I sold cigar to desperate doctor who shouldn't encourage smoking (12)
I believe the answer is:
cardiologist
'doctor who shouldn't encourage smoking' is the definition.
'cardiologist' can be an answer for 'doctor' (cardiologist is a kind of doctor). I am unsure of the rest of the definition.
'i sold cigar to desperate' is the wordplay.
'desperate' indicates anagramming the letters (a desperate or pathetic spelling).
'i'+'sold'+'cigar'+'to'='isoldcigarto'
'isoldcigarto' anagrammed gives 'CARDIOLOGIST'.
Can you help me to learn more?
(Another definition for cardiologist that I've seen is " Specialist in heart disease".)