(Note: this is a collection of the meanings attributed to the cards by some occultists in the past centuries. It does not reflect my own study or opinion of the cards. It is only meant as a quick comparative reference as I develop my own take.)

Paul Foster Case (and Ann Davies)

The time period is the first decanate of Aquarius, from January 20 to 29, under the rulers hip of Saturn and Uranus.
Well-Dignified: the decision is adve rse to the Querent in any matter of a material nature. In spiritual affairs this card portends apparent troubles which work out ultimately to good result. Thus this Key is one of trouble and anxiety, but rightly comprehended can be the turning point for positive good .
Ill-Dignified: the troubles are intensified and are probably due to the Querent’s own lack of understanding of the true nature of the situation. If the question is one of speculation, the Querent is likely to be disappointed due to his own desire to get something for nothing, to over-reach somebody else,
or to get rich quick.
Keyword: Defeat.
(From the Oracle of Tarot Course)

A. E. Waite

A disdainful man looks after two retreating and dejected figures. Their swords lie upon the ground. He carries two others on his left shoulder, and a third sword is in his right hand, point to earth. He is the master in possession of the field. Divinatory Meanings: Degradation, destruction, revocation, infamy, dishonour, loss, with the variants and analogues of these. Reversed: The same; burial and obsequies.
(From The Pictorial Key to the Tarot)

Aleister Crowley

The Five of Swords is similarly [to the other fives] troublesome; the card is called Defeat. There has been insufficient power to maintain the armed peace of the Four. The quarrel has actually broken out. This must mean defeat, for the original idea of the Sword was a manifestation of the result of the love between the Wand and the Cup. It is because the birth had to express itself in the duality of the Sword and the Disk that the nature of each appears so imperfect.

[…]

Geburah, as always, produces disruption; but as Venus here rules Aquarius, weakness rather than excess of strength seems the cause of disaster. The intellect has been enfeebled by sentiment. The defeat is due to pacifism. Treachery also may be implied.

The hilts of the swords form the inverted pentagram, always a symbol of somewhat sinister tendency. Here matters are even worse; none of the hilts resembles any of the others, and their blades are crooked or broken. They give the impression of drooping; only the lowest of the swords points upwards, and this is the least effective of the weapons. The rose of the previous card has been altogether disintegrated.

The historian is happy to observe two perfect illustrations of the mode of this card and the last in the birth of the Aeon of (1) Osiris, (2) Horus. He will note the decay of such Virtue as characterized Sparta and Rome, ending in the establishment of the Pax Romana. As Virtue declined, corruption disintegrated the Empire from within. Epicene cults, such as those of Dionysus (in its degraded form), of Attis, of Adonis, of Cybele, the false Demeter and the prostituted Isis, replaced the sterner rites of the true Solar-Phallic gods; until finally (the masters having lost the respect, and so the control, of the plebs, native and alien) the lowest of all the slave-cults, dressed up in the fables of the vilest of the parasitic races, swept over the known world, and drenched it in foul darkness for five hundred years. He will delight to draw close parallels with the cognate phenomena displayed before the present generation.
(From The Book of Thoth)

Golden Dawn’s Book T

TWO Rayed Angelic Hands each holding two swords nearly upright, but falling apart of each other, right and left of the card. A third hand holds a sword upright in the centre as though it had disunited them. The petals of the rose, which in the four had been reinstated in the centre, are torn asunder and falling. Above and below are Venus and Aquarius for Decan.

Contest finished and decided against the person; failure, defeat, anxiety, trouble, poverty, avarice, grieving after gain, laborious, unresting; loss and vileness of nature; malicious, slanderous, lying, spiteful and tale-bearing. A busybody and separator of friends, hating to see peace and love between others. Cruel, yet cowardly, thankless and unreliable. Clever and quick in thought and speech.
Feelings of pity easily roused, but unenduring.

Geburah of HB:V (Defeat, loss, malice, spite, slander, evil-speaking).
Herein the Angels HB:ANYAL and HB:Cha’aMYH bear rule.

Etteilla

Loss
Upright. This card, as far as the medicine of the spirit is concerned, means, in its natural position: Loss, Alteration, Discredit, Degradation, Perdition, Decay, Destruction, Deterioration, Deterioration, Diminution, Depression, Diminution, Damage, Failure, Prejudice, Blemish, Torts, Avarice, Decline of business, Failure, Disadvantage, Devastation, Dilapidation, Dissipation, Injury, Disgrace, Reversal, Reversal of fortune, Ruin. – Defeat – Debauchery, Disgrace, Dishonor, Infamy, Ignominy, Affront, Ugliness, Difformity, Humiliation. – Theft, Thievery, Rape, Plagiarism, Abduction, Filthy, Horrible. – Infamy, Corruption, Profligacy, Seduction, Libertinism.
Reversed. Mourning, Abasement, Affliction, Sadness, Grief, Pain of spirit, Funeral pump, Burial, Funeral, Inhumation, Burial.

MQS