Mason investigated the incident, pronounced the Shinnecock guilty and charged the whole community a fine of seven hundred pounds to be paid over a period of seven years. The fine was, of course, an impossible burden for the Shinnecock. It was an effective way to reduce their autonomy and place them at a disadvantage in any future relationship with the English. The payment of the fine was to be supervised by Wyandanch; this move reinforced the role of the Montauk sachem in Shinnecock affairs. The following fall Wyandanch assumed the role of spokesman for the Shinnecock before the Commissioner of the United Colonies in an appeal to reduce the fine to four hundred pounds. This request was quickly granted in a very clever move which now made it even more difficult for the Shinnecock to challenge Wyandanch's authority over their land. It also placed Wyandanch more firmly in the grip of the English because he would be held responsible if the Shinnecock did not pay.

The Southampton settlers chose this time of trouble to "clarify" the question of their eastern boundary. An unnamed Shinnecock "whom the sachem had appointed chief among our Indians" came with his wife to testify before a town meeting that the land sold to the English in 1640 went all the way east to Wainscot ". ..at least, or thereabouts." No Indians signatures appear on this document and no attempt was made to redraft or amend the 1640 deed. The sachem who sent the couple to testify may have been Wyandanch. The reluctance to mention any Indian names in the town record certainly raises questions about the legal significance of the testimony. It also demonstrates that the eastern boundary of the land sold in 1640 was probably not clear enough to hold up in the colonial courts. The Indian title to the land between Mecox and Wainscott does not appear to have been properly extinguished.

The efforts on the part of the English to give some credibility to Wyandanch's title of "Grand Sachem of Long Island's soon began to pay off. In the two years following Mason s visit, Wyandanch signed no less than seven deeds granting Indian land to the whites. In the same year as the house burning Wyandanch sold Secatogue land to the settlers in Huntington. He even sold land as far west as Hempstead in spite of objections raised by local sachems. In May of the following year he sold some Shinnecock land for the first time. Gardiner purchased a stretch of beach property running west from Canoe Place. The deed indicated that the Shinnecock were not even consulted about the sale of their own land. Gardiner later turned this land over to a settler named John Cooper. On May 12, 1659 Wyandanch sold another parcel of Shinnecock land located " . . . westward to the place called Pehecannache (Peconic), southerly to Potuncke (near West Hampton) to John Ogden." Two of the strategies defined by Jennings were at work in the negotiation which led to the signing of this document. The colonists made use of their puppet, but they also made sure that Wyandanch had no real choice in the matter by pressing him for payment of the fine. The Montauk sachem had no currency of his own to significantly reduce the debt. Ogden agreed to assist Wyandanch by paying a part of the debt in exchange for land.The precise amount is not mentioned, but it appears that neither Wyandanch nor the Shinnecock ever got a cent. In fact, Ogden expected the Shinnecock to pay him back! Eight years later Ogden was still extorting money from them. Writing from his new home in New Jersey he demanded, "... fourty pounds from Shinnecock Indians as in remaine of what became due to mee from them upon the tax of fire money..." If he were successful in this endeavor, the Shinnecock would have paid the fine twice, once in land and a second time in cash! The records, however, do not reveal the outcome of Ogden's avaricious design.

These two deeds also demonstrate the foresightedness of the English. They knew Wyandanch wouldn't live forever, so they prepared the way for his teenage son, Wiancombone, to succeed him as "Grand Sachem" over Long Island. Wiancombone's name appears in both of the above mentioned deeds as a party to the transaction. This procedure for the transfer of authority is as alien to band-level social systems as is the title of "Grand Sachem." The colonists were once again ignoring legitimate native political authority in order to facilitate the alienation of Indian land.