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Answer:
SADSACK
Possible Questions:
Oaf
Bumbler
Schlemiel
Pathetically inept person
Pathetic person
Inept person
Born loser
Perennial loser
Hapless sort
Bumbling loser
Woefully inept person
Pathetic bumbler
Inept G.I.
Hopelessly inept fellow
GI washout
Debbie downer
Comics soldier (with "The")
Cartoon private
Blunderer
Army cartoon character