For about eight years after 1512 we hear nothing of Cromwell. A letter to him from Cicely, marchioness of Dorset, in which he is seen in confidential business relations with her ladyship, is probably earlier than 1520, and it is possible that Cromwell owed his introduction to Wolsey to the Dorset family. On the other hand, it is stated that his cousin, Robert Cromwell, vicar of Battersea under the cardinal, gave Thomas the stewardship of the archiepiscopal estate of York House. At any rate he was advising Wolsey on legal points in 1520, and from that date he occurs frequently not only as mentor to the cardinal, but to noblemen and others when in difficulties, especially of a financial character; he made large sums as a money-lender.
In 1523 Cromwell emerges into public life as a member of parliament. The official returns for this election are lost and it is not known for what constituency he sat, but we have a humorous letter from Cromwell describing its proceedings, and a remarkable speech which he wrote and perhaps delivered, opposing the reckless war with France and indicating a sounder policy which was pursued after Wolsey's fall. If, he said, war was to be waged, it would be better to secure Boulogne than advance on Paris; if the king went in person and were killed without leaving a male heir, he hinted there would be civil war; it would be wiser to attempt a union with Scotland, and in any case the proposed subsidy would be a fatal drain on the resources of the realm. Neither Henry nor Wolsey was so foolish as to resent this criticism, and Cromwell lost nothing by it. He was made a collector of the subsidy he had opposed--a doubtful favour perhaps--and in 1524 was admitted at Gray's Inn; but he now became the most confidential servant of the cardinal. In 1525 he was Wolsey's agent in the dissolution of the smaller monasteries which were designed to provide the endowments for Wolsey's foundations at Oxford and Ipswich, a task which gave Cromwell a taste and a facility for similar enterprises on a greater scale later on. For these foundations Cromwell drew up the necessary deeds, and he was receiver-general of cardinal's college, constantly supervising the workmen there and at Ipswich. His ruthless vigour and his accessibility to bribes earned him such unpopularity that there were rumours of his projected assassination or imprisonment. All this constituted a further bond of sympathy between him and his master, and Cromwell grew in Wolsey's favour until his fall. His wife had died in 1527 or 1528, and in July 1529 he made his will, in which one of the chief beneficiaries was his nephew, Richard Williams, alias Cromwell, the great-grandfather of the protector.