As mentioned above, Henry Kendall was the ward of Hastings in 1567. If he married in 1570, then his children could include GK and his elder brother whose name we do not know. If either of these two participated in the 1585 Roanoke expedition, they might have been referred to as ‘Master Kendall’. George Kendall, the Queen’s Scholar at Westminster, and his brother clearly had sufficient connections to Court and to the Cecils, and this would have made their participation in such a voyage possible. If either of them was on the Roanoke expedition, then it would have been natural for them to be chosen to go in 1606.
Feudal obligations to a superior Lord gave way to patronage from those who were in a position to ease the progress of relations, friends, business associates or others that might prove to be useful. In Tudor times this was at work for the Dudleys, and the Cecils were also adept at gathering supporters for their causes. GK received support from Cecil because he could provide a useful service, but also I suspect because familial connections were persuasive in that regard. If GK had the connections indicated above to the West, De La Warr family, then they too may have sponsored his involvement in the Jamestown expedition and the earlier Roanoke expedition.
GK’s brother Edward was clearly closely involved with activities on behalf of the Russell sisters, who were aunts through marriage to Robert Cecil (Tree 1). In 1600 GK asked Robert Cecil to look after his brother Edward, and in 1606 he set sail for Virginia.
Anne Russell, Lady Warwick, died in February 1603, and Elizabeth Russell, Lady Bath, died in March 1605. The third sister of interest was Margaret, married to George Clifford, Earl of Cumberland. Their inheriting daughter was Anne Clifford.
It seems certain that Robert Cecil granted GK’s request. From the State Papers:
26.11.1603 – Grant, with survivorship, to Edw. Kendall and John Bendbo, of the office of Remembrancer of First Fruits in the Exchequer. (John Bendbo, Deputy Clerk of the Crown in Chancery, died 7.10.1625)