As the eldest of the Greystone children at age 12, and the only one with any tangible memories of their deceased father, Chess assumes the sobering responsibility of caretaker for his younger siblings. When their mother disappears and he, Emma, and Finn are plunged into danger, he feels, rightly or wrongly, that he must take up the adult mantle and protect them. Unfortunately, the bizarre circumstances and nearly insurmountable obstacles are too much for him, as they would be for any 12-year-old. Chess is torn between being a kid and being the eldest kid, a conflict that robs him of self-confidence when he needs it most. Up until now, he spent his life as the dutiful son, trying to fill his father’s shoes and to protect his mother from her own grief.

As a result, he is ill-prepared to handle the demands of coded letters and mysterious worlds. Chess is further hampered by encroaching puberty, which is especially troublesome when in the presence of Natalie. He finds her popularity intimidating, and he frequently stumbles over his words when he’s around her, although part of his character arc is overcoming his shyness and learning to respond to Natalie with confidence. In a sense, Chess is too old to effectively handle the crisis, and he must rely on his younger siblings to pull him back in time a few years, to the days when he could see the possibilities in the world and not just the limitations.