unsuccessful
ausgespielt
bankrupt
blasted
blighted
broken
desolated
destitute
destroyed
devastated
done for
done in
fallen
finished
fortuneless
gone to pot
homeless
impoverished
in ruins
in the gutter
in the red
insolvent
irremediable
kaput
landless
moneyless
out of funds
overthrown
penniless
propertyless
ravaged
ruined
ruinous
spoiled
undone
wasted
without a sou
wrecked
have-not
poor person
airshow
back-alley
blackleg
blood-brain
calm-eyed
dodd
ellipsis-friendly
half-alligator
hopefull
light-fingered
lily-fingered
newly-joined
nimble-fingered
out-of-the-money
pandour
soft-featured
sure-thing
tinhorn
workless