Whenever you're sitting across from some important person, always

Host: The rain had just stopped, leaving a silver haze hanging over the city. Steam rose from the pavement like ghosts escaping the ground. The office tower stood silent, its windows reflecting the fading sunset. Inside, the lights hummed low, casting long shadows on the mahogany table where Jack and Jeeny sat across from each other.

Jack’s tie was loosened, his sleeves rolled, his expression sharp with the kind of fatigue that only money and power could buy. Jeeny’s hands rested gently on a cup of tea, her eyes steady, calm — like a quiet lake before a storm.

The air between them felt dense, charged — as if the room itself were listening.

Jeeny: “You know, Jack, I read something today. Joseph P. Kennedy once said, ‘Whenever you're sitting across from some important person, always picture him in a suit of long red underwear.’”

Jack: (a dry laugh) “Ah, yes. A reminder that even the so-called giants are just men underneath the fabric. A good business trick. Keeps you from shaking when you’re across the table from a shark.”

Host: A draft slipped through the window, fluttering the papers on the desk. Outside, the city lights blinked like a constellation trapped in glass.

Jeeny: “You call it a trick. I call it a form of humility. To remember that even the mighty are human — that’s not mockery, Jack, that’s grounding.”

Jack: “Humility? No, Jeeny. It’s strategy. It’s about disarming the illusion of power. When you see through the costume, you see the person, and once you see the person, you can negotiate, influence, or even defeat them. Business isn’t a prayer, it’s a game of nerves.”

Jeeny: “But isn’t that cynical? Reducing people to costumes and psychology? Maybe the illusion isn’t what needs to be broken — maybe it’s the fear that does. Respect doesn’t mean submission, Jack.”

Host: Jack’s jaw tightened. The city glow lit his grey eyes, making them seem almost metallic.

Jack: “You’ve never sat in a room where a man can erase your career with a single word, have you? I have. In those rooms, it’s not about respect — it’s about control. Kennedy understood that. He wasn’t mocking them; he was equalizing the field. If you can’t make the giant smaller in your mind, you’ll always stay under his boot.”

Jeeny: “So, you fight fear with contempt?”

Jack: “No. I fight it with clarity.”

Host: The clock on the wall ticked — slow, heavy, like a heartbeat between them.

Jeeny: “You think seeing someone’s underwear gives you clarity?” (a small laugh escapes her) “Maybe it gives you a false one. We all wear armor — not because we want to deceive, but because we’re fragile. The suit, the titles, the rituals — they’re just ways of protecting ourselves from being seen too much.”

Jack: “And that’s exactly why it’s useful. Once you recognize that fragility, you can predict behavior. You can anticipate their moves. Roosevelt, Churchill, Kennedy — they all played that game. Not because they were heartless, but because they understood that leadership is a theater. You don’t win by believing the stage is real.”

Host: Jeeny leaned back, her eyes searching his face. A silence settled — the kind that makes truth heavier than words.

Jeeny: “But you’re missing the point, Jack. Kennedy’s advice wasn’t about humiliation. It was about liberation — from awe, from fear, from idolatry. You don’t have to strip someone to feel equal. You have to see them — truly see them — in their humanity.”

Jack: “And how do you ‘see’ someone when the whole system is built to mask them? When power walks in with a smile that hides calculation? When the handshake you’re given is already a deal made elsewhere?”

Jeeny: “You look beyond it. You see the human first. Gandhi faced the British Empire without a gun, Jack — and won. Because he saw through not just the uniform, but through the idea that it made the man invincible. That’s what Kennedy meant, too — he wasn’t saying laugh at them, but don’t worship them.”

Host: Jack’s fingers drummed the table. The sound echoed like a soft thunder.

Jack: “Maybe. But Gandhi’s world ran on belief. Today’s runs on leverage. You walk into a boardroom, and belief doesn’t pay the bills — results do.”

Jeeny: “Then maybe that’s the problem, Jack. We’ve turned every interaction into a transaction. Kennedy’s advice, stripped of its humor, was still about balance — not losing your self in the shadow of another. You take it as a weapon; I take it as a mirror.”

Host: The light from the desk lamp caught in Jeeny’s eyes, making them gleam like amber glass.

Jack: “A mirror, huh? Then why does it feel like you’re always looking for something holy in a room full of wolves?”

Jeeny: “Because even wolves have souls.”

Host: Jack’s laugh was sharp, but not cruel — the kind that hides a deeper ache.

Jack: “You really think that?”

Jeeny: “I have to. Otherwise, what’s the point of any of it? If all you see is weakness to exploit, you become the thing you fear. Kennedy was a pragmatist, yes — but beneath that, there was humor, humanity. The red underwear wasn’t a sneer; it was a reminder to never kneel before pretension.”

Jack: “So it’s not about power, it’s about perspective?”

Jeeny: “Exactly.”

Host: The rain began again, tapping softly against the glass. Jack stood, his silhouette framed against the window, watching the city blur into streaks of light.

Jack: “You know, I once had a meeting with a senator. Big deal. Everyone said I’d be crushed. I spent the night before memorizing numbers, facts, defenses. But when I walked in, he was eating a donut, his tie stained with coffee. He looked… ordinary. And for a moment, I felt exactly what Kennedy meant. The armor cracked. And I wasn’t afraid.”

Jeeny: “And what happened?”

Jack: “We made a deal. A good one. But I didn’t feel like I’d beaten him. I felt… free. Like I’d finally seen behind the curtain.”

Jeeny: “That’s it, Jack. That’s the truth. Not mockery, not control — just the understanding that no one, no matter how powerful, is more than human.”

Host: The air softened. The tension dissolved into a quiet mutualness. Jack turned, his expression lighter now, almost tender.

Jack: “So maybe you’re right. Maybe Kennedy wasn’t laughing at power — maybe he was laughing at fear itself.”

Jeeny: “And maybe that’s the kind of humor the world needs more of.”

Host: They both smiled, faintly, the way people do when they’ve just seen something simple and profound at once. The office lights flickered; outside, the city pulsed like a living organism — restless, relentless, human.

A gust of wind pressed against the window, and for a fleeting moment, the reflection of Jack and Jeeny blurred together — two figures, once opposed, now softened into one shared understanding.

Host: In the end, Kennedy’s joke was more than business wisdom. It was a quiet invitation — to strip the world of its illusions, not out of disdain, but out of recognition. To remember that beneath every title, every suit, every mask, there is a trembling, laughing, very human heart.