An often-reproduced painting in a private collection in Brooklyn purports to depict from life, around 1603, Ben Jonson and William Shakespeare playing chess. Bryan Loughrey and Neil Taylor, writing in the Winter, 1983, issue of Shakespeare Quarterly, noted that, “The chess portrait is unusual in that . . . its claims to authenticity rely largely on internal evidence.” They suggested, “One possible explanation is that it is an ‘ideal’ portrait of the two poets . . . painted later in the century.” Whether contemporary with Shakespeare or later, it serves as a fun source for meditating upon Shakespeare and chess.

Since the nineteenth century, chess enthusiasts have convinced themselves that Shakespeare played chess. That painting showing him playing chess with his friend and rival playwright Ben Jonson came to light in 1878, and scholars of chess have studied the painting’s chess board and figured out the state of play. According to that painting, Shakespeare was very good at chess: he seems about to put Jonson in checkmate.

In the mid-1800s, Howard Staunton was living in his native London, and he was a master of chess, winning several tournaments. The standard style of chess pieces now in use was designed and named in his honor. In addition to writing manuals for chess, he also edited the plays of Shakespeare.

In King John, Act II, Scene 1, Queen Eleanor tells Lady Constance, “Out, insolent! Thy bastard shall be king,/That thou mayst be a queen, and check the world.” Staunton declared in a footnote: “It has been doubted whether Shakespeare, who appears to have had cognizance of nearly every sport and pastime of his age, was acquainted with the ancient game of chess; we believe the present passage may be taken to settle the question decisively.” Staunton elaborated, “The allusion is obviously to the queen of the chess board, which, in this country, was invested with those remarkable powers that render her by far the most powerful piece in the game somewhere about the second decade of the sixteenth century.”

Elsewhere in King John, Act III, Scene 1, King Phillip warns King John, “Look to thyself, thou art in jeopardy.” It is the only time in his writings Shakespeare used the word jeopardy, and to chess aficionados, one king is clearly warning the other he is in jeopardy of checkmate.

Still, the basic terms of chess are the basic terms of medieval and Renaissance society: king, queen, bishop, knight, castle. Moreover, words like check, mate, and pawn have multiple meanings, and Shakespeare nearly always used pawn in reference to pawning something. The one exception occurs in King Lear, where in Act I, Scene 1, Kent tells Lear, “My life I never held but as a pawn/To wage against thine enemies.”

Nevertheless, none of it adds up to Shakespeare playing chess. He could have known about the vocabulary and objectives of chess without ever playing it. In his writings, the only explicit mention of chess comes in a stage direction in The Tempest. In Act V, Scene 1, we read: “Here Prospero discovers Ferdinand and Miranda playing at chess.”

As Prospero finds them, Miranda says to Ferdinand, “Sweet Lord, you play me false,” and Ferdinand protests, “No, my dear’st love,/I would not for the world.” She counters, “Yes, for a score of kingdoms you should wrangle,/And I would call it fair play.”

Shakespeare wrote The Tempest around 1611, and the seeds for it were in his Sonnets, published in 1609. In particular, in Sonnet 116. The Tempest explores that sonnet’s opening line, “Let me not to the marriage of true minds/Admit impediments.” Sonnet 116 goes on to say that love “is an ever-fixed mark/That looks on tempests and is never shaken.” Love is “the star to every wand’ring bark,/Whose worth’s unknown, although his height be taken.”

Love’s worth is unknown, even if its height, its tower, is captured: In Troilus and Cressida, Act I, Scene 2, Alexander tells Cressida that Hecuba and Helen are going, “Up to the eastern tower,/Whose height commands as subject all the vale.” A director would be right to understand that what Prospero sees when he walks in on the two lovers playing chess is Ferdinand playfully offering Miranda one of his rooks, by way of saying she has captured his love. The BBC television production from 1980 seems to do just that.

In her clever and amusing Chess for Children (2013), Sabrina Chevannes explained, “Chess is a battle game between two armies—the white and black armies. They have to fight against each other in order to trap the other army’s king and take over their kingdom.” In The Tempest, chess seems to stand in for the battle of the sexes, but in his last history play, written around 1613, Shakespeare can be seen visually suggesting chess as a metaphor for the legal battle in a court of law.

In Henry VIII, Act II, Scene 4, Shakespeare provided detailed stage directions for a pretrial hearing in Blackfriars priory in London. The year is 1527, and on the docket is King Henry’s desire to divorce Queen Catherine of Aragon. To trumpet fanfare, vergers lead in scribes, gentlemen, noblemen, and bishops, including two cardinals. These various dignitaries array themselves symmetrically on either side of the king, and the queen is made to stand opposite him, alone. Again, a director would be right to have the floor of the hall in black and white squares and to line those worthies up like chessmen.

“The tyrant, Harry the Eighth of England,” wrote Edmund Burke in 1790 in his Reflections on the Revolution in France, “when he resolved to rob the abbies [sic], . . . began by setting on foot a commission to examine into the crimes and abuses which prevailed in those communities.” Very true, but Shakespeare’s play avoids all that unpleasantness. Instead, he appears to employ what in chess is an endgame scenario leading to a draw.

In Act V, Scene 3, the king has lost patience with the standoff between two bishops we may imagine as from queenside and kingside. That is, the Bishop of Winchester, a Catholic stalwart for Queen Catherine, has been confronting the Archbishop of Canterbury, a Protestant advisor to King Henry. The king orders them to embrace as brothers, and while, so to speak, each controls his respective squares, neither bishop wins so long as that king looms large.