Rick and Henry always succeeded on course (8)
I believe the answer is:
haystack
'rick' is the definition.
('haystack' can be a synonym of 'rick')
'henry always succeeded on course' is the wordplay.
'henry' becomes 'h' ('H' can be a synonym of 'henry').
'always' becomes 'ay'.
'succeeded' becomes 's' (genealogical abbreviation).
'on' means one lot of letters go next to another.
'course' becomes 'tack' (I've seen this before**).
'h'+'ay'+'s'+'tack'='HAYSTACK'
'and' is the link.
(Other definitions for haystack that I've seen before include "Rick of dried grass" , "Pile of dried grass" , "Pile of cut grass" , "Large mound of dried grass" , "Large pile of fodder" .)