Jackson grew up in Berwick alongside several namesakes, and it is difficult to elucidate his early life from the surviving records. The son of a local merchant, he was already a prominent member of the town’s corporation by 1599, when he was chosen as that year’s elected alderman.
Although returned to the 1621 Parliament as Berwick’s junior rather than senior Member, Jackson took the lead in defending the borough’s interests. On 12 Mar., responding to a bid to end Berwick’s traditional exemption from the payment of subsidies, he successfully moved for this privilege to be upheld, reminding the House that it was enshrined in the borough’s charter. He complained on 21 Apr. about the impact on the town’s trade of a patent for the supply of salmon and lobsters to London. According to several accounts, it was Jackson rather than Sir William Grey who introduced on 26 May a proviso to exempt Berwick and Newcastle from the bill against wool exports, a move which was rebuffed on the grounds that it was procedurally premature. Undeterred, Jackson tried again when the bill received its third reading on 30 Nov., only for the proviso to be rejected outright. His proposal later in the same debate that exports via Scotland should also be banned was similarly dismissed.
In 1622 Jackson was still actively engaged in the financial management of the Berwick bridge project. When he leased a number of properties in the town which had formerly belonged to the garrison, he was described in the borough records as ‘a profitable member of this corporation ... [who] hath done many good offices for the wealth thereof’. However, by now he had also acquired the Kent manor of Chatham, and may have been contemplating retirement, since he relinquished his customs role in the following year.
Jackson ceased to feature in the corporation’s proceedings after June 1624, and presumably settled at Chatham. In April 1625 the duke of Buckingham requested that he use his local influence in support of Sir Albertus Morton*, who was standing for election as a Kent knight of the shire. How Jackson responded is not known, but later that month he was again elected as a Berwick Member, one of his relatives vouching in his absence that he would pay his own expenses. He failed to feature in this Parliament’s records, though he presumably attended at least the Westminster sitting. On 6 July he was appointed by Berwick corporation to help collect £1,000 promised by Charles I towards the cost of rebuilding the parish church.
In January 1626 Jackson was once again notified by letter of his return in Berwick’s latest parliamentary election. He was named on 9 Mar. to the legislative committee concerned with unseasonable malt production, and was probably responsible for the proviso introduced five days later in another unsuccessful bid to exempt Berwick from the bill against wool exports. Around the end of this month he requested his borough corporation to draft a petition, presumably for submission to Parliament, but its intended contents are not known.
Jackson’s rise up the social ladder was confirmed in 1630, when his daughter married a son of Henry Carey*, 1st earl of Dover, whose own father (John Carey†) had once served as acting governor of Berwick.
