In 1502 he participated in identifying potential supporters of Edmund de la Pole, 3rd Duke of Suffolk, who was believed to be planning a rebellion against Henry VII.

In 1517 during the reign of Henry VIII, Spring was given exemption from public duties, possibly as a result of being suspected of underpaying tax, at which point he was probably at the height of his wealth.

[10] By the time of his death, Spring was believed to be the richest man in England outside the peerage, having invested much of his money in land.

[14] Spring is mentioned in John Skelton's satirical poem Why come ye not to Court, which makes reference to the rich clothier, with whom Skelton is said to have been friends, and his refusal to attend court:[11] Like his father, Thomas Spring was closely involved in the reconstruction and embellishment of St Peter and St Paul's Church in Lavenham.

The rebuilding also gave Spring an opportunity to display his wealth and generosity, thus solidifying his position in Suffolk; a common motivation behind the construction of many similar wool churches.

Thomas, her second husband, had owned 25 East Anglian manors and Laverham had become the fourteenth richest English town.

His widow, Alice, commissioned Flemish wood carvers to create a ten-foot high parclose screen around his tomb, which is one of the most intricate still in existence.