Cherreads

Chapter 17 - Chapter 17: Sister and Strategy

Three days had passed. The evidence was conclusive.

Jimmy sat in his office above Morrison's butcher shop on September 12th, holding the Birmingham Gazette's morning edition. The article occupied half the front page, authored by a journalist with known connections to Catherine Winters' campaign.

"WEBB'S SECRET MEETINGS: Reform Candidate's Questionable Business Connections"

The story detailed Webb's supposed meeting with "Richard Ashton" at the Crown Hotel, 3 PM today—the exact time, location, and name Jimmy had invented. The article questioned Webb's reform credentials, suggested he was secretly allied with property developers, implied that his progressive platform was performance masking business-as-usual corruption.

Every detail matched the fabricated memo Jimmy had given to Ada three days ago. The memo he'd shared with exactly one person.

The evidence was mathematical. Ada was feeding information to the opposition.

Jimmy read the article twice, searching for alternative explanations that might absolve her. Perhaps she'd discussed the memo with someone else who'd leaked it. Perhaps her residence had been burgled and documents stolen.

Perhaps some elaborate chain of coincidences had resulted in invented information appearing in opposition materials.

But intelligence work didn't allow for comforting delusions. The simplest explanation was usually correct.

Ada had access to the fabricated memo. Ada had connections to Winters' campaign. Ada's ideological sympathies aligned with Winters rather than Webb.

She was the traitor. His closest friend in the Shelby family was actively undermining Tommy's political operations.

Jimmy set down the newspaper, feeling something break inside his chest. This wasn't Billy Kitchen's desperate betrayal to save his son.

This was principled, calculated opposition—Ada choosing her ideals over her family, her beliefs over her loyalty.

Which somehow made it worse.

He pulled out his notebook and updated his investigation file with clinical precision:

EVIDENCE: Sept 12, Birmingham Gazette article

Contains fabricated meeting information

Information shared ONLY with Ada Shelby, Sept 9

No other suspects had access

Conclusion: Ada is confirmed leak source

MOTIVE: Ideological opposition

Believes Winters is better candidate

Opposes Shelby control of government

Acting from principle rather than greed

RECOMMENDATION: Confront privately before reporting to Tommy

Ada deserves explanation opportunity

Family implications require careful handling

Tommy's response will be extreme—exile or worse

Jimmy closed the notebook, mind already calculating next steps. He should report to Tommy immediately—that was his duty as Shelby strategist. But Ada was family, and family deserved some consideration before being destroyed.

He'd confront her privately first. Give her chance to explain, to defend herself, to maybe provide some justification that made this betrayal comprehensible rather than simply devastating.

Then he'd decide what to tell Tommy.

The blood seeping through his ceiling smelled stronger than usual this morning. Morrison must have been processing a particularly large order.

Violence beneath every surface, even conversations that hadn't happened yet.

---

The Reform Club's afternoon session was well-attended—forty or fifty progressives gathered in the main hall, discussing housing policy and worker protections with the earnest intensity of people who believed good arguments could change the world. Jimmy arrived late, slipping into the back row where observation was possible without participation.

Ada sat three rows from the front, leaning forward in her chair, completely engaged with Catherine Winters' presentation about slum clearance and municipal housing construction. She took notes in her neat handwriting, occasionally nodding at particularly strong points.

Jimmy watched her with the detached assessment of an intelligence officer surveilling a target. This was Ada in her natural environment—intellectual activism, progressive politics, belief that reform could happen through democratic process rather than criminal manipulation.

She belonged here in ways she never quite belonged at Shelby family meetings.

Winters finished her presentation to enthusiastic applause. People broke into smaller discussion groups. Ada stood, gathering her materials, then moved toward a man Jimmy didn't recognize—mid-forties, well-dressed, conservative bearing despite being at a progressive gathering.

They spoke for perhaps five minutes. The man's posture suggested authority, control. Ada listened more than talked, occasionally nodding, her expression serious.

The conversation concluded with a handshake. The man departed through a side exit while Ada returned to her discussion group.

Jimmy made mental notes. The unknown man was significant—his bearing screamed government or military background, and his presence at a Reform Club meeting felt deliberately incongruous.

Possible Section D handler? Intelligence officer using Ada without her knowledge?

He'd investigate later. Right now, he needed to follow Ada, to observe her movements before the confrontation that would destroy their friendship.

She left the Reform Club near four o'clock, walking through Birmingham's afternoon smoke toward her residence. Jimmy maintained distance, tracking her through familiar streets while feeling increasingly like the traitor himself.

Surveillance was betrayal's mirror image—watching people who trusted you, documenting their movements, preparing to weaponize their actions against them.

