During the Anglo-Scottish war of the Rough Wooing, Wyndham commanded a ship at the landing at Edinburgh in 1544. In December 1547 he sailed two ships to Dundee to support the English garrison at Broughty Castle commanded by Andrew Dudley. He investigated the River Tay towards Perth looking to rob church roofs to make lead bullets. On Christmas Day 1547 he burnt Balmerino Abbey and on 29 December he burnt Elcho nunnery. On land, he constructed a battery at Haddington called 'Wyndham's bulwark.' With James Wilford on 3 June 1548, he captured Dalkeith Palace, and razed the town by fire. However, near the end of the war, the English commander, the Duke of Rutland, was required to investigate Wyndham's activities capturing foreign merchant vessels in the Firth. These disputed prizes included a coal-ship, seven Norwegian vessels laden with meal, pitch and timber, 4 French ships, a small warship he gave to his nephew, John Luttrell, another ship laden with soap and madder, and others. On 29 March 1550, the day peace was declared in England, Wyndham was sent to Scotland with two post horses and five Scottish hostages to exchange for Luttrell, who had been captured at Broughty. Around 1550, Hans Eworth painted Wyndham's, Wilford's, and John Luttrell's portraits. Wyndham wears a powder flask at his neck and a gun over his shoulder inscribed, "TW, aetatis XLII.MDL," indicating he was 42 in 1550. In 1590, the picture was called, "Of Mr Thomas Wyndham drowned in the Sea returninge from Ginny." "Ginny", meaning Guinea, was the name used for the western part of Africa now including Nigeria. The voyage to Guinea was backed by George Barnes of London. The planned voyage was noted by the Imperial ambassador Jean Scheyfve. In May 1553 Scheyfve thought Wyndham might employ a Portuguese pilot called Pinteado and sail in July. Thomas Wyndham's crew for this 1553 expedition included a future noteworthy explorer in his own right, Martin Frobisher. Wyndham and his crew were received in person by the Oba of Benin City, who in turn traded with them. Wyndham died in 1554 at sea off Benin, on the return leg of his voyage. He left John Luttrell £100 in his will.
Family
The son of Sir Thomas Wyndham of Felbrigg and Elizabeth Wentworth, he was educated at Louvain University and possibly in Italy. Wyndham's half-sister Margaret married Andrew Luttrell of Quantoxhead and Dunster Castle in 1514, the father of John Luttrell. Thomas's wife's name in Bridget Mannock born 1520. Their son was called Henry, and the names of two surviving daughters in 1553 are unknown.
