Few games lend themselves to philosophical metaphors like the game of chess.
The two armies, one dark and one bright, have been battling each other for millennia in endless struggle. An abstract fight of mathematical perfection, as mankind’s “terrible love of war” is inscribed within an orthogonal grid which is only superficially reassuring.
The chessboard hides in fact an impossible combinatory vertigo, an infinity of variations. One should not be fooled by the apparent simplicity of the scheme (the estimate of all possible games is a staggering number), and remember that famous Pharaoh who, upon accepting to pay a grain of wheat on the first square and to double the number of grains on the following squares, found himself ruined.

The battle of 32 pieces on the 64 squares inspired, aside from the obvious martial allegories, several poems tracing the analogy between the chessboard and the Universe itself, and between the pawns and human condition.
The most ancient and famous is one of Omar Khayyám‘s quatrains:

Tis all a Chequer-board of nights and days
Where Destiny with men for Pieces plays:
Hither and thither moves, and mates, and slays,
And one by one back in the closet lays.

This idea of God moving men over the chessboard as he pleases might look somewhat disquieting, but Jorge Luis Borges multiplied it into an infinite regress, asking if God himself might be an unknowing piece on a larger chessboard:

Weakling king,  slanting bishop, relentless
Queen, direct rook and cunning pawn
Seek and wage their armed battle
Across the black and white of the field.

They know not that the player’s notorious
Hand governs their destiny,
They know not that a rigor adamantine
Subjects their will and rules their day.

The player also is a prisoner
(The saying  is Omar’s) of another board
Of black nights and of white days.

God moves the player, and he, the piece.
Which god behind God begets the plot
Of dust and time and dream and agonies?

This cosmic game is of course all about free will, but is also part of the wider context of memento mori and of Death being  the Great Leveler. Whether we are Kings or Bishops, rooks or simple pawns; whether we fight for the White or Black side; whether our army wins or loses — the true outcome of the battle is already set. We will all end up being put back in the box with all other pieces, down in “time’s common grave“.

It comes as no surprise, then, that Death many times sat at the chessboard before Man.

In the oldest representations, the skeleton was depicted as cruel and dangerous, ready to violently clutch the unsuspecting bystander; but by the late Middle Ages, with the birth of the Danse Macabre (and possibly with the influence of the haunting but not malevolent Breton figure of Ankou) the skeleton had become unarmed and peaceful, even prone to dancing, in a carnival feast which, while reminding the viewer of his inevitable fate, also had an exorcistic quality.

That Death might be willing to allow Man a game of chess, therefore, is connected with a more positive idea in respect to previous iconographic themes (Triumph of Death, Last Judgement, the Three Kings, etc.). But it goes further than that: the very fact that the Reaper could now be challenged, suggests the beginning of Renaissance thought.

In fact, in depictions of Death playing chess, just like in the Danse Macabre, there are no

allusions or symbols directly pointing to the apocalyptic presence of religion, nor to the necessity of its rituals; for instance, there are no elements suggesting the need of receiving, in the final act, the extreme confort of a priest or the absolution as a viaticum for the next world, which would stress the feeling of impotence of man. Portrayed in the Danse Macabre is a man who sees himself as a part of the world, who acknowledges his being the maker of change in personal and social reality, who is inscribed in historical perspective.

(A. Tanfoglio, Lo spettacolo della morte… Quaderni di estetica e mimesi del bello nell’arte macabra in Europa, Vol. 4, 1985)

The man making his moves against Death was no more a Medieval man, but a modern one.
Later on, the Devil himself was destined to be beat at the game: according to the legend, Sixteenth Century chess master Paolo Boi from Syracuse played a game against a mysterious stranger, who left horrified when on the chessboard the pieces formed the shape of a cross…

But what is probably the most interesting episode happened in recent times, in 1985.
A Dr. Wolfgang Eisenbeiss and an aquaintance decided to arrange a very peculiar match: it was to be played between two great chess masters, one living and one dead.
The execution of the game would be made possible thanks to Robert Rollans, a “trustworthy” medium with no knowledge of chess (so as not to influence the outcome).
The odd party soon found a living player who was willing to try the experiment, chess grandmaster Viktor Korchnoi; contacting the challenger proved to be a little more difficult, but on June 15 the spirit of Géza Maróczy, who had died more than 30 years before on May 29, 1951, agreed to pick up the challenge.
Comunicating the moves between the two adversaries, through the psychic’s automatic writing, also took more time than expected. The game lasted 7 years and 8 months, until the Maróczy’s ghost eventually gave up, after 47 moves.

This “supernatural” game shows that the symbolic value of chess survived through the centuries.
One of the most ancient games is still providing inspiration for human creativity, from literature (Carroll’s Through the Looking Glass was built upon a chess enigma) to painting, from sculpture to modern so-called mysteries (how could chess not play a part in Rennes-le-Château mythology?).
From time to time, the 64 squares have been used as an emblem of seduction and flirtation, of political challenges, or of the great battle between the White and the Black, a battle going on within ourselves, on the chessboard of our soul.

It is ultimately an ambiguous, dual fascination.
The chessboard provides a finite, clear, rationalist battlefield. It shows life as a series of strategical decisions, of rules and predictable movements. We fancy a game with intrinsic accuracy and logic.
And yet every game is uncertain, and there’s always the possibility that the true “endgame” will suddenly catch us off guard, as it did with the Pharaoh:

CLOV (fixed gaze, tonelessly):
Finished, it’s finished, nearly finished, it must be nearly finished.
(Pause.)
Grain upon grain, one by one, and one day, suddenly, there’s a heap, a little heap, the impossible heap.

(Thanks, Mauro!)