A plaque remaining from the Big Apple Night Club at West 135th Street and Seventh Avenue in Harlem.

Above, a 1934 plaque from the Big Apple Night Club at West 135th Street and Seventh Avenue in Harlem. Discarded as trash in 2006.

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Entry from August 22, 2016
“As crooked as Pearl Street”

"As crooked as Pearl Street” was a pet phrase of William S. Devery (1854-1919), a New York City police chief who directed the language to others. “He is more crooked than Pearl Street,” Devery said in August 1902 of James K. McGuire, ex-mayor of Syracuse and ex-chairman of the Democratic State Committee. “Sheehan was crooked as Pearl street, which hits Broadway twice,” Devery said in September 1902.

The New York City simile was seldom used by 1930 and is of historical interest today.


Wikipedia: William S. Devery
William Stephen Devery (January 9, 1854 – June 20, 1919) was the last superintendent of the New York City Police Department police commission and the first police chief in 1898. Devery and Frank J. Farrell later co-owned the New York Yankees baseball team.

26 August 1902, New York (NY) Times, “Devery in Defiant Mood,” pg. 2, col. 5:
“Say, Pearl Street touches Broadway at two points. Let McGuire (James K. McGuire, ex-mayor of Syracuse and ex-chairman of the Democratic State Committee—ed.) explain that. He is more crooked than Pearl Street.”
(Spoken by William S. Devery.—ed.)

18 September 1902, The Sun (Baltimore, MD), “Devery for Congress,” pg. 2, col. 1L
“(John C.—ed.) Sheehan was crooked as Pearl street, which hits Broadway twice, but he couldn’t hit the people of his district once.”
(Spoken by William S. Devery.—ed.)

Old Fulton NY Post Cards
17 September 1902, The Sun (New York, NY), “Carroll and Devery Win,” pg. 2, col. 1:
“Fellow Democrats,” he (William Devery—ed.) said, “I thank you one and all for this victory. It is not my victory. It is the people’s victory. We went in the fight against a man who is as crooked as Pearl street, and we beat him because we were on the level. Crooked ways don’t win out in this district.”

Old Fulton NY Post Cards
3 October 1902, New York (NY) Herald, pg. 5, col 5:
DEVERY’S VOLLEY OF NEW SIMILES
“That Man Hill’s as Crooked as Pearl Street,” He Says.

Chronicling America
22 May 1903, New-York (NY) Tribune, pg. 1, col. 6:
DOCKS, HIS ISSUE.
DEVERY OUT FOR MAYOR.
Murphy Pier Leases Crooked as Pearl-st., “Bill” Says

(...)
“If those docks were given out honestly, then what’s the matter with Pearl-st.? That street hits Broadway twice and looks pretty crooked, but it ain’t so crooked as those dock leases.”
(Spoken by William S. Devery.—ed.)

Chronicling America
17 April 1904, New-York (NY) Tribune, Illustrated Supplement, “Waldorf Room at the Newsboys’ Lodging House,” pg. 6, col. 3:
“W’y, dey can spiel off words as crooked as Pearl-st. an’ as long as Broadway, an’ w’en yer get ter t’e end of ‘em yer blowed to know w’ere yer started in at.”
(Spoken by a New York newsboy or “newsie.”—ed.)

Chronicling America
19 April 1904, Lewiston (ID) Evening Teller, “‘Big Bill’ Has Quit,” pg. 2, col. 2:
“They used to say I was as crooked as Pearl street, which hits Broadway twice,” is a favorite saying of his lately, “but no one ever proved nothin on me.”

Chronicling America
28 July 1905, The Sun (New York, NY), pg. 5, col. 5:
Everybody knows how crooked Pearl street is, or at least that it is crooked, but few know how it came to form almost a semicircle, beginning and ending on the line of Broadway. A student of local history explains it thus:

Soon after the Dutch settled on Manhattan they built a stockade, and that stockade followed the line of what is now Pearl street. As the settlers prospered they wanted more substantial houses and built them just inside the stockade. When the need for the stockade ceased to exist it was removed, and a row of houses grew up facing those that had been inside the stockade, thus creating a crooked lane, that has since become Pearl street.

Chronicling America
16 November 1909, New-York (NY) Daily Tribune, “The Talk of the Day,” pg. 6, col. 4:
The expression “as crooked as Pearl street” is a familiar one, but the term “straight as Republican Alley” is hardly known outside of real estate circles. It is frequently used by real estate brokers in describing their honesty of purpose. Republican Alley is no mythical thoroughfare. It extends from about the middle of the north side of Reade street, between Lafayette street and Broadway. It forms an “,” and its two dimensions make a perfect right angle.

Google Books
Psmith, Journalist
By P. G. Wodehouse
London: A. & C. Black
1915
Pg. ?:
“Everything in the East is as crooked as Pearl Street.”

Google Books
New York in Seven Days
By Helena Smith Dayton and Louise Bascom Barratt
New York, NY: R. M. McBride
1925
Pg. 43:
Absolutely opposite the Aquarium, across the street to the east, is Pearl Street, which is responsible for the old insult “crooked as Pearl Street.”

5 January 1930, Rochester (NY) Democrat and Chronicle, “Seen by a New Yorker at Large” by Demin Seymour, pg. 2C, col. 7:
“BIG BILL” HAS QUIT
Famous Detective Who “Also Ran” for Mayor of New York Lef Politics
(...)
Once in a while some native New Yorker employs the expression “as crooked as Pearl Street.” It is a colloquialism now almost defunct. Pearl Street, windingest in town, begins on Broadway, wanders towards the East River and comes back to terminate at Broadway.

7 March 1935, New York (NY) Herald Tribune, pg. 20, col. 1:
Marcus Pleads With ‘Boobs’ to Quit Numbers
Anti-Crime Counsel Lists 9 Ways to Crush Policy Racket in Radio Address
‘Why Not Poker at Home?’
Harlem Game ‘Crooked as Pearl Street,’ He Asserts

Posted by Barry Popik
New York CityStreets • Monday, August 22, 2016 • Permalink