How to say you should have known better than to lend him money. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.金(kin) (ok) money/metal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,貸し貸し(kashi) (n) loan/lending/favor/favour/debt of gratitude/creditor/method of lending/credit sideたらたら(tara) (conj,prt) indicates supposition/if ... then/when/after/ indicates exasperationダメダメ(dame) (adj-na,n) no good/not serving its purpose/useless/broken/hopeless/wasted/in vain/purposeless/cannot/must not/not allowedだってだって(datte) (conj) after all/because/but/even/too/as well/also/they say/i hear/you meanことこと(koto) (prt) particle indicating a command/particle indicating mild enthusiasm/particle indicating a gentle interrogative/particle used to soften a judgment or conclusion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,分(fun) (n) minuteか(ka) (prt) indicates question/indicates choice, doubt, etc.っていようもno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question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,。(。) Japanese period "."    
kare ni kin wo kashi tara dame dattekotowo waka tteiyoumonowo 。
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