Content to bring hearty chaps to extremes of penury (5)
I believe the answer is:
happy
'content' is the definition.
(content can mean happy or pleased)
'hearty chaps to extremes of penury' is the wordplay.
'hearty chaps' becomes 'hap' (I can't justify this - if you can you should believe this answer much more).
'to extremes of' says to hollow out the word (remove centre letters) (only the letters at the extremes of the word).
'penury' with its centre removed is 'py'.
'hap'+'py'='HAPPY'
'to bring' acts as a link.
Can you help me to learn more?
(Other definitions for happy that I've seen before include "Pleased; fortunate" , "Cheerful - dwarf" , "Well-pleased" , "Doc's smiling pal" , "Pleased, content" .)