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The Identity of Roger PRESTON of Ipswich
Below is my attempt to describe and resolve a "bad connection" made with regard to the ancestry of Roger PRESTON of Ipswich.
UPDATE some say William Bowker Preston was right, that Roger PRESTON of Ipswich is the son of Roger PRESTON of Up-Ottery.  I will look further into the evidence.
New development much more on the 1649 lawsuit in:
Peter Wilson Colham.  1981.  "Genealogical Gleanings in England." National Genealogical Society Quarterly 69(2): 115-123 (Broderbund CD-210).
Will transcribe and post as soon as I can find time.
The man often described as "Roger PRESTON of Ipswich" is so-called because the first mention of him in America was in 1639 as owner of land in Ispswich, Essex Co., MA, where he lived until 1658 when he moved to Salem.1  We know, however, from passenger lists that he sailed for Boston in 1635 on the Elizabeth, at the age of 21.2, 3  Unless he was lying about his age, he therefore must have been born in 1613 or 1614 (depending on whether he had or had not had his birthday yet that year before his departure).

The LDS Ancestral File shows Roger PRESTON of Ipswich, MA, as the son of Roger PRESTON (who died in 1638) and Alice PARRY, of Up-Ottery, Devonshire, England.4   The ancestry of Roger PRESTON of Up-Ottery is given by William Bowker Preston in his book, The Preston Genealogy.He shows a Roger PRESTON, Jr., of Up-Ottery, son of Roger and Alice (PARRY) PRESTON, with a wife named Martha.   The wife of Roger PRESTON of Ispwich was named Martha; and, although William Bowker Preston does not come right out and say that his Roger PRESTON, Jr., is Roger PRESTON of Ipswich, he certainly leaves the door open to that interpretation and many have entered.  There is, however, no proof that they are the same individual.  In fact, there is proof that they are not.

According to Coldham6, there was a lawsuit recorded in 1649 in London involving Roger PRESTON:
 

Chancery case of Roger Preston v. Thomas Lyon and John Spencer, executors of the will of John Hollam, executor of the will of Mary Preston, re the estate of Roger Preston, father of the plaintiff. Deponents include Marie Laurence aged 39, wife of William Laurence, planter of Virginia, who declared that she and her husband came to England from Virginia with Roger Preston in 1638 after the death of Roger Preston the elder.

This Roger Preston certainly sounds like the Roger Preston, Jr., who was son of Roger Preston, Sr., "of Up-Otterly, Devon," who died in 1638.  And if he is, how can the fact that he came back to England from Virginia not Massachusetts be explained?

Still referencing Coldham6, there is a Roger Preston in the early "censuses" of Virginia (ages are shown after the name, followed by ship and date of arrival, when known apparently, "Jordan's Journey" is a placename):
 

20 January 1625. - 7 February. 
Musters of the inhabitants of Virginia...
Jordan's Journey (21 January)...
servants...
Roger Preston, 21, by Discovery March 1621...

If this Roger Preston was 21 years of age on 21 Jan 1625, then he was born in either 1604 or 1603, depending on whether he'd had his birthday yet that year.   Surely, it is this Roger Preston, the one born 1603/4 who went to Virginia in 1621 not the one born 1613/4 who went to Massachusetts in 1635 who is the one who returned to England in 1638 upon the death of his father and who filed a lawsuit in London in 1649. This man is Roger Preston, Jr., of Up-Otterly.

And now the interesting question is:   How did the son of a landed gentleman end up an indentured servant in Virginia? And what was the outcome of the lawsuit over his father's estate? Did he win, regain the family lands, and stay in England? Did he dispose of the estate and return to the New World with money in his pocket?  Or did he lose his case?

Sources:

1.  The Preston/Lindsey Trail.  1995.  Self-published by Rosaline Preston (17369 Road 6 SE, Warden, WA 98857) and Carol Huber  (10508-A Witter Springs Rd., Witter Springs, CA 95493).

2.  John C. Hotton.  1931. The Original Lists of Persons of Quality.  G.A. Baker & Co., Inc., NY.  On p. 35:

8 Aprilis 1635.  Theis pties herevnder mencioned are to be transported to New England: imbarqued in the Elizabeth of London Wm Stagg Mr. [master] bound thither: they have taken the oath of Allegeance & Supremacie p Cert: from the pish of St. Alphage Cropplegate the Minister there,
Tanners: Wm Holdred, 25; Roger Preston, 21; Daniell Brodley, 20.
That theis 3 pties are no Subsedie men: wee whose names herevnto are written belonging to Blackwell Hall, do averr they are none.  Robte Farrands.  Thomas Smith.

3.  Peter Wilson Coldham.  1988.  The Complete Book of Emigrants, Volume 1, 1607-1660.  Genealogical Publ. Co., Baltimore, MD (Broderbund CD-350), citing E157/20, Public Record Office (Chancery Lane, London WC2A 1 LR, England):

6-17 April 1635.  Passengers embarked in the Elizabeth, Mr. William Stagg, bound from London to New England...
William Holdred 25, Roger Preston 21, Daniell Brodley 20 and Isack Studman, tanners of St. Alphage Cripplegate...

4.  LDS.  Family Search: Internet Genealogy Service:  AF - Ancestral File (online at FamilySearch.org). 

5.  William Bowker Preston.  1900.  The Preston Genealogy: Tracing the History of the Family from about 1040, A.D., in Great Britain, in the New England States, and in Virginia, to the Present Time.  Self-published (online at GenealogyLibrary.com).  The Preston pedigree based on William Bowker Preston's book is posted on my web site under the title, Descendants of Leolphus de Preston of Scotland

6.  Peter Wilson Coldham.  1988.  The Complete Book of Emigrants, Volume 1, 1607-1660.  Genealogical Publ. Co., Baltimore, MD (Broderbund CD-350), citing C6/42/94 and C24/727/114, Public Record Office (Chancery Lane, London WC2A 1 LR, England).

Family Group Sheet of Roger PRESTON of Ipswich
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