I did have two generations of Henrys before John?s father Thomas, but this is apparently an error brought in by the Visitation. (See notes for the Cotesfords)
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Seems from this that he was a younger son:
The manors of Osbourne and Wood in the Isle of Wight passed from John Malwayn to Sir Thomas Raleigh, Sheriff of Warwickshire and Leicestershire who died in 1398 [1396?] leaving a son, Thomas who died in 1404, and was succeeded by his son, William. William Raleigh died unmarried in 1419 and was succeeded by his sister, Joan, who married Edward Bromflete but the Manor passed on Joan's death to her cousin, William Raleigh, who died in 1460 possessed of Woodhouse in Whippingham, leaving a son, Sir Edward Raleigh who died in 1512.
(http://www.woottonbridgeiow.co.uk/Properties/Woodhouse.htm)

• Married: BEF 1396

1. William Raleigh

1. Type: Web Site
   Title: Neale S. Brown
   Author: Neale S. Brown
   URL: http://worldconnect.rootsweb.com/cgi-bin/igm.cgi?op=SHOW&db=rebcav&recno=0