one's coat, etc.); to doff (one's hat).
Senses 1a and 1b are attested in OED from before 1425 (citation composed before 1399) and around 1500, respectively. Sense 2 is attested from 1860:
Baily's Monthly Mag. 1 34 After the good old matches of Club and Ground against Cambridge and against Oxford are pulled off at the two Universities, the London Season will open.
Although pulling off boots and coats, etc. (1b), often has a sudden, tangential element of success, it is likely that, at least in the US, transitional, figurative political uses played directly into the ready adoption of the sense denoting successful accomplishment, achievement or production.
A painstaking examination of primary sources — uses in the popular press — showed continuing dominance of sense 1b into the mid-1800s (lots of clothes were pulled off during that period), along with, much less frequent, uses in sense 1a (often with reference to pulling off parts of plants in articles concerning agriculture and gardening; sometimes with reference to pulling off flesh and skin).
The principal difference between senses 1 and 2 is relative materiality. Sense 1 takes tactile material as its object: boats, clothes, vegetation, flesh. The later sense 2 takes ideas or concepts as its object: a win, a success, an accomplishment, an achievement. Such chronological development of lexical sense is a standard process; it goes alongside the usually less-definable adoption of figurative senses.
Some transitional US uses, notably political, illustrate the development of the sense, from material things pulled off to immaterial, by way of figurative uses:
The Democratic Journals in New York have a mournful look. Fillmore, on one side, pulls on the anti Ostend conservative men, and Fremont, on the other, pulls off the Germans, Irish, &c., ....
The Wilmington Daily Herald (Wilmington, North Carolina), 18 Jul 1856.
Three times he has left governmental posts, ...after brave displays of political pluck; and now, for the fourth time he pulls off his cabinet cloak and throws it in the faces of his old fogy associates.
True American (Steubenville, Ohio) 08 Mar 1855.
These early, figurative US uses from 1855 and 1856 precede the earliest US use of 'pull off' in sense 2 found, from 1858:
His crowning success, however, was to pull off the two thousand guineas stake with Fitz Roland and the Derby with Beardsman.
The Brooklyn Daily Eagle (Brooklyn, New York) 05 Jun 1858.
As will be deduced from the currency of the stakes, if nothing else, that 1858 use, although it appears in a US newspaper, refers to an English horserace.
Setting aside the US transitional, figurative uses of 'pull off' in political contexts, and turning to UK uses, evidence of the development of transitive sense 2 appears earlier. In 1851, for example, rhetorically linked uses of the intransitive verbal phrase 'came off' and the transitive 'carry off' prepare for a third with the transitive 'pull [something] off'. The general subject is horse racing, and the direct object is an event:
The opening race across the flat came off in favour of the four-year-old Triennial winner...we suggested the probability of some undreamt of outsider carrying off the prize...[w]hether he has won or not, old Joe Rogers will delight in the accomplishment of the feat, for he...abhors pulling an event off with a favourite.
The Era (London) 19 October 1851
A slightly (four days) earlier use in scare quotes suggests the application of 'pull off' to the immaterial object of a horse-racing title is a neologism...at least as concerns the author of the piece and his judgement of Dublin readers' familiarity with the use of the phrase:
...and Mr. Quin's Whiff "pulling" off the First Class of Trainers' Stakes.
Freeman's Journal (Dublin) Wednesday 15 October 1851
Here again, in the UK, uses of 'pull off' in sense 2 are presaged by figurative uses in political contexts in sense 1b; such figurative use again involves the removal of articles of attire. One such, a very early instance, is this citation from the OED sense 1b attestations:
1677 W. Hubbard Narr. Troubles with Indians New-Eng. (new ed.) ii. 32 He pulled off his Vizour of a friend, and discovered what he was.
Another, contemporaneous with (although a few days earlier than) the 1851 uses in horse-racing contexts:
If the Roman Catholic Prelates...will come forward to denounce...the doings of Italian tyrants...we shal sing our palinodia with good will...[t]ill than, we shall continue to regard them as accomplices of the Emperor of Austria and Marshal Haynau...as so many MacHales and Cullens in disguise, waiting for the suitable moment to pull off the mask, draw the sword, and throw away the scabbard. — The Patriot
Belfast Mercury 02 October 1851
Figurative uses with reference to the pulling off of masks were thematic in the evidence I examined pertaining to sense 1b.
