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In 1759 the young Wentworth made his first significant investment, joining a partnership in the purchase and development of land in the Lake Winnipesaukee area.
Wentworth sat on a committee of partners that oversaw the settlement of the community, which the investors named Wolfeboro.
In 1763 his father sent him to London to act on behalf of his merchant interests.
Based on his father's introductions, he was soon mingling with the upper levels of British society.
Among the connections he made was one with the Marquess of Rockingham, a distant relative ( although neither was apparently aware of this ) and a leading Whig politician.
In 1765 Wentworth, still in London, was appointed by the province as one of its agents.
That same year Rockingham became Prime Minister and led the repeal of the hated Stamp Act.
Whether Wentworth influenced Rockingham's decision is uncertain, but New Hampshire's other agent, Barlow Trecothick, drafted with Rockingham a position paper on the matter, and Wentworth was clearly sympathetic to colonial opposition to the Stamp Act.

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