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There are 5 clues with the answer 'SHOELESSJOE'
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CLUE
1.
Nickname of "Black Sox" outfielder Jackson who's a character in 18-Across and 32-Across: 2 wds.
2.
Black Sox fielder Jackson
3.
Legendary Black Sox slugger Jackson
4.
Jackson moniker
5.
His bat was called Black Betsy