With fluctuations of fortune, order to move money on roulette bet? (9)
I believe the answer is:
chequered
'with fluctuations of fortune' is the definition.
(as in a 'chequered life')
'order to move money on roulette bet?' is the wordplay.
'order to move money' becomes 'cheque' (as in a cheque for a bank).
'on' is a charade indicator (letters next to each other).
'roulette bet?' becomes 'red' (you might bet red or black on a roulette wheel).
'cheque'+'red'='CHEQUERED'
(Other definitions for chequered that I've seen before include "Squared up" , "having ups and downs in fortune" , "With career having varied fortunes" , "with unreliable fortune" , "lifetime of ups and downs" .)