Chapter 21: The Undertaking's Shadow
Tommy's texts became daily occurrences—invitations to lunch, clubs, random hangouts—and Ben accepted because genuine friendship was forming even as he planned to destroy Tommy's father.
The irony wasn't lost on him. Every coffee meeting, every casual conversation, every moment of authentic connection was built on a foundation of deception that would eventually collapse and bury their relationship in its rubble. But Tommy Merlyn was exactly what he'd appeared to be at the charity gala: a fundamentally decent person trapped by circumstances he couldn't control, reaching out for something real in a world of artificial connections.
"You're the only friend I have who doesn't want anything from me," Tommy said over drinks at his club, oblivious to the way Ben's stomach clenched at the words. "No requests for donations, no networking opportunities, no attempts to get closer to the Merlyn name. Just... friendship. Do you know how rare that is?"
"If only you knew what I really want. If only you knew that your friendship is the perfect cover for infiltrating your father's operations and gathering intelligence that will destroy everything you think you know about your family."
"Everyone wants something," Ben replied carefully. "Maybe I just want different things than most people."
"Like what?"
Ben considered the question while studying Tommy's face—open, trusting, genuinely interested in understanding the person across the table rather than calculating what he might gain from the relationship.
"A city where people don't have to be afraid. Where the powerful can't prey on the powerless just because they have money and connections." Ben took a sip of his drink, tasting bitterness that had nothing to do with the alcohol. "Where sons aren't defined by their fathers' sins."
Tommy's expression shifted, recognition flickering in his eyes. "You think my father is one of the powerful people who prey on others."
"I think your father is planning to commit mass murder, and I'm using our friendship to gather the intelligence needed to stop him. But I can't tell you that without destroying you in the process."
"I think your father is a complicated man in a complicated position," Ben said instead. "And I think you have the opportunity to be better than the worst parts of his legacy."
"What if I don't know how? What if the only examples I've had are cold, calculating people who care more about legacy than humanity?"
Ben's heart broke a little at the genuine vulnerability in Tommy's voice. This was the conversation Malcolm should have had with his son years ago—guidance about becoming a man worth respecting, support for developing moral courage, reassurance that choices mattered more than bloodlines.
"Tommy's worst fears about his father are understatements. Malcolm isn't just cold and calculating—he's planning genocide disguised as urban renewal. But I can't warn Tommy without triggering the Spoiler Curse, and I can't save their relationship without sacrificing the intelligence I need to save the city."
"Your father's choices aren't your destiny," Ben said, offering what comfort he could. "You get to decide who you are, what you stand for, how you treat people who can't do anything for you. Blood doesn't determine character—actions do."
Tommy nodded slowly, some of the tension leaving his shoulders. "Thank you. I needed to hear that."
The gratitude in his voice made Ben's deception feel like a physical weight pressing down on his chest. Tommy was finding genuine support in their friendship while Ben was systematically betraying that trust for what he hoped was the greater good.
"Can I ask you something?" Tommy continued. "Do you think it's possible to love someone and still acknowledge that they've done terrible things?"
He knows. Maybe not the specifics, but he knows something's fundamentally wrong with his father.
"Love and accountability aren't mutually exclusive," Ben said carefully. "You can care about someone while refusing to enable their worst impulses. Sometimes the most loving thing you can do is say no to someone who's lost their way."
Tommy stared into his glass, processing implications that Ben could only guess at. The conversation drifted to safer topics after that—sports, movies, Tommy's attempts to find meaningful work that wasn't connected to Merlyn Global—but the underlying tension remained.
An hour later, Ben found himself in the elevator of Merlyn Global's downtown tower, using Tommy's guest access to visit the restrooms on the fifteenth floor while his enhanced awareness catalogued security patterns and guard rotations. His Prescience activated automatically, blue afterimages showing patrol routes and surveillance blind spots that he memorized for future reference.
The data-scraping device Felicity had designed looked like a standard USB drive, small enough to palm while pretending to check email on one of the public terminals in the building's lobby. Ben inserted it with casual movements, watching it install monitoring software that would track financial transactions and communication patterns throughout Merlyn Global's network.
His powers screamed warnings as he approached the executive floors. Malcolm's presence somewhere above them radiated future violence so intensely that Ben nearly vomited from sensory overload. The Dark Archer was up there, planning atrocities that would reshape Starling City through calculated destruction, and every instinct Ben possessed was telling him to run before Malcolm detected his presence.
Instead, Ben used his Negation ability to erase his digital footprints as he moved through the building. Security cameras glitched occasionally where he walked, their recordings developing convenient gaps that would be attributed to technical errors. His powers working in tandem created ghost-like infiltration capabilities that he was only beginning to understand.