Ada stopped at a bookshop, emerged twenty minutes later with a wrapped package. Stopped again at a tea shop, purchased something through the window.

Normal errands for a woman with intellectual interests and time to spare.

She had no idea she was being watched. No idea that the investigation had concluded. No idea that tonight's conversation would end everything.

Jimmy let her reach her residence before approaching. He needed time to prepare, to organize his thoughts, to decide how to conduct this confrontation without destroying more than necessary.

But some destructions were inevitable. Ada had chosen her path. Now both of them would pay the price.

---

The sun was setting when Jimmy knocked on Ada's door, painting Birmingham's smoke orange and red. She answered with surprised pleasure, still wearing the dress she'd worn to the Reform Club, books under one arm.

"James! Twice in one week. I'm honored."

"We need to talk," Jimmy said. His voice was flat, controlled. "May I come in?"

Something in his tone made her expression shift from pleasure to concern. "Of course. Is something wrong?"

He followed her into the sitting room he'd surveyed days ago while pretending friendship and planning betrayal. The books were still scattered across surfaces, the progressive publications still visible, the photographs of Shelby family still on the mantle—all the evidence of Ada's divided loyalties made physical.

"Tea?" she offered, falling back on hospitality as buffer against whatever was coming.

"No. This isn't a social visit."

Ada set down her books slowly, her intelligence recognizing danger even if she didn't understand its source yet. "What's happened?"

Jimmy pulled out the Birmingham Gazette, setting it on her coffee table. The article about Webb's fabricated meeting with Richard Ashton faced upward, headline visible.

"This appeared this morning. Detailed account of Webb meeting with corrupt businessman. Time, location, name—all specific, all damning." Jimmy watched her face carefully. "Also all completely fabricated."

"I don't understand."

"The meeting doesn't exist. Richard Ashton doesn't exist. I invented the information three days ago as a test—false intelligence shared with one person to identify our leak."

Jimmy kept his voice clinical, emotionless. "I gave that information to you, Ada. Only you. And now it's appeared in opposition materials, weaponized against Webb's campaign."

The color drained from Ada's face. Not guilt, exactly. More like recognition that her secret had been discovered, that the game was over.

"How did you—" she started.

"How did I know?" Jimmy's control cracked slightly. "I've been investigating leaks for weeks. Systematic surveillance, evidence analysis, elimination of suspects. You were the only person with access, sophistication, and connections to opposition campaigns.

I needed definitive proof, so I set a trap. Congratulations—you walked into it perfectly."

Ada was quiet for a long moment, processing this revelation. When she spoke, her voice carried no apology. "Yes. I've been helping Catherine Winters. Providing her with information about Webb's campaign strategy."

The confirmation hit harder than Jimmy expected despite having known the truth for days. Hearing Ada admit the betrayal made it real in ways evidence hadn't.

"Why?" The word came out raw.

"Because Catherine Winters actually cares about Birmingham's poor." Ada's voice strengthened with conviction. "Your Martin Webb is a puppet who'll do whatever Tommy wants. I can't let that happen—not when there's a genuine alternative who'd actually help working families."

"Webb would help working families. That's the entire point of his campaign."

"Webb would help Shelby betting operations and protection rackets while performing progressive politics for the masses." Ada stood, pacing the room with agitated energy. "Don't pretend you don't know what this is, James. You recruited him. You're managing him. You're corrupting a good man to serve Tommy's criminal interests."

"I'm helping a good man win an election so he can actually accomplish reform instead of losing to Lawrence Blackwood's old money corruption."

"By making him a gangster's puppet?" Ada's voice rose. "By ensuring Birmingham's government is controlled by the same family that runs protection rackets and illegal gambling? How is that better than Blackwood?"

Jimmy felt his own anger rising to match hers. "Because the Shelbys actually help working families when legitimate government fails them. Because Tommy's justice works when police justice doesn't. Because sometimes criminal power serves people better than corrupt legitimacy."

"That's rationalization." Ada faced him directly. "You've convinced yourself that manipulating elections and installing puppets is somehow noble because you're smarter than everyone else and know what's really best for Birmingham."

"I'm doing what actually works instead of what feels morally pure while accomplishing nothing."

"You're betraying democratic principles because you've decided your strategic brilliance matters more than people's right to make their own choices."

Ada's words cut like knives. "You manipulated Webb. You're using him. And you've apparently been manipulating me too—surveillance, false information, treating me like an enemy operative instead of family."

"You ARE an enemy operative." Jimmy's control shattered completely. "You're committing treason against the family. Tommy will exile you when he finds out. Possibly worse. You're betraying everyone who cares about you because your principles matter more than their trust."

