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Pleshcheyev came from an ancient noble family. In 1719 he was appointed deputy to the governor of Siberia, A.M. Cherkassky. Later he was appointed president of the Kamer-Collegium by a royal decision. On the accession of Catherine I, he was raised to the rank of major-general.
Lip to the appointment of I.F. Romodanovsky, Pleshcheyev was in charge of the Moscow gubernia. In February 1728, on the day of the coronation of Peter II, Pleshcheyev was given the rank of privy counsellor, and on 18 May he became a member of the Senate while continuing his duties of a governor. Following the resignation of Romodanovsky and up to the appointment of V.F. Saltykov, Pleshcheyev was once again in charge of the gubernia.
It is worth noting that all previous decrees on paving in Moscow related only to the streets of the city and not to the city squares, where mud made trade and tax collection difficult.
In order to facilitate tax collection, a decree was issued by the governor on 27 June 1729, On the Paving of Trading Sites in Moscow, under which the gubernia office was instructed "to pave with stone, taking advantage of the present convenient time, Polyanka by the Red Church, where people from surrounding towns gather for trade and the collection of local taxes..." However, this was not the only concern of the city authorities. Major-General Volkov, dispatched to Moscow in February 1727 to organise minting, wrote: "Permit me to take my leave of this abysmal place. I truly fear that I shall be taken ill: the thaw began only two days ago, but the local cleanliness, of which you have heard, has given rise to such an odoriferous air and such a heavy mist that it is impossible to leave my cabin."
Pleshcheyev's appointment as governor of Siberia under a decree issued on 28 September 1730, was connected with his activities in the Supreme Privy Council, which was seeking to restrict the autocratic powers of Anna loannovna. In 1735, when he was governor of Tobolsk, Pleshcheyev came under investigation on charges of unlawful activities.
In 1736 he was dismissed from his post on grounds of "weak health", and sent to Moscow. In 1738 he became chief judge at the Justice Office, and in 1740 he was made president of the Siberian Office. That same year he was relieved of "the penalty fine for the Siberian affair".
Pleshcheyev died in Moscow and was buried at the Monastery of the Epiphany.
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