Gambled and passed over about a hundred (5)
I believe the answer is:
diced
'gambled' is the definition.
(dicing is a kind of gambling)
'passed over about a hundred' is the wordplay.
'passed' becomes 'deid' (I can't explain this - if you can you should give a lot more credence to this answer).
'over' says the letters should be written backwards.
'about' is an insertion indicator.
'a hundred' becomes 'C' (Roman numeral).
'deid' in reverse letter order is 'died'.
'died' placed around 'c' is 'DICED'.
'and' is the link.
Can you help me to learn more?
(Other definitions for diced that I've seen before include "Cubed" , "Played with small cubes" , "Chopped; gambled" , "Chopped into cubes" , "getting the chop!" .)