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2 results for BOLDEST from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Thu Aug 21, 2008	67A	Most brazen	Gary J. Whitehead	Shortz
Tue May 14, 2002	45A	Most fearless	Barry Callahan	Shortz

5 results for BOLDEST from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Sun Aug 7, 1988	89D	Least timorous	Maura B. Jacobson	Maleska
Sun Oct 3, 1976	105A	Most conspicuous	Bert Rosenfield	Weng
Fri May 9, 1969	39A	Most nervy.	Unknown	Weng
Sat May 28, 1960	57A	Least afraid.	Unknown	Farrar
Sat Mar 21, 1959	43D	Most daring.	Unknown	Farrar

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