How to say he did his best; otherwise he would not have won the first prize. 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最善最善(saizen) (n) the very bestを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,尽くし尽くし(dukushi) (suf) all sorts of/all kinds ofた(ta) (aux-v) indicate past completed or action/indicates light imperative。(。) Japanese period "."さもなければさもなければ(samonakereba) (exp) otherwise/if not/or else一等賞一等賞(ittoushou) (n) first place prize/blue ribbonは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh取れno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbな(na) (prt) connects adj to noun/indicates emotion or emphasis/command/prohibitionか(ka) (prt) indicates question/indicates choice, doubt, etc.っただろうno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb。(。) Japanese period "."    
kareha saizen wo dukushi ta 。 samonakereba ittoushou ha tore nakattadarou 。
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2)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最善最善(saizen) (n) the very bestを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,尽くし尽くし(dukushi) (suf) all sorts of/all kinds ofたさもなければno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb一等賞一等賞(ittoushou) (n) first place prize/blue ribbonは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh取れno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbな(na) (prt) connects adj to noun/indicates emotion or emphasis/command/prohibitionか(ka) (prt) indicates question/indicates choice, doubt, etc.っただろうno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb    
kareha saizen wo dukushi tasamonakereba ittoushou ha tore nakattadarou
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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