In 1750, a 29-year-old Thistlewood arrived in Jamaica with very few possessions but was immediately sought after as a plantation overseer, and by 1757 his wages had risen to £100 a year. A year later, that was increased to £120 a year. This was an enormous sum compared to the average wages of white British and North American labourers. Such wages allowed him to purchase slaves and hire them out. He could have continued to make more money working for others, but in the mid-1760s he decided to become an independent landowner, not as a rich sugar producer but as a modestly well-to-do market gardener and horticultural expert for Jamaica's western end. He acquired local respectability, often dining with his parish's wealthiest planters, and served in several local offices, including justice of the peace. After one lavish meal in 1778, Thistlewood and his fellow planters played cricket.