How to say he smiled to think what a fool he had been. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh自分自分(jibun) (pn,adj-no) myself/yourself/oneself/himself/herself/i/meが(ga) (prt) indicates sentence subject/indicates possessive/but/however/still/andなんとなんと(nanto) (adv) what/how/whatever愚か愚か(oroka) (adj-na,n) foolish/stupidで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.あったかとno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb考え考え(kangae) (n) thinking/thought/ideas/intentionて(te) (aux) indicates continuing action微笑んno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbだ(da) (aux) be/is/indicates past or completed action/indicates light imperative。(。) Japanese period "."    
kareha jibun gananto oroka deattakato kangae te hohoen da 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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Translation by marcelostockle
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