Roland's closest childhood friend and fellow apprentice gunslinger in Gilead. Cuthbert is the quick-witted, talkative one of the trio - sharper-spoken than Roland and quicker to a joke, with a ready grin he can produce even in situations no one else in the room can find anything funny about. He trains alongside Roland under Cort, present for the small everyday cruelties of their apprenticeship and the larger crises that shape them: the master hawkman David's training, the cook Hax's treason, and the unprecedented early test Roland is driven to demand for his coming of age. Loyal, sharp, and unsentimental about the kind of company gunslingers tend to keep, Cuthbert is the friend Roland trusts soonest and longest.

A big, blond, stolid young man from Gilead and one of Roland's closest friends, travelling under the alias Richard Stockworth during the Mejis expedition. Alain possesses the touch - a psychic sensitivity that gives him premonitions and an awareness of what others around him are thinking and feeling. Calm and diplomatic by temperament, he is the natural mediator between Roland and Cuthbert when their tempers collide, and an unfussily capable shot in a tradition that prizes the showier kind of capability above all else.

A heroin addict from 1987 New York, drawn into Mid-World through one of the doors on the beach. Quick-witted and irreverent, Eddie has a gift for defusing tension through humour that masks a deep well of courage. He becomes one of Roland's most capable and loyal companions.

A civil rights activist from 1964 New York with dissociative identity disorder, drawn into Mid-World through one of the doors on the beach. Her two identities - the composed Odetta Holmes and the volatile, dangerous Detta Walker - must find a way to coexist. A wheelchair user who lost her legs below the knee in a subway accident, she becomes one of Roland's most formidable companions.

A boy from New York who finds himself drawn into Mid-World, where he becomes a companion to Roland and his ka-tet. Perceptive and brave beyond his years, Jake possesses a low-level psychic ability and bonds deeply with the billy-bumbler Oy.

A young gunslinger of Gilead and one of Roland's ka-mates, known as 'Silent Jamie' or 'Jamie Red-Hand' for his permanently red hand. Quiet and taciturn but an excellent tracker and sharp thinker. Steven Deschain sends him with Roland to investigate the skin-man in Debaria. He prefers the bow and bah over guns.

The weapons master of Gilead who trained Roland and his generation of gunslingers. Brutal, demanding, and deeply traditional, Cort tested each apprentice with a formal combat trial that would either earn them their guns or exile them. Roland defeated him at an unusually young age - the youngest ever to do so - using a trained hawk named David. Cort appears primarily in the Wizard and Glass flashbacks and in Roland's memories throughout the series.

Roland's father, a gunslinger of the twenty-ninth generation descended from Arthur of Eld. He sends Roland, Cuthbert, and Alain to Mejis to keep them safe from the growing conflict with John Farson, while also tasking them with counting the Barony's resources. He wrote the letter of introduction that the boys carry. A grave, wise man who understands the political situation better than most, he is mentioned throughout Roland's flashback as a guiding influence.