Ray’s holding the money again, we gather (5)
I believe the answer is:
rally
'gather' is the definition.
(rallying is a kind of gathering)
'ray's holding the money again' is the wordplay.
'holding' is an insertion indicator.
'the money again' becomes 'll' (I can't justify this - if you can you should believe this answer much more).
'ray' placed around 'll' is 'RALLY'.
'we' acts as a link.
I am not very happy about this link. It may belong to another bit of the clue.
Can you help me to learn more?
(Other definitions for rally that I've seen before include "Mass meeting; car race" , "Regain one's strength" , "Recover; mass meeting" , "Get-together" , "Arouse for action" .)