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| “ | I am so sorry. | „ |
| ~ The Sorrowful Men before killing their victims. |
| “ | Back in Qarth, the warlock Pyat Pree had sent a Sorrowful Man after her to avenge the Undying she'd burn in their House of Dust. Warlocks never forgot a wrong and the Sorrowful Men never failed to kill. | „ |
| ~ Daenerys Targaryen on the Sorrowful Man's attempt to kill her. |
The Sorrowful Men are minor antagonists in the A Song of Ice and Fire novel series. While much of their history isn't known in full detail, and like the Faceless Men of Braavos, they are an ancient guild of assassins that reside in Qarth.
In the main series, a Sorrowful Man attempted to assassinate Daenerys Targaryen with a poisonous Manticore insect in response to the destruction of the House of the Undying and the death of the Undying Ones, the chief warlocks of Qarth. The assassin's assassination attempt was thwarted, however, by Arstan Whitebeard (actually Ser Barristan Selmy) while the Sorrowful Man escaped.
History[]
While not fully explored, the Sorrowful Men have been active since ancient times and are known to whisper to their victims "I am so sorry" before killing them, and they were noted by Daenerys of never failing in their assassinations. It is implied that the Sorrowful Men are known to pose as different people living in Qarth, such as market merchants.
Ever since Drogon, one of the three dragons hatched by Daenerys Targaryen, killed the Undying Ones to protect his mother, while also destroying the House of the Undying, which in turned caused the Qartheen warlocks' magic to leak out onto all of Qarth and its lands, the Qartheen became cold and hostile towards Daenerys overtime, as because of Drogon's actions, it reminded them of the threat posed by dragons; while the Qartheen Elite stopped giving gifts to Daenerys, many wanted her out of the city immediately with the Tourmaline Brotherhood calling for her expulsion while the Ancient Guild of Spicers openly called for her death.
Having been warned of this by Xaro Xhoan Daxos, who also warned her that the warlocks are gathering in great power to take revenge on her, Daenerys realized that she had to leave immediately. While strolling along a Qartheen port to look for a ship that will take her out of Qarth, a Sorrowful Man posing as a merchant gifts her with a beautiful jeweled box carved out of wood with its lid made of mother-of-pearl and inlaid with jasper and chalcedony. Thanking the "merchant" for the gift, Daenerys opens the box and finds what appears to be a jeweled scarab. As she reached inside to use it to buy passage, she failed to hear the man whisper to her, "I am so sorry,".
Soon after Daenerys reached inside the box, the scarab suddenly leapt out of the container, which caused mayhem in the port as many Qartheen screamed and shout as they hastily scrambled to get away. It turns out, the jeweled scarab is actually a deadly manticore, a deadly scorpion-like insect from the islands of the Jade Sea, whose sting and venom is fatally poisonous. Before it could kill Daenerys with its bite, Ser Barristan Selmy, who had assumed the identity of Arstan Whitebeard, and who had been following her with Strong Belwas, swiftly knocked the manticore off her hands with his staff, killing it.
While returning to Pentos with her escorts, Daenerys remembers the attempt on her life back in Qarth and believes that Pyat Pree had sent the Sorrowful Man to kill her to avenge the Undying Ones, noting to herself that the Qartheen Warlocks never forget a wrong while the Sorrowful Men always succeed in their kills.
Trivia[]
- Though Daenerys believed that Pyat Pree is the one who had sent the Sorrowful Man after her, however, it is clearly unknown on who had ordered her assassination, as many factions in Qarth, such as the Ancient Guild of Spicers, wanted her dead, but because Pyat Pree seeks to avenge the Undying Ones, it's strongly implied that he is the one who had ordered Daenerys' assassination.
- Despite the Sorrowful Men's reputation of never failing in their kills, however, given Ser Barristan Selmy's swift intervention, this makes this attempt on Daenerys' life the first (and possibly the only) time where a Sorrowful Man failed to make a kill.
- In Game of Thrones, the televised adaptation of the A Song of Ice and Fire series, the Sorrowful Man who tried to kill Daenerys with a manticore was cut from the show, being replaced with a child agent of the Qartheen Warlocks. However, she also used a manticore to attempt to murder Daenerys and (like the Sorrowful Man) thwarted by Ser Barristan and being forced to escape.

