This article traces the rise of John Lamont, a Highland planter in nineteenth-century Trinidad. The island was subsumed into the British Empire in 1802, the third wave of colonization in the British West Indies and just thirty-two years before slavery was abolished. Many Scots travelled in search of wealth and this article reveals how one West India fortune was accumulated and repatriated to Scotland. John Lamont travelled from Argyll in the early 1800s, eventually becoming part of the Trinidad's plantocracy class and recipient of a major sum of compensation on the emancipation of slavery in 1834. Unlike many other Scots in the British West Indies, however, Lamont remained in situ in the post-emancipation period and was thus an exception to the sojourning mindset identified in previous studies. Lamont's status as an ‘every-day planter’ undoubtedly contributed to his major fortune which, despite his residency in the colonies, was dispersed in the lower Highlands of Scotland amongst his paternal family, the Lamonts of Knockdow. The article also surveys modern representations of John Lamont: a Highland planter who, in his own words, achieved his wish to die ‘in harness’ in Trinidad.