When Trickster's Choice opens, the Copper Isles is ruled by an insane king whose heirs include an obese, pleasure-seeking man, a five-year-old boy, and a scheming princess who is determined to seize power through her equally power-hungry husband.

Alanna by this time is the Lioness of Pirate's Swoop and Olau, lady knight, King's Champion of Tortall, and a living legend.

Frustrated with her parents, (who refuse to allow her to become a spy), Aly takes her boat, the "Cub", and sails down the coast, but is captured by pirates along the way.

Despite being a pretty girl in a very bad situation, Aly keeps her head, intentionally getting herself bruised and starving herself so that she won't be bought as a sex slave.

However, shortly after Aly's arrival, the Balitang family falls out of favor with King Oron of the Copper Isles, and are forced to sell most of their slaves and household goods.

The Balitangs are visited by Prince Bronau, a close friend of the family who has also fallen out of favor with the king, and who flirts constantly with Sarai.

During this time, Mithros, (the sun god), and the Great Mother goddess appear to Kyprioth and Aly, demanding why their brother is so far from the seas that they banished him to.

Aly covers up for Kyprioth, remembering the training she received about lying to the gods and managing to fool the two deities by telling only part of the truth.

She also faces relationship troubles with Nawat, who is struggling to find his place in the world of men and puzzled over why she won't mate with him.

Aly soon destroys Topabaw's relationship with the regents through psychological warfare, and he is executed, to be replaced with a far more inexperienced man, Sevmire Ambau.

Finally, Aunt Nuritin is the head of a Luarin conspiracy, which also plots to overthrow the current rulers, but has not yet made a move towards this goal.

Aly also receives help; Daine, her adoptive aunt, gifts her with a collection of creatures called darkings through Tkaa the Basilisk, that agree to spy for the rebellion.

The rebellion's first major act is when a powerful member of the Luarin conspiracy, Duke Nomru, is arrested and sent to Kanodang prison.

However, buried in spy reports and plots, Aly fails to notice Sarai's infatuation with Zaimid Hetnim, a young Carthaki healer, until it is too late.

However, this failure comes with a blessing—the rebellion now turns its attention to Dove, who, as an intelligent and cool-headed young woman, is a far more suitable candidate for the throne.

Aly begins to turn the regents against each other, planting false "proof" that Rubinyan is having an affair, and learns from the darkings that her plot has worked.

Aly tells the rebellion's leaders, including Dove, about her true parentage, then goes on to marry Nawat Crow and becomes pregnant after removing the anti-pregnancy charm, he gave her before mating.

Throughout the series, occasional appearances are made by many of the main characters from other Tortall books, including Alanna the Lioness, Baron George Cooper of Pirate's Swoop, King Jonathan III of Tortall, Myles of Olau, Daine the Wildmage, Numair Salmalín, Keladry of Mindelan, the Graveyard Hag and Tkaa the Basilisk.

Trickster's Choice was published by Random House in 2003, twenty years after Pierce's first book, Alanna: The First Adventure, and was eagerly awaited by her fans.