Cromwell was educated as a civil lawyer but did not enrol at Doctors’ Commons, nor is there any evidence that he practised. Instead, he settled at Upwood, where his father granted him a 500-year lease of a house, the tithes and a few acres of meadow in 1583; the unusual duration of the lease may have been designed to evade liability for wardship. In 1597 he and his brother Richard† inherited the manor of Freckenham, Suffolk from their uncle Richard Warren†, which was quickly sold, while Cromwell received a further £100 at his father’s death in 1604.
Cromwell had no personal influence at Huntingdon, where he was returned in 1604, on the interest of his eldest brother Sir Oliver*, whose main seat at Hinchingbrooke lay less than a mile from the town. Although not recorded as having spoken in Parliament, he was named to two or three bill committees. He had no discernible interest in the bill to restrict trading rights in Southampton to freemen (added 29 May 1607), but John Arundell*, to whose estate bill committee he was named on 27 Apr. 1610, was his second cousin.
Cromwell does not seem to have stood for election again, but in 1614 either he or his brother Sir Oliver secured a seat for Christopher Hodson* at Mitchell on the Arundell interest. In January 1626 Cromwell tried to find a seat at Camelford or Bossiney for his nephew Richard Hampden*, by lobbying Arundell’s brother-in-law William Carnsew†, with whom he had trained as a civilian at Oxford; he was unsuccessful.
Cromwell subscribed £25 to the Virginia Company in the autumn of 1610, but was prosecuted for non-payment two years later.
Cromwell’s plans for his own estate changed abruptly after the death of his last surviving son in June 1626.
Cromwell’s health declined during his final years. In 1626 he was ‘affected ... with a grievous palsy’, and in January 1630 he was convalescing after ‘a long and most dangerous sickness’. He suffered ‘an ague’ a few months later, but recovered sufficiently to receive a visit from his nephew, Sir Thomas Barrington*.
