Political career
In 1715, Stanhope entered the House of Commons as Lord Stanhope of Shelford and as member for St Germans. Later, when the impeachment of James Butler, 2nd Duke of Ormonde came before the House, he used the occasion (5 August 1715) to try out the result of his rhetorical studies. His maiden speech was fluent and dogmatic, but upon its conclusion, another member, after first complimenting the speech, reminded the young orator that he was still six weeks short of his age of majority and consequently liable to a fine of £500 for speaking in the House. Lord Stanhope left with a low bow, and set out for the Continent.
While in Paris, he sent the government valuable information about the developing Jacobite plot. In 1716, he returned to Britain, resumed his Commons seat and became known as a skilled yet tactful debater. When George I quarrelled with the Prince of Wales the same year, Lord Stanhope remained politically faithful to the Prince but was careful not to break with the King's party. However, his continued friendly correspondence with the Prince's mistress, Henrietta Howard, earned Chesterfield the personal hatred of the Prince's wife, Princess Caroline of Ansbach. In 1723, he was appointed Captain of the Gentlemen Pensioners. In January 1725, on the revival of the Order of the Bath, the red ribbon was offered to him, but Stanhope declined the honour.
Upon his father's death in 1726, Stanhope became the 4th Earl of Chesterfield and assumed his seat in the House of Lords. His inclination towards oration, often seen as ineffective in the House of Commons because of its polish and lack of force, was met with appreciation in the House of Lords, and won many to his side. In 1727 the Prince of Wales succeeded his father, becoming King George II. In 1728, in service to the new king, Chesterfield was sent to the Hague as ambassador to The Netherlands, where his gentle tact and linguistic dexterity served him well. As a reward for his diplomatic service, Chesterfield received the Order of the Garter in 1730, the position of Lord Steward, and the friendship of Robert Walpole, the de facto head of the government. While a British envoy in the Hague, he helped negotiate the second Treaty of Vienna (1731), which signalled the collapse of the Anglo-French Alliance, and the beginning of the Anglo-Austrian Alliance. In 1732, Madelina Elizabeth du Bouchet, a French governess, gave birth to his illegitimate son, Philip for whom Chesterfield wrote the Letters to his Son giving advice on life. In 1731, while at The Hague, Chesterfield initiated the Grand Duke of Tuscany (later to become Francis I, Holy Roman Emperor) from the House of Habsburg-Lorraine into Freemasonry, which was at the time being used as an intelligence network by the British Whigs. By the end of 1732, ill health and financial troubles caused Chesterfield's return to Britain and his resignation as ambassador.
In 1733, Chesterfield married Melusina von der Schulenberg, the Countess of Walsingham, who was the illegitimate daughter of Melusine von der Schulenburg, Duchess of Kendal by George I. After recuperating from his illness, Chesterfield resumed his seat in the House of Lords, where he was now one of the acknowledged leaders. He supported the ministry and leadership of Robert Walpole, but withheld the blind fealty that Walpole preferred of his followers. Lord Chesterfield strongly opposed the Excise Bill, the Whig Party leader's measure, in the House of Lords, and his brothers also argued against it in the House of Commons. Even though Walpole eventually succumbed to the political opposition to the bill and abandoned the measure, Chesterfield was summarily dismissed from his stewardship. For the next two years, he led the opposition in the Upper House to effect Walpole's downfall. During that time, he resided in Grosvenor Square and became involved in the creation of a new charity called the Foundling Hospital of which he was a founding governor.
In 1741, Chesterfield signed the protest calling for Walpole's dismissal and then went abroad on account of his health; after visiting Voltaire in Brussels, he went to Paris where he associated with writers and men of letters, including Crebillon the Younger, Fontenelle and Montesquieu. In 1742, Walpole's fall from political power was complete, but although he and his administration had been overthrown in no small part by Chesterfield's efforts, the new ministry did not count Chesterfield either in its ranks or among its supporters. He remained in opposition and distinguished himself by the courtly bitterness of his attacks on George II, who began to hate him violently.
In 1743, Chesterfield began writing under the name of "Jeffrey Broadbottom" for pamphlets and a new journal, Old England; or, the Constitutional Journal, which appeared (broad bottom being a term for a government with cross-party appeal). In parallel with the journal, Chesterfield and George Bubb Dodington also patronised paired opposition histories: William Guthrie’s A General History of England (planned to 1688) and James Ralph’s The History of England, During the Reigns of King William, Queen Anne, and King George I (1744–46).
A number of pamphlets, with which Chesterfield had the help of Edmund Waller, followed. His energetic campaign against the King and his government won the gratitude of the Dowager Duchess of Marlborough, who left him £20,000 as a mark of her appreciation. In 1744, the King was compelled to abandon Lord Carteret, the successor to Walpole, and the coalition for a "Broad Bottom" party, led by Chesterfield and Pitt, came into office in coalition with the Pelhams.
In the troubled state of European politics, the Earl's calm conduct and diplomatic experience were more useful abroad than at home, and he was sent to The Hague for a second time as ambassador. The object of his mission this time was to persuade the Dutch to join in the War of the Austrian Succession and to arrange the details of their assistance. Success was quickly achieved, and on his return a few weeks afterwards, he received the Lord-Lieutenancy of Ireland, which he had long coveted.
Chesterfield's short administration (January 1745 – November 1746) in Ireland was effective, as he repressed the corruption traditional to the office, and established schools and factories. He was the first official to allow Dubliners to roam in Phoenix Park, and installed the central "Phoenix Monument", a phoenix bird on a Corinthian column (the 2.8 mi main road through the park is still known as Chesterfield Avenue). He worked with, and pacified, both the Protestant Orange Order and Roman Catholic Jacobite factions; as a result, Irish Jacobites did not assist the Jacobite rising of 1745. Anecdotally, upon being roused for a false alarm of an Irish rebellion and being told that "the papists in Ireland are all up!", he replied: "I am not surprised at it, why, it is ten o'clock, I should have been up too, had I not overslept myself".
In 1746, however, he had to exchange the Lord-Lieutenancy for the post of Secretary of State. Chesterfield had hoped to retain a hold over the King through the influence of Lady Yarmouth, by then George II's mistress, but John Montagu, 4th Earl of Sandwich and Thomas Pelham-Holles, 1st Duke of Newcastle, combined forces against him, and in 1748, he resigned the ministerial seal and returned to his books and playing cards with the admirable composure that was one of his most striking characteristics. Despite his denials, Chesterfield is speculated to have at least helped to write "Apology for a late Resignation", in a Letter from an English Gentleman to his Friend at The Hague, which ran to four editions in 1748.