Green’s Dictionary of Slang

1. an unpleasant person.

1896		Ade Artie (1963) 92: Do you think I’m goin’ out ridin’ with her and have a lot o’ cheap skates stoppin’ to play horse with her?
1903		‘Hugh McHugh’ I Need The Money 73: Get out of here, ye cheap skate.
1906		S. Ford Shorty McCabe 205: Some cheap skate of a private detective, eh!
1913		J. London Valley of the Moon (1914) 25: I tell you she’s some goods. Watch me go across an’ win her from them cheap skates.
1913		Van Loan ‘For Revenue Only’ in Lucky Seventh (2004) 210: When I got to going good, I made some of ’em take their signs off the fence. Cheap skates!
1929		(con. WWI) H. Odum Wings on My Feet 140: This girl [...] Would call ’em cheap skates, signifyin’ she had handsome, highbrown soldier hero.
1937		‘Boxcar Bertha’ Sister of the Road (1975) 211: Jones and Roxy and the rest of these cheap-skates who try to exploit misery and suffering ought to be thrown in the lake.
1960		J.P. Donleavy Fairy Tales of N.Y. IV i: She still thinks the guy who walked out on her is something. When he’s a phoney. A phoney cheapskate.

2. (also short skate) a mean, ungenerous person.

1896		Chicago Record 1 Feb. 13/1: A few ‘cheap skates’ who don’t even belong to the club, called a meeting at the Hotel [DA].
1897		Kansas City Jrnl (MO) 29 Nov. 6/5: A rich girl had m,arried a cheap-skate lawyer. The marriage had deteriorated as marriage with cheap skates does .
1905		H. Green Actors’ Boarding House (1906) 108: Cheap skates, astin’ me tuh Mink’s, mind yuh!
1912		Van Loan ‘Loosening Up of Hogan’ in Ten-Thousand-Dollar Arm 135: This short skate Hogan’s too stingy to have a right to any ideas about circulatin’ currency.
1914		R. Lardner You Know Me Al (1984) 75: In her letter she called me a cheap skate and she inclosed a one-cent stamp and two twos.
1922		S. Lewis Babbitt (1974) 164: The real cheapskate is the man who won’t lend to the Lord!
1934		(con. 1920s) J.T. Farrell Young Manhood in Studs Lonigan (1936) 368: Five. Five bucks. Who’ll fade. Come on, you cheapskates!
1940		D. Maurer Big Con 204: You are a cheap skate to send me a phony.
1953		J. Thompson Alcoholics (1993) 5: He had made Doc look like a cheapskate.
1966		C. Himes Run Man Run (1969) 149: The shoeshine boy gave him the silent treament reserved for cheapskates.
1976		Cab Calloway Of Minnie the Moocher and Me 166: He called me a cheapskate and a lousy friend.
1989		C. Hiaasen Skin Tight 298: Roberto Pepsical couldn’t believe the nerve of this cheapskate.
1999		N. Cohn Yes We Have No 86: Only a cheapskate looks at the bill.
2001		‘Randy Everhard’ Tattoo of a Naked Lady 127: Get a room, cheapskate!
2009		Gazette (Montreal) 9 June 4/2: He only leaves a dime for a tip. Cheapskate.