Simon Cleare

Quick Facts

• Role: PAL officer, mentor-turned-lover to Mickey, biological father to Thomas
• First appearance: As Officer Cleare at the Police Athletic League gym in Mickey’s teens
• Key relationships: Michaela “Mickey” Fitzpatrick, Kacey Fitzpatrick, Thomas Fitzpatrick
• Defining tension: A polished authority figure whose charm masks manipulation, predation, and addiction

Who They Are

At first glance, Simon Cleare is the kind of cop a lonely teenager might idealize: tall, handsome, self-possessed, and serious. As Mickey’s PAL mentor, he’s the first adult to speak to her as if her intellect and potential matter. He becomes her first love, the father of her child, and the person who nudges her toward the police force. But the qualities that initially feel protective—his discipline, culture, and authority—are the very mechanisms he uses to exert control. Simon’s arc is a study in grooming and the mechanics of secrecy, making him central to the novel’s exploration of Secrets and Betrayal. He also embodies corrupted authority: a cop who preys on the girls he’s meant to protect. As both an old wound and a recurring danger, he personifies the drag of The Unescapable Past and the novel’s broader Moral Ambiguity within systems that promise safety while sheltering abuse.

Personality & Traits

Simon cultivates an old-movie charm—gallant, intellectual, a little austere—that doubles as camouflage. His authority gives him access; his polish lowers defenses; his secrecy isolates. The effect is not simply that he lies, but that he reshapes reality for those around him.

• Authoritative, intellectual mentor: Teaches Mickey chess and assigns books and films, positioning himself as a guide whose approval she must earn—an unequal dynamic that blurs into control.
• Charming, gallant veneer: He holds doors, speaks formally, and carries an “old-fashioned” air—style that reads as safety to Mickey but functions as grooming.
• Manipulative and secretive: Demands their romance remain hidden; reframes Kacey’s accusation as drug-fueled delusion; conceals his relapse and new family for over a year.
• Predatory pattern: He has “a reputation” for targeting PAL girls, making Mickey’s experience part of a broader, whispered pattern protected by silence and institutional inertia.
• Addict as narrative tool: Confesses a past addiction to create intimacy and claim insight into Kacey; later relapse exposes that confession as leverage, not accountability.
• Image-conscious: The slick hair and cinematic poise aren’t superficial details—they’re stagecraft that supports his authority and makes his pursuit of vulnerable teens appear respectable.

Character Journey

Simon doesn’t grow so much as he is revealed. In Mickey’s “Then” chapters, he appears as a steady, cultured lifeline who sees her—an antidote to chaos. The illusion fractures when Kacey accuses him of exploiting her; Simon swiftly reframes her claim as unreliable, isolating Mickey from her sister. Fatherhood initially ties him to Mickey and Thomas through scheduled visits and checks, but his sudden disappearance collapses that fragile stability. A chance encounter at McDonald’s shows the truth: he has a new wife and infant. Later, Detective DiPaolo confirms Simon was seen in Kensington buying a large quantity of OxyContin, revealing a relapse and cementing his transformation from protector to liability. He becomes a cautionary emblem of Addiction and Its Consequences: the past he claims to have mastered is the one that masters him, with fallout borne by the very people he was supposed to protect.

Key Relationships

Michaela “Mickey” Fitzpatrick With Mickey, Simon blends mentor, lover, and gatekeeper. He shapes her self-image and career path while teaching her to trust his version of events over her own intuition. His betrayal deepens her distrust, intensifies the rift with Kacey, and hardens her resolve as a single mother navigating a system he once used to intimidate her.

Kacey Fitzpatrick Simon’s relationship with Kacey is exploitation disguised by her vulnerability. When she becomes pregnant, he weaponizes stigma around addiction to undermine her credibility, ensuring no formal complaint and driving a wedge between the sisters that lasts years.

Thomas Fitzpatrick To Thomas, Simon is first a ritual—monthly visits and checks—then a void. His disappearance forces Mickey into precarious financial and emotional terrain, and his later threat to leverage “friends in the system” to take Thomas underscores how easily he turns institutional power against the family he abandoned.

Defining Moments

Simon’s story is a ladder of boundaries crossed—each step masked as care, each reveal exposing the rot beneath.

• Mentorship at the PAL: Singles Mickey out for chess, books, and films. Why it matters: Establishes dependence and admiration within a power imbalance, softening the ethical lines that follow.
• First kiss on the Delaware pier: Moves from mentor to secret lover when Mickey is eighteen. Why it matters: The secrecy cements his control and converts authority into romantic leverage.
• Reframing Kacey’s pregnancy: Persuades Mickey that Kacey’s accusation is delusional. Why it matters: Isolates Mickey from her sister and preserves his image while hiding predation.
• McDonald’s reveal: Mickey and Thomas encounter Simon with his new wife and baby. Why it matters: Provides the painful, concrete explanation for his disappearance and shatters the last of Mickey’s illusions.
• Confirmed relapse: Detective DiPaolo reports Simon buying a large quantity of OxyContin in Kensington. Why it matters: Reorients his narrative from “recovered mentor” to active risk, connecting his personal failures to systemic harm.
• Threatening legal coercion: On the phone, he boasts of “friends in the system” and threatens custody. Why it matters: Exposes his readiness to weaponize institutional power to silence and control.

Essential Quotes

“He was handsome, for another: he had black, combed-back hair, and sideburns just slightly longer than the rest of the male officers, which in 1997 was quite fashionable, and dark eyebrows that inched together minutely when he read something he found particularly interesting. He was tall and well built and had an air about him that felt to me then vaguely old-fashioned, as if he had been dropped in from another time, from an old movie.”

• Analysis: Mickey’s description frames Simon as cinematic—elevated, curated, unreal. The polish doesn’t just attract her; it authorizes him, making his boundary crossings read like romance rather than exploitation.

“You’re beautiful, said Simon. Do you believe that? —Yes, I said. It was the first time in my life that I did.”

• Analysis: This is grooming in its most seductive form: offering identity as a gift. By becoming the first voice to affirm Mickey’s worth, Simon makes his approval foundational—easier to obey than to question.

“I told him that if he failed to send a check within one week I would take him to court, and he told me that I wouldn’t dare, and asked me if I knew how many friends he had in the system, and told me if I took him to court he would take Thomas away from me like this—here he snapped his fingers—and that I was being unreasonable by keeping Thomas enrolled in such an expensive school, anyway. Who did I think I was? he wanted to know. Who did I think we were?”

• Analysis: The mask slips completely. Simon wields institutional connections and class contempt to intimidate Mickey, revealing how his authority extends beyond personal manipulation into systemic coercion.

“You know he’s got a reputation, he says, hesitantly. —Simon? He nods. —I don’t mean to make you feel bad, he says, or to talk out of school. But you’re not the only one. Rumor is there were other PAL kids he targeted. Seems like there was a pattern, but no one ever confessed, or registered a formal complaint.”

• Analysis: The “reputation” functions as an open secret—proof that institutional cultures can absorb predation without redress. The absence of complaints isn’t exoneration; it’s a map of power, fear, and disbelief working as intended.