The fool with the lollipop? (6)
I believe the answer is:
sucker
This clue is a double definition.
'the fool' is the first definition.
('sucker' can be a synonym of 'fool')
'the lollipop?' is the second definition.
('sucker' can be a synonym of 'lollipop')
'with' acts as a link.
(Other definitions for sucker that I've seen before include "One easily fooled; base-of-stem shoot" , "baby?" , "Fool" , "Slangy victim or plant shoot" , "Underground shoot from shrub, or slang victim" .)