It may be objected to the foregoing account that a 'stake' is material: valuable goods or money wagered on the outcome of a bet, game, or event. So, then, uses of 'pull off' with, as direct object, the 'stake' wagered on a horse race, must at least be said to be figurative uses in sense 1a ("to take away" something "by pulling from where it is held"), rather than sense 2 ("to succeed at something" or "to win something").
However, the citations shown make clear that, where 'stake' or 'stakes' is used as the object of 'pulling off', it is being used in a specialized sense, and denotes the race (singular) or class of race (plural), rather than the material prize. The sense is OED sense 3a of stake, n.2:
pl. in Horse Racing, Coursing, etc., the sums of money staked or subscribed by the owners who enter horses or dogs for a contest, the whole to be received as the prize by the owner of the winner or divided among the owners of the animals ‘placed’, as declared in the conditions of the contest. Hence in sing. (cf. SWEEPSTAKE n.) a race for money thus staked or subscribed. Also in pl. with defining words as the designation of particular races or classes of races in which the sum of money staked is the prize as distinguished from a Plate (see PLATE n. 4), Cup, or the like.
(Bold emphasis mine.)
Thus, where the direct object of 'pull off' shown in the citations is not the "match" (1860, Bailey's Monthly Mag) or the "event" (1851, The Era), but rather "the two thousand guineas stake" (1858, The Brooklyn Daily Eagle) or the "First Class of Trainers' Stakes" (1851, Freemans Journal), the denotation of 'stake' is the race and the denotation of 'Stakes' is the class of race.
I found some slightly earlier uses than the OED's 1870. All are from the UK. The majority are from magazines. Nine are about horse-racing, two about rowing, and one each for football and coursing, and one using an analogy of being a good player, and the last about being lucky in general.
From the citations below, it seems fairly safe to say pull it off comes from horse-racing, and that it's usually the horse that pulls off, and the it is the name of the race or the prize -- the cup or the stakes. This then spread into other sports.
But why pull? This isn't entirely clear, but some definitions of pull relate to horses:
And conversely to the converse:
The 1863 Stable secrets: or, Puffy Doddles ; his sayings and sympathies by John Mills has four occurrences of "[the horse Sunshine would...] pull off the [event]":
(Plus a second almost identical passage in the next sentence.)
An 1865 edition of Fun magazine has the following in the "Sporting Intelligence" column, the first from 11th November mentioning the Liverpool Cup horse race:
The fact is, that a little seclusion will do me no harm, so shall lie by and try to pull it off over the Liverpool Cup.
And by the same writer and the same column on 17th June, a similar phrase when discussing horse races:
As for Ascot or the Ledger, you shall have them all in good time, and is much mistaken if I do not pull off both events as succesfully as Epsom.
An 1866 London Society magazine prints a small story called "Fast and Loose" that appears to be using it in an extended gaming analogy rather than directly.:
The game's well worth the winning; but he must be a beau joueur, indeed, who shall pull it off!' And then 'The Bey' had to take his share in the cross play of badinage and brilliant trifling it pleased Valerie to engage in.
An 1867 edition of The Eagle magazine by St. John's College, University of Cambridge has uses pulled it off in a sports report:
Yes, this is not rugby but football (US soccer), but Cambridge rules.
An 1867 edition of The Illustrated London magazine also uses it in a horse racing context:
To hear'them, one would not have the slightest doubt of their sanguine hopes of success.
"You told Challoner to hold him in till the finish, Powell," said Peep o' Day's owner.
"Ay, ay, my Lord; never fear!" chuckled the astute old trainer: "We have made that ere little business all right, and last night as ever was, a small chap we had got to watch Athleta taking his gallop, said that he was short in the stride, and looked pumped at the end of it. We shall pull it off, my Lord, safe as houses."
An 1866 The Suburban Magazine describes a rowing race victory:
rowing all the four-mile distaince with their bow close to our No. 2's oar ; and only by the sheer pluck of our crew, pulled it off. They earned us about, the ZRC, on their shoulders after the race, filling the air with their shouts. Ah, it was a glorious time !
