The Wishing Game

The novel’s non-villainous antagonist, Jack Masterson, is known as the most famous children’s literature author, having penned 65 books for his Clock Island series. The novel doesn’t reveal whether Jack has any blood relatives, but he considers Hugo his son and Lucy, Dustin, Andre, and Melanie his honorary children (though the text implies that Lucy and Hugo’s relationship will grow past friendship after the novel’s ending, possibly making her more accurately Jack’s daughter-in-law). As an older man, Jack “wear[s] his […] uniform of rumpled trousers, a light blue button-down shirt with a coffee stain on it, and a baggy cardigan starting to unravel at the seams” (260). He lives on a private island, called Clock Island, off Portland, Maine, which he has fashioned to mimic locations in his book series.

Jack’s troubled childhood, with an abusive father who drank heavily, inspired him to write about Clock Island. Even as a child, Jack took comfort in the concept of a clock as a location rather than simply a marker of time because it represented safety when all else was beyond his control. Jack truly loves children, in complete contrast to his father, and is protective of them, which is why Hugo likens him to a bear: “His own father was an absolute tyrant. Our Jack’s a teddy bear until you show him a child in trouble, and then you’ll see a teddy bear turn into a grizzly” (200). As well-intentioned as he may be when he tries to protect children, however, his desire to do so is what involved him in the tragedy of Autumn Hillard’s death and led to his six-year period of depression.

While Jack has always shown a deep affection and nurturing spirit toward children, his desire to be a father (whether biological or adoptive) was hampered by his being gay and his practical fears about his public image. The novel illustrates how preconceptions of gender and sexual orientation impeded Jack’s pursuit of adoption (See: Background): “Even now, it’s hard for a single man, especially a single gay man, to adopt children. Imagine how impossible it seemed thirty years ago when I was young enough to do something so brave and stupid as try to be a father on my own” (227). In a way, his decision to conduct the Clock Island contest is an act of fatherly love toward both Hugo and the four children who fled challenging situations and came to his island over the years. He grants them five days to enjoy their most childlike fantasies, makes them take part in games and challenges that they enjoy, and grants their wishes according to what they really need. In addition, he forces them to mature, especially in Lucy’s case. Although the novel never reveals what fears he makes the other contestants face, Jack’s decision to arrange for Lucy and Angie to meet and talk until they resolve their issues is a hallmark parenting style common to most parents whose children quarrel. Jack finally realizes his desire for children of his own: At the novel’s end, Hugo chooses to stay on Clock Island, and Lucy and Christopher have agreed to move in with Jack permanently.

Lucy met Hugo Reese, her burgeoning love interest, when she was 13 years old. Hugo works as an artist and is Jack’s exclusive book cover illustrator, though he created his own picture book, Davey’s Dreamworld, for which he earned a Caldecott Medal. While Jack considers Hugo his son, Hugo has a family in the United Kingdom: an unnamed mother and a younger brother named David, or Davey, but Davey died of heart trouble related to Down syndrome when Hugo was 23. Although Hugo in younger years dressed and styled himself in what Lucy considered rock star fashion, Hugo as an adult is described as “midthirties, strong jaw, intelligent and intense blue eyes behind a pair of black-framed glasses. […] He was handsome, very handsome. Almost distinguished. More professor than rock star these days” (104).

Perhaps more than any other character, Hugo had his entire life upended by Jack’s whimsical nature, for better and worse. To varying degrees, Hugo owes his successful career as an artist and illustrator to Jack’s novels, specifically to Jack’s fake contest to find a new illustrator since he didn’t like the one his publishing company had assigned to him. Hugo was only 21 at the time and was only meant to win a cash prize at the end of the contest. As Jack often did, however, he turned it into an opportunity, and what began as a professional relationship between an older artist and one fresh out of adolescence became more meaningful, as Jack assumed a father-figure role for Hugo. Their relationship turned familial, especially when Davey died. Jack’s support then was crucial to keeping Hugo afloat, as he explains in this excerpt: “After Davey was gone, I went off the rails. Booze, drugs, the works. […] I was flirting with death back then. Jack saw the signs, staged an intervention” (161). Jack’s decision to help Hugo then not only paved the way for Hugo’s recovery but also eventually trapped Hugo on the island with him.

Although Hugo has an acerbic personality, and his sarcasm is an innate feature of his demeanor, he’s loyal to a fault to those he loves and believes in returning the favors he receives. As Jack sunk into melancholy after Autumn’s death, Hugo’s conflicting feelings about leaving Jack behind cost him an intended marriage to Piper, an art career outside of Clock Island, and six years of his life to act as Jack’s caretaker. Even so, he genuinely tells Lucy that “losing [his] brother was the worst thing that ever happened to [him], but Jack was the best” (162). Hugo doesn’t resent the sacrifices he made for Jack; his fear stems from his love for Jack, and once Jack seems content once again, Hugo’s dilemma resolves: He chooses to stay on Clock Island not as Jack’s caretaker but as his son.

A secondary character, Christopher Lamb is Lucy’s main motivation to participate in the Clock Island contest. Christopher has lived in foster care since the death of his parents. With no other known relative to claim him, he hopes that Lucy, whom he met at Redwood Primary School while a student there, can adopt him. He’s seven years old and is described as “a slight wide-eyed black-haired boy” (12) who likes to keep his hair fluffy. Christopher has a history of nightmares and a devastating fear of ringing phones after discovering his parents lying dead in bed one morning as his mother’s boss kept calling. An avid reader of Jack’s books, Christopher writes letters to both his deceased parents and (without Lucy’s knowledge) to Jack himself. Supported by his love for Lucy and by Jack’s encouragement, Christopher eventually overcomes his fear of phones at the novel’s end and becomes Lucy’s adopted son and Jack’s honorary grandson.

Andre Watkins, Dustin Gardner, and Melanie Evans are all secondary characters who can be loosely considered antagonists toward Lucy because they actively try to win Jack’s contest themselves. Andre is a successful lawyer, Dustin is a doctor, and Melanie is a bookshop owner. Although Andre and Melanie eventually become friends with Lucy and compete with her honestly, Dustin tries to convince her to cheat the system and split the winnings, which immediately disqualifies him from the competition. All three contestants, in their younger years, ran away from difficult family situations to visit Jack on his island: Andre for racist bullying, Dustin for fear of coming out to his parents, and Melanie for having to move to a new town and having no friends. Each competitor faces what appears to be an insurmountable situation that is just as dire, if not more so, than Lucy’s: Andre’s dying father needs a new kidney, Melanie has a failing bookstore, and Dustin is being crushed by student loans. Although the competition pits them against one another, the text highlights that (at least in Andre and Melanie’s case) they’re good people and recognizes that they’re all worthy of winning. In fact, they sincerely wish each other good luck. Although none of them do win, Jack grants the wish of each of them in the end.