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2 results for BOOTLEGGER from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Sun Apr 17, 2022	32A	Rumrunner, e.g.	Emet Ozar	Shortz
Sat Dec 29, 2007	26D	One running for work?	Bob Klahn	Shortz

7 results for BOOTLEGGER from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Sat Jun 1, 1991	17A	Liquor smuggler	Bryant White	Maleska
Tue Jun 19, 1990	17A	Illicit-spirits dealer	Martha J. DeWitt	Maleska
Thu Jan 22, 1987	58A	Speak-easy supplier	Jim Page	Maleska
Mon Sep 10, 1979	32D	Roaring Twenties' character	Samuel K. Fliegner	Maleska
Sun May 15, 1966	17D	Salesman of sorts.	William Lutwiniak	Farrar
Fri Aug 19, 1960	60A	Relative of a black marketeer.	Unknown	Farrar
Fri May 3, 1957	20A	Specialist of the 1920's.	Unknown	Farrar

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19 ms