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Chapter XI of My Boyhood Days (1940; ছেলেবেলা / Chhelebela in Bengali) contains the following passage:

The old indigo factory was still standing, with the river Padma in the distance. The zemindari office was on the ground floor, and our living quarters on the upper floor. (...) Today, the blustering shouts of the sahebs are completely silent. Where is now the indigo factory's steward, that 'messenger of death'? Where the troop of bailiffs, loins girded up and lathis on shoulder?

The zemindari or zamindari were big landowners who also collected taxes. The lahti is "a long, heavy bamboo stick used by Indian police as a baton". The Wikipedia page about indigo does not mention any special significance attached to this colour.

Even if the former indigo factory is now used by the zamindar or one of his officers, it is not obvious why the "steward" would necessarily be a "messenger of death", since that phrase implies that he always announces death.

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In Hindu mythology, the god of death is Yama. His attendants are called yamaduut, literally Yama's messengers (duut). The Bengali original of ছেলেবেলা / chhelebelaa uses the phrase যমের দূত / yamer duut, "the messenger of Yama", rather than the substantive যমদূত yamaduut, but the reference is the same. The word yamaduut is the same in singular and plural forms.

It's the job of a yamaduut to approach at the moment of death, tell the dead person that they are now dead, and escort the person's soul to the afterlife. Naturally yamaduut are much feared. Metaphorically, any person whose presence foretells calamity can be called a yamaduut.

The word translated "steward" is দেওয়ান / deoyaan, which is the Bengali spelling for dewan. A dewan was a revenue officer. So the question asked here boils down to: "why would the dewan of an indigo plantation be feared enough to be equated with a yamaduut?"

Indigo planting in India was notoriously exploitative. Farmers were persuaded to replace food crops with indigo. The indigo plants were sold to them on credit, the interest rates being such that farmers could never pay down the principal. The accrued debt was passed on to their heirs. Entire generations of farmers were in servitude to the planters as a result. Farmers also received a paltry sum for their indigo crops, amounting to only about 2.5% of the market value.

As the revenue officer of the plantation, the dewan managed the accounts with the farmers. He would be the one who paid the farmers for their indigo plants, but more importantly, he would also be the one to collect the interest due on the loans made, as well as the tax due on the cultivated land. Since the latter amounts typically exceeded the payment the farmers received, any dealings with the dewan were frightening.

The equivalence between a dewan and a yamaduut could often be quite literal: E. De-Latour, a witness before the British commission to look into the conditions of the indigo trade, testified that "not a chest of Indigo reached England without being stained with human blood". Conditions finally reached the point where the peasant farmers rebelled against the planters. The Indigo Revolt began in 1859, just a couple of years before Tagore was born. The revolt was successful, insofar as measures were laid out that marginally improved conditions for the farmers. But by the turn of the twentieth century, the manufacture of synthetic indigo became commercially viable. Indigo plantation in India, being no longer profitable, came to an end.

This passage from Tagore's memoir, written in 1940, recalls this history from about a half-century previous. The indigo factory still stands, but it isn't used to manufacture indigo any more. The white planters, their dewans, and the bailiffs who served as enforcers against the farmers have all disappeared. But Tagore remembers the toll the exploitative system took on the peasants, particularly the fear inspired by the dewans, so great that they were regarded as yamaduut or Death's henchmen.

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