Much of what is known of Thomas Boleyn's life must be viewed through the lens of his famous daughter, Anne Boleyn. According to his contemporaries, Thomas was an unremarkable man. The one gift he seemed to possess was the ability to gather as many positions, honorifics, titles, and other accomplishments acquired through others more powerful than him.

Royals and established nobility of his generation likely regarded the Boleyn family as upstarts. They were only two generations removed from the merchant class. While Thomas' father and grandfather were very successful London merchants, with an earlier ancestor serving as Lord Mayor of London, it was only his father who held the noble title of knight.

His money and connections allowed him to receive various appointments that helped him to rise in society. When he was in his twenties, he was appointed keeper of the exchange at Calais and of the foreign exchange in England. He was also well-known to King Henry VIII, who considered him a good and regular companion. Henry bestowed land grants and other marks of royal favor upon Thomas, who seemed to define himself only through the honors given to him. Henry also sent him, as he did other colleagues and companions, abroad on diplomatic missions. Perhaps his greatest accomplishment in that regard had to do with his organization of the famous meeting known as The Field of the Cloth of Gold.

Time spent in France insured that Thomas and his children were well-versed in the French language and culture, necessary for those who wished to continue their social climb. As his daughter Anne's star began to rise, Thomas rejoiced in the increasing honors and favors that came his way. He was created Earl of Wiltshire and Ormonde, and began to attend Parliament. Next was the appointment as Lord Privy Seal. At this point Henry sent Thomas and others abroad to seek Papal approval for Henry's divorce from his first wife, Katherine of Aragon. Thomas and the others were unconvincing, with Thomas particularly memorable for his bumbling attempts to impress the Pope by kissing his toe and presenting him with a spaniel. Once he returned to England he took up residence at court.

Letters and records left by his contemporaries do not speak highly of him. After his daughter's execution he retired to his family home, where he died in 1539.