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Cheshire Academy alumni
James Van Der Beek
Talib Kweli
Eric Bloom
Robert Ludlum
J. P. Morgan
Francisco Garcia
Tarik Black (American football)
George A. Jarvis
Johannah Leedham
Pete Perreault
Lambert Hitchcock
Alberto Diaz, Jr.
Roberto Goizueta
Gideon Welles
Fabián Basabe
Eli Pemberton
Josh Jobe
Joseph W. Hasel
Chol Marial
Jamal Faulkner
Malik Golden
Geoffrey Cheney Ferris
Ricardo Greer
Virgil Horace Barber
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