"My principles matter more than blind loyalty to criminal corruption," Ada shot back. "I love this family, but I won't help Tommy control Birmingham's government. Someone has to stand for what's actually right instead of what's strategically advantageous."

They faced each other across Ada's sitting room, both breathing hard, both wounded and angry and convinced of their own righteousness.

"You're naive," Jimmy said finally. "You think genuine reform can happen through democratic process, that good intentions and correct principles are enough to change power structures. But Birmingham doesn't work that way.

The Blackwoods and their allies control legitimate channels. The only way to actually help working families is by working within the reality of who has power."

"And you're cynical," Ada countered. "You've decided that because the system is corrupt, everyone must become corrupt to function within it. That there's no difference between criminal manipulation for good purposes and criminal manipulation for bad ones.

That the ends justify any means as long as you're clever enough to rationalize them."

"The ends DO justify the means when the alternative is Lawrence Blackwood exploiting working families for another generation."

"No, James. They don't." Ada's voice broke slightly. "The means become the ends. You corrupt Webb to fight corruption and create another corrupt politician. You manipulate elections to protect democracy and destroy the democratic principle.

You betray everything you claim to serve through the very methods you use to serve it."

Jimmy had no response to that. The argument was too close to his own midnight doubts, the questions he asked himself when rationalization became harder.

"So you helped Winters," he said. "Gave her Webb's strategy, his positions, his vulnerabilities. Because your principles demanded it."

"Because someone had to." Ada's conviction was absolute. "I couldn't stand by and watch the family corrupt another institution. I couldn't let Tommy buy a seat on the city council without opposition. Yes, I helped Winters. I'd do it again. My conscience is clear."

"Your conscience is clear because you've convinced yourself that principle matters more than loyalty. That your individual moral judgment supersedes family obligations."

Jimmy felt exhausted suddenly. "Tommy will never forgive this. When I tell him—and I have to tell him—he'll exile you. Cut you off from the family completely. Is that worth your clear conscience?"

"Better exile with integrity than belonging without it."

"Easy to say before you're actually exiled."

"I've made my choice, James. Now you make yours." Ada met his eyes directly. "You'll report me to Tommy because you're loyal. I'm helping Winters because I'm principled. We're both doing what we think is right. Neither of us will convince the other we're wrong."

The truth of that statement settled over them both. This argument had no resolution, no compromise, no third option that satisfied both positions.

"You used to understand principle," Ada said quietly. "Before you became Tommy's creature. You used to believe that how you achieved goals mattered as much as achieving them. What happened to that person?"

"He learned that principles without power accomplish nothing. That intelligence without pragmatism is just intellectual masturbation."

Jimmy stood, preparing to leave. "I'll report to Tommy tomorrow. You have one night to decide how to handle this. If I were you, I'd run. Because Tommy's response won't be exile. It'll be worse."

"I'm not running." Ada's voice was steady despite visible fear. "I acted on principle. I'll face consequences with the same principle. Tell Tommy whatever you need to tell him. I stand by my choices."

Jimmy walked to the door, then paused. "I thought you were my friend."

"I am your friend. That's why I'm disappointed." Ada's expression carried genuine sadness. "You're brilliant, James. Maybe the smartest person I know. But you've used that brilliance to justify becoming exactly what you once opposed.

You've convinced yourself that manipulation is strategy, that corruption is pragmatism, that betraying principles is somehow serving them. I help Winters because I see what you're becoming and refuse to enable it."

"And what am I becoming?"

"Tommy. But worse, because you dress your ruthlessness in intellectual justification." Ada smiled sadly. "At least Tommy's honest about what he is. You've convinced yourself you're better because you use a fountain pen instead of a gun.

But you're treating people like chess pieces just the same. Maybe more cruelly, because they never realize they're being played."

Jimmy left without responding, walking out into Birmingham's evening with Ada's words following him like ghosts. The confrontation had resolved nothing except confirming what he'd already known—Ada was the traitor, she wasn't sorry, and now he had to decide what to do about it.

The walk back to Small Heath felt longer than usual. Every step carried the weight of impossible choices—betray Ada to Tommy and destroy her, or protect her and betray Tommy's trust.

Family or duty. Loyalty or principle. Intelligence or empathy.

He'd spent three months proving that intelligence could triumph over violence. Now he was discovering that some problems had no intelligent solution—only choices between different kinds of betrayal.

---

The Shelby betting shop was closed when Jimmy arrived near ten o'clock, most operations shut down for the night. But light showed in Tommy's office, and Polly sat in the main room with whiskey and cigarettes, looking like she'd been waiting.

"You confronted her," Polly said. Not a question.

Jimmy stopped in the doorway. "How did you know?"

"Because I'm not blind, and neither are you. Ada's been the traitor since the beginning. Took you three weeks to confirm what I knew months ago."