Tony Pastor's Book of Six Hundred Comic Songs and Speeches (1867) is used when betting at the races:
An 1868 Baily's Magazine of sports and pastimes has two occurrences of a horse or jockey "to pull off the cup":
Some more from 1869:
The book Harry Egerton; or, The Younger Son of the Day by George Charles L. Tottenham, discusses horse racing.
Two uses of pull it off in The Sportsman magazine, one about coursing (racing greyhounds chasing hares) and the other about horse-racing.
The Tomahawk magazine, discussing the Oxford-Cambridge boat race.
Again Baily's magazine of sports and pastimes, discussing a horse race.
And a non-sporting use in the 1869 A London Romance by Charles H. Ross:
“I didn't say that,” retorted Frank; “I've made a bit of money now and again. One is not always lucky. I don't complain; I shall pull it off yet. I don't want any one's help or sympathy. I'm quite capable of fighting my own battles.
I have not been able to find any explanation of the origin of the phrase "pull [something] off" beyond the sketchy one that Robusto cites in his answer. For completeness, I give the full entry from Eric Partridge, A Dictionary of Slang and Unconventional English, second edition (1938):
pull off. To obtain (some benefit) : sporting : 1870 (O.E.D.). Ex sporting j[argon], to win.—2. Hence, to succeed with, or in effecting, something : 1887, Black, 'We haven't pulled it off this time, mother.' O.E.D.
Although Partridge doesn't narrow the source of "pull off" beyond "sporting," Hugo in his answer suggests that the source was probably horse racing, backing up his hypothesis with an earliest instance of the phrase from 1863, where the context is indeed horse racing.
I found four examples from 1860 and the first part of 1861—two from horse racing and two from prize fighting. All four instances are overseas reports of happenings on the turf or in the ring in England, so it may well be that a search of British newspapers would yield even earlier matches for "pull it off" in the relevant sense.
Now let's look at the earliest four 1860 and 1861 matches for the phrase. First, from "The British Turf: Ascot Races," in the New York Clipper (June 30, 1860):
The Ascot Stakes, on which the betting was neither brisk nor heavy, followed the Two-year-old Biennial, and fifteen [horses] went to the post. This proved a capital turn for the book-makers. Mouravieff, who won a beautiful race by a head, was scarcely backed for a shilling, although his nominal price in the betting was 12 to 1[.] Having won a race of two miles two hours previously, he was not expected to do the trick again : however, the stake was worth trying for, and he pulled it off[.] The Ascot Derby was a gentle exercise for the Wizard; and then seventeen of all ages went to the T. Y. C. post for the Queen's Stand Plate—a new item on the Ascot bill of fare, worth £640 to the inner.
From "Epitome of English Sporting," in the Bell's Life in Sydney [New South Wales] and Sporting Reviewer (July 14, 1860):
In the Oaks Betting the One Thousand winner had not taken the lead, but was content with third or fourth place on the list[.] John Scott, however, has always been a very dangerous customer in the "Ladies' Race," and has often pulled it off quite against public opinion.
From "Sports Abroad: The Ring: Fights to Come," in the New York Clipper (September 22, 1860), originally in the London Sporting Life (August 29):
[October] 18.—Bob Brettle, of Birmingham, and Jem Mace, of Norwich, £200 a side—home circuit.
THE COMING GREAT FIGHT BETWEEN BRETTLE AND MACE. A further instalment of £15 a side in this interesting match is to be made good at Mr. W. Richardson's, Blue Anchor, Shoreditch, on Friday next. On Monday, Brettle took a sweat from his training quarters and visited Lichfield for the races, in company with Joe Wareham, who is training both him and Young Bodger Crutchley. Bob was in good condition, and his friends offered to lay £50 to £40. One gentleman has got on a cool hundred at evens. ... Mace is taking his breathings by the seaside, under the care of Alfred Milner, of Sheffield, and his old trainer "Friday," or Norwich. Mace, it appears, likes the match, and says he can pull it off to a certainty.
