The second appearance of Whittington's name in the city books is in 8
Richard II., when he was one of the eight common councilmen for Coleman
Street ward. In 11 Richard II. he is named as becoming surety to the
chamberlain in the sum of ten pounds towards providing money for defence
of the city. In the following year he appears to have been no longer a
member for Coleman Street ward. On the 12th of March, 1393, he is named
as then chosen alderman of Broad Street ward; and on 21st September of
the same year he was chosen by the mayor, William Staundon, one of the
sheriffs for the ensuing year.[3]

When Adam Bamme died in the year 1397, during his mayoralty, Richard II.
arbitrarily put Whittington in his place, and at the lord mayor's day of
that year Whittington again filled the office, being then regularly
elected.[4] From his will we find that this king, who was a member of
the Mercers' Company, to which Whittington was apprenticed, was an
especial patron of his. In 1400 he was excused from attending the
Scottish wars, and in 1406 he was again elected mayor. He rebuilt his
parish church, and Mr. Riley has printed in his valuable _Memorials_ (p.
578) the grant by Whittington of land or the re-building of the church
of St. Michael, Paternoster, "in the street called La Riole," called
after the merchants of La Riole, a town near Bordeaux, who had
established themselves there.

Whittington was knighted by Henry V., and in 1419 he was elected mayor
for the fourth time. It was in this year that John Carpenter commenced
the compilation of his famous _Liber Albus_. We see how highly this
distinguished citizen was appreciated from the writings of such men as
Grafton and Stow. Richard Grafton writes in his _Chronicle_ (1569, p.
433)--