American History Hotline

Episode: Hail to the Cheapskate: How Presidents Made (and Spent) Their Money

Host: Bob Crawford
Guest: Megan Gorman, author of All the President’s Money: How the Men who Governed America Governed Their Money
Date: October 15, 2025

Episode Overview

This episode dives into the surprisingly complex and often messy personal financial histories of America’s presidents—the men whose faces grace U.S. currency but who sometimes struggled to manage their own money. Historian and author Megan Gorman joins host Bob Crawford to answer a listener’s question about Thomas Jefferson dying broke, and from there, the conversation explores presidents who excelled at personal finance and those who spectacularly failed. The discussion highlights personal quirks, family dynamics, and broader economic forces that shaped the fortunes (or misfortunes) of leaders like Jefferson, Washington, Lincoln, FDR, Hoover, and more—right up through modern presidents.

Key Discussion Points & Insights

1. Presidential Winners and Losers at Money Management

• George Washington: Financial Standout

  • "President number one, George Washington—phenomenal with money… same asset base mix [as Jefferson], and yet Washington's phenomenal. Jefferson's quite a failure." (Megan Gorman, 04:32)
  • Washington was hands-on, only accepted real cash (not certificates); actively managed assets even while president.

• Warren G. Harding: Surprisingly Savvy

  • Despite being ranked low as a president, Harding was well-organized financially thanks to prudent management (with help from his wife Florence) of the Marion Star newspaper.
  • Harding’s community-mindedness included ESOPs for employees and investing locally.
  • "Sometimes the traits that make you good at something make you bad at something else…" (Megan Gorman, 06:51)
  • At his death, estate plans were prepared; wife finalized newspaper sale.

2. Thomas Jefferson and the Founders’ Money Problems

• Jefferson’s Lifestyle and Debt

  • Heir to land and enslaved people, Jefferson overspent and mismanaged assets, was generous to a fault, and took on others’ debts (notably his father-in-law’s).
  • Lived beyond his means on luxury goods after returning from France.
  • Failed to appoint a proper steward for his finances.
  • "When he gets to the end of his life, Monticello is falling apart... He ends up doing a lottery... And he dies in debt." (Megan Gorman, 10:04)
  • The real tragedy: Monticello and enslaved families are auctioned off, splitting up generations.

• Jefferson, Madison, Monroe: A Trio of Bad Finance Managers

  • "…as brilliant as the three of them were, they were all horrible with money." (Megan Gorman, 11:46)

3. The Madison-Biden Parallels

• Madison’s overindulgence of stepson, stemming from family trauma, led to financial struggles—mirrored in Joe Biden’s finances post-personal tragedies:
  • "I have a lot of empathy for both Madison and Biden… just by how they handle them with the money, it just never works out." (Megan Gorman, 13:32)

4. Researching Presidents’ Personal Finances

• Easier to access older presidents’ records (e.g., Madison, Truman) than modern ones due to classification and privacy.
• Anecdote: Truman’s wealth revealed only after his daughter’s death and lifting of a classified file.
  • "You don't think—wait, what happened to poor Harry Truman?" (Megan Gorman, 15:41)

5. Abraham Lincoln: From ‘Hot Mess’ to Financially Sound

• Born poor, made early business mistakes, carried personal debt ("my national debt").
• Became financially responsible, investing salary in Treasury bonds during presidency.
  • "He takes every bit of his $25,000 salary and he's saving it in treasury notes and treasury bonds." (Megan Gorman, 19:12)
• Wife Mary Todd Lincoln’s extravagant spending contrasted his thrift.
• Shocking: Lincoln dies without an estate plan, assets divided by the Chief Justice’s oversight.
  • "He really did make the American dream when it came to finance." (Megan Gorman, 21:12)

6. Mary Todd Lincoln and Mamie Eisenhower: Women and Wealth

• Mary came from money but struggled with trauma and drama, contributing to the Lincolns’ mismatched money values.
• In contrast, Mamie Eisenhower (and Ike) shared practical values despite different upbringings.
  • "[Mamie] used to say, Ike is so tight with a buck that when he squeezes a dollar, the eagle screams." (Megan Gorman, 23:52)

7. Franklin Delano Roosevelt: “Terrible with Money, Gold Star for Charity”

• Born into trust fund wealth, disconnected from day-to-day finances.
• His polio led to the purchase (and then charitable transfer) of Warm Springs, and the creation of the March of Dimes campaign.
  • FDR and his business partner invented nonprofit life insurance policies for the survival of Warm Springs.
  • "2.7 million Americans send in dimes. It’s GoFundMe." (Megan Gorman, 35:18)
• Shows FDR’s skill at turning personal misfortune into national philanthropic movements.

