Henry was the only son of William Rosewell (1561–1593) and Ann Walkeden who were married at St Martins, London on 20 June 1588.
[1] Henry's grandfather was William Rosewell (c. 1520–1566) who was Solicitor-General to Queen Elizabeth 1559-1566 and owned a number of estates in Somerset and Devon.
[1][5] There is no evidence that Henry Rosewell practiced as a lawyer, however he was named in many litigations over money and property from c. 1614 to 1650 both as Plaintiff and Defendant.
[1] Sir Henry had family connections with those involved in both the Dorchester and Massachusetts Bay companies but it is doubtful whether he took an active part in either venture.
[1] He was evidently a Puritan and was brought before the Court of High Commission in 1634 for holding a private chapel at Forde Abbey.
[9] It has been suggested that Henry Rosewell was the model for the main character of Hudibras, a mock heroic narrative poem from the 17th century written by Samuel Butler.
Sir Henry became the scapegoat for the failure of the executors to supply the portions and was subject to a series of suits in Chancery from 1641 to his death in 1656.
The property had been partly wasted by William Rosewell, his father, and Sir Henry was obliged to part with more; lost probably in aiding his Parliamentarian friends, in unsuccessful ventures in America, while most likely a vast amount of it was spent in the Chancery proceedings in which he became involved, through, in an evil day, his having accepted the burdensome trust laid upon him by Sir John Drake'.
[13] She appears to have suffered greatly over the cost of the suits 'whereas in late years I have been involved in several troublesome lawsuits in order to the recovering of my just right, whereby I have contracted several debts and I had undoubtedly sunk under them had I not been supported beyond my expectations by some friends and principally by William Rosewell of Southampton Street in the parish of St Giles in the Fields Esquire'.
[citation needed] James, Frances B (1888), 'Sir Henry Rosewell – A Devon Worthy', Transactions of the Devonshire Association, 20, 113–122.