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Chaucer's Official Life by James Root Hulbert
page 96 of 105 (91%)
"dismissal." In addition he was in 1394 granted another annuity of
twenty pounds. In view of these facts it would seem that the only
definite evidence of Chaucer's poverty was the action for debt of L 14.
1s. 11d. in 1398, but the circumstances connected with it--the King's
letters of protection and the sheriffs inability to find Chaucer--are so
remarkable that we cannot draw certain inferences from it. [Footnote: See
Kirk L. R., p. XLVII f.]

Looking at all the facts, then, we must admit that they do not form any
proper basis for most of the assertions that have been made. They do not
constitute even the suggestion of proof that, when Chaucer lost his
controllerships and gave up his annuity, he was out of favour with the
King, that he was soon in dire financial straits, and that when again in
1391 he lost the clerkship of the works, he was out of favour and
pressed for money.

If we wish to guess at the reasons why Chaucer gave up his offices and
his pension, we can find plenty of sufficient motives. He may have left
the offices for several reasons; he had held the controllership of the
customs of wool for twelve years, a long time for the holding of such an
office in those days; he may therefore have left because he was tired of
them. He may have left them because some one had given him something
better-we know, for example, that in the year after he left the
clerkship of the works he was employed in some way by the King; so in
the earlier case he may have received some other office or employment
the record of which has not come down to us. From November 1386 until
November 1387 we know that Richard II was scouring the Midlands trying
to gather a force with which to oppose Gloucester; he may have employed
Chaucer as a secret messenger throughout that year. As to the annuity,
Chaucer may have surrendered it because he could get a good price for it
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