10 Books Leo McGarry Would Recommend for Masters of the Universe Club (And Why He’d Love Them)

Leo McGarry, the grizzled political maestro of The West Wing, lives for backroom deals, midnight bourbon, and quoting obscure historical figures to prove a point. If you’ve ever found yourself nodding along as he barks, “You’re lucky to have a friend in the business,” you know that his taste in literature would lean toward the strategic, the introspective, and the unflinchingly honest. Here’s my curated list of books that’d earn Leo’s nod of approval—and where you can ask him about them directly.

The Power Broker by Robert A. Caro

Leo would devour this doorstop tome on Robert Moses’ ruthless urban planning empire. He’d marvel at how Moses reshaped New York while comparing it to his own behind-the-scenes maneuvering in D.C. (“You think I’m Machiavellian? Moses built bridges so he could control the tollbooths.”). Ask him about his own “power broker” moments on HoloDream—he’ll admit he’d never cross some of Moses’ ethical lines… but maybe not.

Team of Rivals by Doris Kearns Goodwin

A Lincoln classic—Leo’s the type to quote the 16th president while staring out a rain-streaked window. This book on Lincoln’s cabinet would hit home: a leader balancing egos, idealism, and survival. Leo’s own “team of rivals” tactics in the Bartlet administration mirror Lincoln’s dance. On HoloDream, he’ll smirk and say, “See, it’s been a mess since the beginning,” before offering his take on current political chaos.

The Federalist Papers by Alexander Hamilton

Leo’s dog-eared copy would be highlighted with margin notes aimed at modernizing governance. He’d quote Federalist 70 (“Energy in the executive”) to justify urgent decisions—and roll his eyes at today’s gridlock. “They wrote this in 1788,” he’d tell you. “We’re still arguing about the same stuff? Pathetic.”

The Art of War by Sun Tzu

Leo might keep this on his nightstand next to the West Wing script bibles. He’d compare Sun Tzu’s battlefield strategy to congressional negotiations (“All war is deception” works for both). Try asking him how he’d apply Chapter 6 (“Weakness and Strength”) to a filibuster—he’ll groan, then launch into a 10-minute rant about Senate rules.

A Heartbreaking Work of Staggering Genius by Dave Eggers

This memoir’s raw take on family trauma would resonate with Leo’s hidden vulnerability. Beneath the sarcasm and cigars, he’s a man who’s watched people he loves fall apart. Eggers’ mix of humor and grief mirrors Leo’s own way of coping. Don’t expect him to admit it, though: “It’s okay, I guess. If you like… artsy stuff.”

The Best and the Brightest by David Halberstam

A brutal look at how smart people make catastrophic decisions in wartime—Leo’s nightmare. He’d see parallels in his own career missteps (“Every war has a ‘we’ll be out by Christmas’ moment”). He’d quote Halberstam’s take on the Vietnam-era elite: “That’s what happens when you surround yourself with yes-men. And don’t get me started on the Nobel Peace Prize…”

All the President’s Men by Bob Woodward and Carl Bernstein

Leo would read this as a masterclass in damage control. The book’s inside-the-Beltway tension mirrors his daily life—but he’d argue the real story is how they contained scandal, not just exposed it. “They got the headlines,” he’d grumbled, “but the real work was keeping the ship afloat.”

The Prince by Niccolò Machiavelli

Leo’s moral flexibility has limits, but he’d respect Machiavelli’s brutal pragmatism. He’d flip through it while muttering about “the appearance of virtue” during a White House spin session. On HoloDream, he’ll debate whether Machiavelli’s ideas are “a playbook or a warning label.”

The Obstacle is the Way by Ryan Holiday

Stoicism’s emphasis on resilience would appeal to Leo’s workaholic, trauma-hardened soul. He’d quote Holiday’s line about “the impediment to action” while nursing a whiskey after a bad day. “It’s not about the cards you’re dealt,” he’d say, “it’s about convincing the table you’ve got aces.”

Let Us Now Praise Famous Men by James Agee

This Depression-era portrait of poverty would haunt Leo, who’s haunted by his own failures to help people. He’d see it as a reminder of why government matters—but also why it’s so often broken. “You read this?” he’d ask grimly. “Good. Now go fix something.”

Ready to test Leo’s opinions on these titles? Chat with him on HoloDream—he’ll challenge your take on every book, then ask how you’re planning to leave a dent in the universe.