His paternal grandfather, Sir William Wentworth of Ashby Puerorum, was a younger brother of Thomas Wentworth, 1st Earl of Strafford His education seems to have been deficient; critics said that he was almost illiterate, by which they simply meant not reading Latin and ancient Greek and certainly, his spelling was appalling.
This, combined with his reputation among his enemies as a very poor public speaker would lead many to question his qualifications to be a diplomat.
[2] Thomas Wentworth saw much service as a soldier in the Low Countries, and was occasionally employed on diplomatic errands.
He did not inherit the Strafford fortune or the Jacobean house, Wentworth Woodhouse which passed to the second earl's nephew, Thomas Watson, son of his sister Anne.
[5] Throughout his Berlin embassy, Frederick I, King in Prussia repeatedly utilised Raby's presence to legitimise his newly acquired royal status.
[4] In Berlin, Raby also secured the services of Johann von Bodt and Thomas Eosander to design Wentworth Castle, at Stainborough in Yorkshire, built, largely directed by letter from a distance, from about 1710 to 1720.
The Pretender appointed him one of his "Lords Regent" in England and commander of the Jacobite forces north of the Humber.
[7] On the collapse of the Plot, the Government, while fully aware of his deep involvement, decided to take no action against him, and he lived out his last years in peace.