Green’s Dictionary of Slang

(US black) a cruel overseer or employer, also attrib.

[1902		St Louis Republic (MO) 1 June 47/6: ‘I see [...] the soul of Simon Legree has at last become the soul of the nation!’].
1903		Courant (Cottonwood Falls, KS) 12 Mar. 4/2: There you have him. ‘The New Simon Legree’ [...] a type of a class called ‘captains of industry’.
1912		Literary Digest 30 Mar. 657/1: At last, after the long junket through the South, on which all managers are Simon Legrees, is ended, comes a welcome day when the new uniforms are donned [DA].
1918		Natchez Democrat (MS) 3 Aug. 4/2: [headline] Southern Gentleman, or Simon Legree?
1935		L.A. Times 24 Mar. II 3/2: SIMON LEGREE: Any director, especially one who drives those within his jurisdiction.
1949		Delta Democrat-Times (Greenville, MS) 12 June 4/3: Even today a brutal driving person is characterized as a Simon Legree.
1950		St Louis Post-Dispatch (MO) 13 Jan. 34/2: A union witness [...] gave the most detailed description of the Simon Legree incident at the hearing.
1968		Arizona Republic (Phoenix, AZ) 19 May 13/1: [headline] Old-Time Law Still Protects Us From Simon Legrees.
1978		Maledicta II:1+2 (Summer/Winter) 169: Simon Legree Any ‘slave-driving’ boss, especially a white man supervising blacks.