8. Why Write About Presidential Finances?

• Gorman discusses her small-town roots, Goldman Sachs career, and fascination with the untold, everyday money struggles of the powerful.
  • "All of us talk about money all the time… you gotta look, dig for the little nuggets like FDR and his lobsters or Richard Nixon and his orange juice company." (Megan Gorman, 37:26)

9. Herbert Hoover: Orphan to Altruist Millionaire

• Early orphan, learned budgeting from his Quaker upbringing, made fortune in global mining.
  • "He's running budgets as a small boy." (Megan Gorman, 39:09)
• Used mining expertise and profits for massive humanitarian efforts in both World Wars.

10. Modern Presidents: Making, Spending, and Branding Money

• The “Jerry Ford Rule” (Post-Presidential Money):

  • Before Ford, ex-presidents wrote books or resumed law practice.
  • Ford developed a model of joint book deals, speeches, corporate boards—setting the stage for Clinton and Obama.
    • Obama’s fortune comes mainly from a best-selling reissued book: "He makes $10 million off the book. Phenomenal." (Megan Gorman, 42:41)

• Joe Biden’s Challenge:

  • His post-presidential earning potential limited due to shifting media markets and brand issues.

• Donald Trump: Profiting While President

  • Trump’s wealth is multi-generational and structured for risk-taking; often makes money “around” core businesses (e.g., lawsuits, branding).
    • "He is very good with pushing the envelope with risk." (Megan Gorman, 47:23)
  • Raises bigger questions about whether presidential financial disclosure laws, written before today’s brand- and influencer-centric world, are still fit for purpose.
    • "Post-Trump, we really need to rework the system." (Megan Gorman, 50:52)

11. Could a "Regular American" Still Become President?

• It’s increasingly unlikely.
  • "Unless you're moneyed or you're celebrity, it is very hard to be the Abraham Lincoln who climbs from nothing and makes it." (Megan Gorman, 51:16)
• Early presidents mostly came from wealth; Andrew Jackson was truly self-made but even he became rich before taking office.
• Still, Megan Gorman is hopeful for a future leader from humble beginnings.

Notable Quotes & Memorable Moments

• On Jefferson’s Estate: "Monticello is falling apart. It's not what we see today… He dies in debt. Monticello goes up for auction, as do the slaves." (Megan Gorman, 10:04-10:54)

• On FDR’s Fundraising: "Eddie Cantor called it the March of Dimes. And literally 2.7 million Americans send in dimes… It’s GoFundMe." (Megan Gorman, 35:16-35:26)

• On Modern Presidential Earnings: "What may have worked for Ford and Bush and Obama and Clinton is not working for Biden because the Biden brand has sort of struggled." (Megan Gorman, 44:39)

• On Trump and Profit: "His money's being made around [his core business]… in Atlantic City…the money…was not really from the casinos. It was from bonuses…he was paid to go away." (Megan Gorman, 48:00-48:20)

• On Future Presidents: "I hope we get back to a point in time where a guy—or a gal—who doesn't have a college education...can make it through." (Megan Gorman, 53:08)

Timestamps for Key Segments

• [04:32] Washington vs. Jefferson on finances
• [05:11] Warren G. Harding’s financial practices
• [08:04] How the Founders made/spent money
• [11:52] Comparing Madison and Biden’s family financial strategies
• [14:41] Research challenges: Madison vs. modern presidents
• [17:49] Abraham Lincoln: debt and late-life wealth
• [19:12] Lincoln as president: saving bonds
• [21:12] Lincoln’s lack of estate plan
• [22:19] Mary Todd Lincoln and Mamie Eisenhower compared
• [30:17] FDR’s upbringing, money habits, and philanthropy
• [35:16] March of Dimes / Charity innovation
• [36:38] Why Gorman wrote about this subject
• [38:09] Herbert Hoover’s financial life and humanitarianism
• [41:39] Modern presidents’ money making: Clinton, Obama, Ford
• [47:23] Trump, branding, and profit while in office
• [51:16] Can a regular American become president?
• [53:19] Final thoughts — can a poor person become president?

Overall Tone & Takeaways

The episode is lively, anecdotal, and rich with historical asides and modern parallels. Megan Gorman blends historical detail and financial analysis with a conversational tone, making complex stories accessible and often surprising. Both host and guest approach politics with empathy and curiosity, reinforcing that ultimately, the men (thus far) who have held the nation’s highest office were as flawed and fascinating in their private struggles with money as any citizen.

For listeners who missed the episode, this summary captures both the content and the captivating storytelling style.