From "Latest Sports in London," in the New York Clipper (April 6, 1861):
There have been, during the past week, several good little mills, but as I was away at the Liverpool gathering, I can only speak from hearsay. ... Ruff of Nottingham and Curley of Sheffield, also had a slashing affair, which lasted one hour and 28 minutes, and in which 55 rounds were hotly contested; Ruff's friends seeing that he then had no chance of pulling it off in his favor, wisely threw in the sponge in token of defeat, and Curley was declared the victor. Millington and Bagot, also went through their performance for the mastership, and £40, which neither succeeded in pulling off, on account of a disturbance, and the ring being broken in, when the referee at once declined to act any longer, and the men agreed, after having fought 65 rounds in 92 minutes, to draw stakes, and thus the matter rests. It will be seen that there has been plenty of boxing for those fond of it.
Although the meaning of "pull it off" in these various instances clearly tends toward the simple idea of "win," as Partridge indicates, I suspect that the literal focus of the "pulling off" is the stakes—the prize money. Mouravieff tried for the stake at Ascot and pulled it off. Mace wants to pull the £200 betting stake from his opponent off the table. Neither Millington nor Bagot succeeded in pulling off the £40 prize, so they had to "draw stakes" instead. (It seems clear that the term draw derives from a situation where competing fighters reach a stalemate without a winner, in which case the two sides' bettors must withdraw the stake they put up without pulling off the other side's stake with it.)
If I am right that the "it" in the phrase "pull it off" originally referred to "the stake," you would expect to find mentions of the phrase "pull the stake off" or "pull off the stake" in at least a few early sporting accounts. An Elephind search does uncover a number of such instances from the 1860s, all in connection with horse racing. The earliest of these is from "Randwick Autumn Meeting," in the [Sydney, New South Wales] Empire (May 6, 1861):
As Johnny Cutts pleased, so he won. The next was another certainty, young Battye bringing Peter Possum first past the chair without any trouble. Then came the Champagne, for which The Nun was the favourite; but Mr. De Mestre's luck was in, and Exeter pulled off the stake, Holmes beating the favourite for second place. The Three-mile Handicap brought six to the post, and Talleyrand won pretty easily, old Veno, with all the weights, being second.
Likewise, from "New South Wales for the Melbourne Cup," in the Bell's Life in Sydney [New South Wales] (June 23, 1866):
I am not fond of three-yr-olds in big handicaps at the beginning of the season; but if there is really a good one among these, and well on the day, he or she may pull the stake off in such a field, for a more unaccountable one I never tried to make anything out of. Report says that Maribyrnong is to be the nag of Mr Fisher's stable; but from among three such as Budelight, Sea Gull, and Maribyrnong, it is not easy to say which will be the pick.
And from "Intercolonial News: Victoria," in the Sydney [New South Wales] Morning Herald (April 4,, 1867):
Mr. Goyder, the well-known turf vates and bookmaker, was summoned on Friday in the County Court by a chemist named Ready, residing at Maryborough, for £50 damages, on account of an assault committed upon the Melbourne Racecourse. Ready cme to town to see the last Champion Meeting, and on arriving at the course, he patronised the betting ring, with the intention of "potting" on The Barb. Here he fell in with Mr. Coker, and accepted that gentleman's offer of 20 to 8, in sovereigns, against his favourite horse. When The Barb had pulled off the stake, and Mr. Coker was about to pay tho £20 to Ready, Mr. Goyder interfered and prevented him from doing so by saying that Ready owed him £5. The latter gave the statement a flat denial, and Goyder knocked him down. Mr. Coker paid him next morning, but he brought this action against Goyder for the injury and unwarranted exposure he had received, as, although he did owe him £5 on account of a bet at Ballarat, he sent a cheque for the amount shortly after the debt was incurred. Mr. Goyder, however, said that he never received the £5, and that the alleged assault lay in an attempt which he made to pull the nose of Mr. Ready, who frustrated his intention by falling over backwards. His Honor Judge Pohlman found for the plaintiff, with £25 damages.
Additional instances of the wording appear from 1867 through the 1870s (at least).
Realistically, the expression "pull it off" is already figurative in the earliest matches (from 1860) cited here, but the vestige of a literal pulling off of the wagered stakes remains dimly visible.