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There's a particular type of prolepsis in Greek which is often called "lilies prolepsis" because of the most famous example:

καταμάθετε τὰ κρίνα τοῦ ἀγροῦ πῶς αὐξάνουσιν
Consider the lilies of the field, how they grow
(Matthew 6.24)

This occurs as far back as Homer:

ᾔδεε γὰρ κατὰ θυμὸν ἀδελφεὸν ὡς ἐπονεῖτο
For he knew in his mind his brother, how he was troubled
(Iliad 2.409)

And even appears occasionally in English:

[I] watch'd him, how he singled Clifford forth
(Shakespeare, Henry VI II.1.12)

(Examples from Fraser, Consider the lilies: prolepsis and the development of complementation.)

Does this sort of prolepsis ever appear in native, Classical Latin (as opposed to the Greek-influenced Latin of the Vulgate)? Is it attested in prose or poetry, or both?

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    Interesting -- I'd never heard this called "lilies prolepsis". In case it's useful, in transformational syntactic terms this is an instance of subject-to-object raising. – TKR Jun 30 '17 at 2:36
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Cicero, Ad familiares 8.10.3:

nosti Marcellum, quam tardus et parum efficax sit, itemque Servium, quam cunctator.
'You know Marcus, how slow he is and how ineffective, and likewise Servius, what a dawdler he is.'

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