Earliest John - Maryland 1640s
John demanded and was granted 100 acres of land along any neck of St. George's Creek in St Mary's County, Maryland on 19 Mar 1641 for transporting himself in 1640. The surveyor was told to lay out his land "before midsummer next on any Neck of St George's Creek. Assuming he was at least 20, as he declared he transported himself, this places his birth year before 1620. No survey was found, however, the 1641 entries in the land record are missing.
John was one of several men assessed 28 pounds of tobacco by the Burgess of the Assembly in St. Georges Hundred on 2 Aug 1642.
John was fined 20 pounds of tobacco because he did not appear before the General Assembly on 5 September 1642 in St Mary's. There seems to be some confusion, because later in the Assembly minutes John was excused from appearing because he was certified as a servant. No later record of John was found.
Morgan Prather (?), Rowland Chambers and John Marknell of Cecil County, Maryland posted bond for administering the estate of John Rutlick on 20 March 1717. The inventory of John Rutlig reported to the court in April of 1718 by Andrew Wallae and Ewen Ris shows a poor man with only one set of clothes, a small mare with tack, an old musket, one pen, and a set of compasses. John had no household goods, so was probably living with someone. No will was found, which is not unusual for an aged person with little to pass on, and the final accounts list payments for the doctor and funeral expenses, only.
Was this our John who was granted land in St Mary's County? There is no evidence that it is. If it were, he would have been over 90 and may have been approaching 100 - an exceptionally long life in colonial times.
Cecil County was created in 1674 from Baltimore and Kent counties. In 1622, Edward Palmer received a land grant for Palmer's Island, and in 1633 a Trading Post was established on the island, then a part of Virginia.  Land Patents and certificates date from 1649 in the area. The earliest deed was recorded in 1674. No Rutledge surname was found in a search of the early Cecil county land records.
Cecil County rent rolls from 1658-1724 do not have an entry for the surname Rutledge, or any deviation of the name. 
 Land Records, St Mary's County AB&H, page 104; MSA SE 23-6. These records jump from 1641 to 1650, but the page numbering does not reflect missing pages. 1641/42 entries are on pages around 60.
 Maryland State Archives, Proceedings and Acts of the General Assembly July - August 1642, Volume 1, page 144. https://msa.maryland.gov/megafile/msa/speccol/sc2900/sc2908/000001/000001/pdf/am1--144.pdf .
 Maryland State Archives, Proceedings and Acts of the General Assembly January 1637/8 - September 1664, Volume 1, page 167. http://aomol.msa.maryland.gov/000001/000001/html/am1--167.html .
 Maryland State Archives, Proceedings and Acts of the General Assembly January 1637/8 - September 1664, Volume 1, page 177. http://aomol.msa.maryland.gov/000001/000001/pdf/am1--177.pdf .
 Maryland Register of Wills, Cecil County, Bonds 1676-1750, page 277, image 114 of 240. Familysearch.org.
 Prerogative court (Administration Accounts), MSA S531, TB2, book 1, p194, https://msa.maryland.gov/megafile/msa/stagser/s500/s531/000000/000001/pdf/mdsa_s531_1.pdf
 Knauss, Christopher, Maritime Cecil County, Arcadia Publishing, Charleston, SC, LOC Card number 2007920919, page 15.
 Maryland State Archives, Cecil County Court, Land Records, Index, 1674-1810, MSA CE 134-1.
 Cecil County, Maryland Rent Rolls Index, https://www.familysearch.org/ark:/61903/3:1:3Q9M-CSTB-NQSQ?i=8&cat=514223