If I was the england captain I would force a transfer request whether chairman levy likes or not. Been at Tottenham Hotspur for years has limited his achievement and fight for trophies.
Been 27 year old and ageing he should be able to boast of trophies in his cabinet after been prolific all this year's for spurs with nothing to show for it. Also I don't see the team doing much next season.
Would be smart of him to consider a new challenge with several top clubs chasing for his signature. I believe Manchester city would be the best place for him no much competition in the attack after the departure of Kun Aguero to Barcelona.
He should find it suitable over there with many of national team players over there to give him soft landing and enable him adapt easily. Hope Harry and his manager pull the move before the transfer window closes.