"There was the fiasco over Kevin Pietersen, the fiasco over Allen Stanford and his millions, they've tried three or four guys as captain," said Boycott.
"Now they've got Andrew Strauss who is quite a nice lad - he will do a decent job - but I'm not convinced he is a natural captain.
"It's a gift, to look after 10 other people and also to still look after your own game and play well, and at the same time be thinking two steps ahead of the game.
"When you're captain you can't just wait for things to happen. The great captains are thinking ahead."
Reflecting on the vexed number three slot, Boycott added: "If you look at the number three position, we have tried Ian Bell and Owais Shah, they're still talking about bringing Michael Vaughan back, and now are are trying Ravi Bopara. That is just one position.
"I don't feel we're getting the best out what we've got. Never mind shooting themselves in the foot, England have shot themselves in the head this winter."
England's two-Test series against the West Indies starts at Lord's tomorrow, with the first Ashes Test at Cardiff on July 8.
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