Il n'aurait jamais dû miser tout son capital.

Questions & Answers about Il n'aurait jamais dû miser tout son capital.

Why do we use aurait dû to mean "should have"?
Aurait is the conditional form of avoir (would have), and is the past participle of devoir (to have to / must). Literally, it translates to "would have had to", but in French, the conditional past of devoir is the standard way to express "should have" for regrets and reproaches.
Why is the negation n' ... jamais placed around aurait?
In compound tenses like the conditional past, negative words like ne ... jamais (never) wrap around the conjugated auxiliary verb. Here, the auxiliary is aurait, so it becomes n'aurait jamais. The past participle () and the infinitive (miser) come right after.
Why does have a circumflex accent (ˆ) over the u?
The accent distinguishes the past participle of devoir () from the partitive article du (meaning "some" or "of the"). Note that the accent is only used on the masculine singular form of the past participle; the feminine and plural forms drop it (due, dus, dues).
Why is miser in the infinitive here, instead of a past tense form?
When a conjugated verb (even a compound one like aurait dû) is followed directly by another verb, the second verb stays in the infinitive. Here, miser (to bet) is the action he "should not have" done, so it stays in its dictionary form.
Why is it tout son capital and not tous?
Tout acts as an adjective here and must agree with the noun it modifies. Since capital is a masculine singular noun, we use the masculine singular form tout. If it were plural, it would be tous ses capitaux.

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