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Answer:
CRONY
Possible Questions:
Buddy
Chum
Pal
Sidekick
Intimate
Friend
Good buddy
Familiar
Cohort
Bosom buddy
Close friend
Ally
Old pal
Confidant
Longtime pal
Friend that goes way back
Old chum
Old buddy
Mate, and a hint to the starts of this puzzle's four longest answers
Long-time pal
Close companion
Back-room fellow