Polly poured a second glass of whiskey, gestured for Jimmy to sit. "Sit down. You look like you're about to collapse."

He sat, accepting the whiskey gratefully. "You knew Ada was helping Winters?"

"I suspected. Then I observed. Then I knew." Polly lit a fresh cigarette. "My niece isn't subtle when she's passionate about something. She believes in Winters' reform platform. Opposes Shelby involvement in government. Has connections to opposition organizers. The math wasn't complicated."

"Why didn't you tell Tommy?"

"Because Ada's family. Because her heart's in the right place even if her choices are destructive. Because I hoped she'd stop before forcing choices we'd all regret."

Polly studied Jimmy through smoke. "You're going to report her tomorrow."

"I have to. She's actively undermining operations. Tommy ordered me to find the traitor."

"And now you've found her. Congratulations—you've proven your loyalty by identifying your closest friend as a security threat." Polly's tone carried no judgment, just statement of fact. "What did she say when you confronted her?"

"That she acted on principle. That she couldn't let the family corrupt government. That Catherine Winters is genuinely better for Birmingham than Webb."

Jimmy drank his whiskey, welcoming the burn. "She's not apologetic. Said she'd do it again."

"Of course she would. Ada's nothing if not principled." Polly considered this. "She's also not wrong, you know. Winters would be better for Birmingham's poor than a Shelby puppet. Ada's choosing the morally correct position."

"She's committing treason against family."

"Both things can be true." Polly refilled their glasses. "That's what makes this complicated instead of simple. If Ada was selling information for money or helping enemies out of spite, the choice would be easy.

But she's acting from genuine belief that Shelby control of government is wrong. That's principled betrayal—the most difficult kind to address."

Jimmy set down his glass. "What would you do?"

"I'd ask myself which matters more—Tommy's political ambitions or Ada's conscience. Family unity or individual principle. Loyalty to organization or loyalty to person."

Polly's gaze was sharp, assessing. "Those are the real questions, aren't they? Not whether Ada betrayed us—she clearly did—but whether that betrayal is unforgivable."

"Tommy will think it is."

"Tommy will want her exiled or worse. Arthur will demand blood. John will follow Tommy's lead." Polly tapped ash into a tray. "Which leaves you as the person who decides whether Ada pays the full price for her principles or whether she gets protected from consequences."

"I can't protect her from this."

"You're Tommy's strategist. You can protect anyone if you're clever enough." Polly leaned forward. "The question is whether you will. Whether Ada's friendship matters more than your position.

Whether you're still capable of choosing person over principle, or whether you've become so committed to strategic thinking that humans are just variables to be managed."

Jimmy felt the accusation like physical blow. "That's not fair."

"It's completely fair. You've spent three months treating people like problems to be solved—recruiting Webb through manipulation, using Ada's networks while investigating her for treason, teaching strategic deception as though it's a virtue."

Polly's voice was sharp but not unkind. "Intelligence without empathy is cruelty, Jimmy. You're becoming very good at intelligence. The question is whether you're losing your empathy in the process."

They sat in silence for a long moment, whiskey and cigarette smoke filling the space between them.

"What would you do?" Jimmy asked again.

"I'd remember that family is supposed to matter more than business. That Ada's crime is loving Birmingham more than loving power. That sometimes the right choice costs everything you've worked to build."

Polly stood, preparing to leave. "But I'm not you. You have to make your own choice. Just make sure you can live with the person that choice requires you to become."

She left him alone in the empty betting shop, surrounded by the evidence of everything he'd built—his position as strategist, his integration into the family, his reputation for solving impossible problems through intelligence rather than force.

All of it built on choosing duty over friendship, loyalty over principle, strategic advantage over human connection.

Ada was right. He was becoming Tommy. Or possibly something worse—Tommy with intellectual justification for his ruthlessness.

Jimmy pulled out his notebook, staring at the investigation file that proved Ada's guilt with mathematical certainty. Every page documented betrayal. Every note confirmed what he'd suspected.

He could report to Tommy tomorrow, watch Ada be destroyed, prove his loyalty at the cost of friendship.

Or he could find the third option that always existed if you were clever enough. The solution that protected Ada without betraying Tommy. The manipulation sophisticated enough that nobody realized they were being controlled.

That was his specialty, after all. Finding the elegant solution that satisfied everyone while serving his own interests. Treating people like chess pieces while telling himself it was for their own good.

Intelligence without empathy.

Jimmy stared at his notes until the letters blurred. Then he began planning the most complex operation of his career—protecting Ada by deceiving everyone, including her.

Because that was what he did. That was who he'd become.

The devil's advocate, arguing for solutions that destroyed souls while saving lives.

More Chapters