Sift through leftovers with a thousand dollar rake (5)
I believe the answer is:
glean
'sift through leftovers' is the definition.
'glean' can be an answer for 'sift' (thesaurus). I am not sure about the 'through leftovers' bit.
'with a thousand dollar rake' is the wordplay.
'with' is an insertion indicator.
'thousand dollar rake' becomes 'glen' (I can't explain this - if you can you should give a lot more credence to this answer).
'a' placed within 'glen' is 'GLEAN'.
Can you help me to learn more?
(Other definitions for glean that I've seen before include "Gather, pick up" , "Gradually put together" , "Collect gradually (from various sources)" , "Learn by gathering bits" , "Pull together from various sources" .)