Western occultists associate Geburah, the fifth Sephirah, with Mars and grant it dominion over things like warfare and iron. (Those familiar with African Diaspora traditions will also be reminded of Ogou, the hot-tempered ruler of battlefield and forge). This Martial feeling pervades Tarot's 5s. Wherever they show up they point to a conflict in the Querent's life, an ongoing struggle requiring hard work and constant vigilance. When we look into the 5 of Cups we see the emotional toll this war has taken on the Querent and on others caught up in the battle.
Crowley called the 5 of Cups "Disappointment" and likened it to "disturbance, just when least expected, in a time of ease." For him water's placid nature was inherently at odds with Geburah's fiery energy. The 5 of Cups could at best be a goad which rouses the Querent from slumber. No matter how hard we try to avoid it, sooner or later we must wake up and smell the coffee. Often the 5 of Cups holds that bitter brew, served alongside a bill for last night's revels. Given his life history it's not surprising the Great Beast most often encountered the 5 of Cups in that capacity. (Combined with the 7 of Cups, the Devil or other cards associated with addiction, this cosmic hangover may be literal. The Querent will have to decide whether it will be rock bottom or just another step on the way down).
Waite saw this as a card of blended pleasures: in the image drawn by Pamela Coleman Smith for the Rider-Waite deck, the cloaked figure stands beside three spilt cups but two remain standing. The Querent's losses are painful, but they are not total: brooding on what was will be less fruitful than looking toward what is to come. This is not the inescapable end of Death nor the utter ruin of the 10 of Swords. The 5 of Cups calls us to cherish what remains and to move on with what and who we have. It reminds us that all pleasures are transient and all joys mixed. Yet it reminds us also this makes them no less joyful nor precious.
Cups are inherently forgiving: the sea refuses no river and water flows into every available space. This easy-going acceptance cannot last long under the warrior's pitiless scrutiny. When the 5 of Cups shows up in a reading, the Querent will pay the price of misplaced trust. The heat is on, and fair-weather friends will consider you less important than air conditioning. This is generally not so life-altering as the Tower (another Martial card) but even small betrayals hurt. And if the Querent allows 5's energetic nature the day, a little present pain will save much greater hurt down the road. With this card, as with the other 5s, returning to the status quo is not an option: the watery temptation to inaction is here more hazard than help.