Will he trundle the hoop? (5)

I believe the answer is:

rollo

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'will he' is the definition.
'Rollo' can be an answer for 'he'. I'm not certain of the 'will' bit.

'trundle the hoop?' is the wordplay.
'trundle' becomes 'roll' (I've seen this in another clue).
'the hoop?' becomes 'o'.
'roll'+'o'='ROLLO'

Can you help me to learn more?

(Other definitions for rollo that I've seen before include "First duke of Normandy" , "Viking founder of Normandy dukedom" , "Boy" .)

I've seen this clue in the Evening Standard.

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