Hopeless repositioning tree with spade (9)
I believe the answer is:
desperate
'hopeless' is the definition.
(similar in meaning)
'repositioning tree with spade' is the wordplay.
'repositioning' is an anagram indicator.
'with' says to put letters next to each other.
'tree'+'spade'='treespade'
'treespade' with letters rearranged gives 'DESPERATE'.
(Other definitions for desperate that I've seen before include "Miserable" , "Nearly hopeless" , "in a stew" , "Adept seer (anag)" , "Hopeless; extremely bad" .)