Cleaned out in the sense of ‘no money after (gambling) losses’ first appears in an American edition of a play performed at Covent Garden that same year:
Tyke. So what with that and playing cards … I was —
Lord Avon. Ruined.
Tyke. Yes; as Jockey Lords said — completely cleaned out. — Thomas Morton, The School of Reform (comedy), Philadelphia, 1805.
It may be obvious to point out that an idiom send/take to the cleaners with a quite similar meaning requires 1) people referred to as cleaners and by metonymy, their workplace, and 2) customers who had textiles to send there.
The first condition is satisfied by shops that specialized in textile cleaning beyond the shirts and heavy cottons either washed at home or sent to laundries: woolen suits, furs, leathergoods, silk dresses, rugs and carpets, curtains, etc. The second condition is met by a growing urban middle class whose household, at least until World War I, might have included one or two servants, but who needed to send large or more delicate items to professional cleaners. As the 20th c. progressed, this would increasingly include dry cleaning, or “French cleaning,” as it was initially called, after the country where it was first patented:
New York Tribune, 21 Apr.1883.
Between you and me, I should not wish to inquire how long a fashionable girl will wear a five-dollar French corset without sending it to the cleaners, for washing, you know, spoils its perfect set, and French cleaning is expensive. — Indianapolis Journal, 19 May 1889.
In case you’re wondering, $5 in 1889 was worth $136 in 2018 dollars. With the New York dyer now offering French cleaning and the fashionable woman wondering how to clean a corset, the stage is set for metaphoric extensions of sent/taken to the cleaners.
To the Cleaners (Sports)
The first metaphoric sense of send/take to the cleaners sprouted in that always fertile soil of colorful metaphors: sports reporting for daily newspapers. At this point, however, it isn’t about losing money, but simply losing:
When the bill [permitting prize fights in Nevada] became a law, he set about arranging a match between Corbett and Fitzsimmons, and as Jim had taken a change of heart regarding his renouncing of the game, which he did on the night after Maher sent O’Donnell to the cleaners in jig time …— Salt Lake Herald, 10 June 1906.
Both O‘Keefe and Tibbitts, the main event performers, seemed out of condition and it did not take long, to show that lack of form was the principal feature of the contest. O‘Keefe showed whatever skill or class there was, but Tibbitts was strong and aggressive, especially in the earlier rounds, and on several occasions he had O‘Keefe ready to be sent to the cleaners. — San Francisco Call, 16 Mar. 1910.
Eddie is a pugnacious sort of a chap all right, and down in California has sent more than one ragged ball player to the cleaners. Tacoma Times (WA), 24 Apr. 1911
And there were hundreds of other bouts in which ambitious youths were sent to the cleaners in a space of time that was alarming. — Bisbee Daily Review, 21 Jan. 1912.
Case was second to Nicholson of Missouri, last year at the games, but since that time has taken “Nick” to the cleaners on several occasions. — Urbana Daily Courier, 16 April 1913.
So many athletes and teams were sent/taken to the cleaners in the years since the expression emerged that it made a 1913 list of synonyms for lose:
To Lose — To tumble, skid, slip, take a walloping, a drubbing, to be manswadled, trimmed, whaled, scuttled, riddled, badly bent, bumped, slaughtered, nosed out, sent to the cleaners, counted out or laid on the cooling board. — “Some Baseball Slang,” Chicago Eagle, 20 Dec. 1913.
To the Cleaners (Money)
The first use of to the cleaners in the sense of losing money occurs in a humorous poem about making ends meet:
Economy the watchword is,
And we are careful gleaners.
In spite of that our pocketbook
Goes weekly to the cleaners.
Some new and patent food we need,
A substance cheap and lasting,
Or else I very greatly fear
We'll have to live by fasting. — Rock Island Argus (IL), 19 Feb. 1912.
Were this the only attestation, it could be dismissed as a nonce usage, a clever metaphor in a poem. The second usage, however, confirms that the expression has entered the language.
In 1912, a boxing promoter arranged a prize fight in Las Vegas — the one in the new state of New Mexico, which still had no law against such events. Local businesspeople had sponsored the fight with a $100,000 investment, $2.6 million today, and expected a return, both in media attention and tourist dollars:
EAST LAS VEGAS, N. M., JULY 2.— Las Vegas voraciously awaits the coming throng. Although the “citizens’ committee” has promised to keep the eats and flops within the reach of all, the dealers will not stand hitched and today’s bulletin shows that the price of eggs has flown and even the homely diet of “ham and” is reaching the aviating stage... This gang will never come again, the governor says so, at any rate—and why not send them to the cleaners while the time is ripe? — Abilene Daily Reporter (TX), 3 July 1912.
In this fight then, it was the fans who were sent to the cleaners, not the loser of the bout.
The expression, of course, was not limited to sports events:
A conviction is growing that there will be plenty of 8-cent hogs during the next ninety days, and that along toward March substantial figures will be written on sale tickets, provided, of course, that the country does not go to the cleaners in a financial and industrial sense meanwhile. — Chicago Livestock World, 13 Nov. 1913.
A lot of people go to the cleaners in this manner, which is called “speculation'” … And then take the other forms of gambling—cards, dice, roulette and what have you. It isn’t always the “Joints” that drag in the suckers. I’ve been taken to the cleaners more than once in a friendly game in somebody's parlor. — Rockland County Evening Journal (Nyack NY), 25 Apr. 1931.