"I'm walking through the headquarters of the man planning to murder thousands of people, gathering intelligence to stop him, while maintaining a friendship with his son who has no idea what kind of monster his father really is. The moral complexity is staggering, but the alternative is letting Malcolm's plan succeed."
Ben extracted himself from the building without incident, the data scraper already transmitting information to Felicity's secure servers. The intelligence would be invaluable for understanding the Undertaking's timeline and scope, but it came at the cost of deepening his deception of the one person in this world who trusted him without reservation.
POV: Tommy
That evening, Tommy sat in his apartment reviewing a conversation that had left him feeling both supported and unsettled. Ben's insights about legacy and personal choice had resonated in ways that suggested understanding born from experience rather than theory.
"He talks about complicated fathers like someone who's wrestled with similar issues. Maybe that's why we connected so quickly—shared experience with disappointing paternal figures. But there's something else, something in his eyes when he talks about powerful people preying on others. Like he's seen the consequences firsthand."
Tommy pulled out his phone and scrolled through his contacts until he found Oliver Queen's number. The two had been friends since childhood, though their relationship had become strained since Oliver's return from the island. Maybe Oliver could offer perspective on the gym teacher who'd somehow become the most genuine friendship in Tommy's life.
"Oliver? It's Tommy. Do you have a minute to talk about someone? I think you two might get along."
Oliver's voice carried the weight of someone perpetually exhausted by responsibilities no one else could understand. "Who are we talking about?"
"Ben Hale. He teaches self-defense in the Glades, but he's also... I don't know how to describe it. Thoughtful. Honest. The kind of person who sees you as human instead of just a name or a bank account."
The pause on the other end stretched longer than Tommy expected. When Oliver finally spoke, his tone carried recognition that Tommy couldn't interpret.
"Ben Hale. Yes, I'm familiar with him."
"Really? How?"
"He's... made an impression around the city. The gym incident with the League operative. The charity auction where he displayed metahuman abilities."
"Oliver knows Ben personally. But why does he sound wary instead of impressed? Ben saved lives, protected innocent people. That should align with whatever mission Oliver's been pursuing since he returned."
"He's a good person, Oliver. One of the few genuine people I've met who doesn't want anything from the Merlyn name."
"I'm sure he is. Just... be careful, Tommy. People aren't always what they appear to be, and men with Ben's capabilities usually have complex motivations."
The warning felt strange coming from Oliver, who'd been hiding his own secrets since returning from the island. Tommy ended the call more confused than enlightened, processing a conversation that had raised more questions than answers.
"Why is Oliver suspicious of Ben? What does he know that I don't? And why do I get the feeling that there are entire conversations happening around me that I'm not privy to?"
Tommy made a decision as he prepared for bed. Ben had been the first person to offer genuine friendship without ulterior motives. Whatever secrets surrounded him, whatever had made Oliver wary, Tommy was going to trust his own judgment about character over other people's paranoia.
"Ben sees me as Tommy Merlyn the person, not Tommy Merlyn the heir. That's worth protecting, whatever complications might arise from the association. He's the brother I always wished I had—someone who believes I can be better than my father's example."
What Tommy couldn't know was that his faith was about to be tested by revelations that would reshape everything he thought he understood about family, friendship, and the price of loving people who carried secrets too dangerous to share.
Ben walked home through the Glades with Felicity's data scraper transmitting terabytes of information from Merlyn Global's servers, intelligence that would be crucial for understanding and disrupting the Undertaking. But the tactical victory felt hollow against the weight of Tommy's trust and the knowledge that their friendship was built on lies that would eventually destroy it.
"I'm living two lives that will inevitably collide. Ben Hale the friend, who listens to Tommy's fears and offers support without judgment. And Ben Hale the infiltrator, who uses that friendship to gather intelligence against Tommy's father. When the Undertaking comes to light and Tommy learns I knew all along, which version of me will he remember? The friend who helped him find his moral courage, or the spy who betrayed his trust for the greater good?"
Ben's coded journal gained new entries that night—financial data patterns, security protocols, and the growing certainty that Malcolm's timeline was accelerating beyond what the show had depicted. But alongside the tactical intelligence, he recorded something more personal: the weight of genuine friendship and the terrible cost of maintaining it through necessary deception.
Outside his window, Starling City hummed with late-night energy, unaware that its salvation was being planned by people who cared about each other enough to lie, and who loved each other enough to risk everything—including their relationships—to keep each other safe.
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