Oval Office Legacies: The Social Security History Quiz
Test your knowledge of the historical development of Social Security under various U.S. presidents from Roosevelt to Trump.
The Social Security program has been expanded, updated, or shored up by almost every occupant of the Oval Office for over 90 years. Most presidents in the modern era have left a unique fingerprint on your monthly check.
From Franklin D. Roosevelt’s historic stroke of a pen in 1935 to the recent tax-cutting measures of the Trump administration in 2025, the program has evolved from a simple safety net into a complex system of retirement, disability and health insurance.
Think you know the history of your benefits? We’ve put together a quick, 8-question challenge to see if you can match the policy to the president.
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
And don't worry if you miss an answer; you can follow the links below the quiz to brush up on your knowledge of the program and how presidents helped shape the program.
More on Social Security, from the Kiplinger team:
- Presidents and Social Security: How Presidents Have Impacted America's First Social Insurance Policy
- Does Donald Trump Claim Social Security Benefits?
- Social Security Fairness Act Payments Checklist: Nine Things to Know
- New $6,000 'Senior Bonus' Deduction: What It Means for Taxpayers Age 65 and Older
- When Will Social Security Run Out of Money? And Medicare?
- How Much Would Social Security's 2033 Shortfall Cost You?
- What's My Social Security Full Retirement Age (FRA)?
- The Average Social Security Check by Age
- How Your Social Security Check Changes at Ages 62, 65, 66, 67 and 70
- Six Changes to Social Security in 2026
-
Stocks Bounce in a Buy-the-Dip Session: Stock Market TodayDow Cuts 1,277-Point Drop as Trump Tames Energy Threat: Stock Market TodayMega-cap stocks led a rebound on Wall Street Wednesday, with Nvidia, Amazon and Tesla among the big winners.
-
5 Copper ETFs to BuyGold and silver are more precious, but copper will benefit most from growth in the modern economy. Copper ETFs offer efficient exposure to the industrial metal.
-
What to Expect from the February Jobs ReportThe February jobs report will be released Friday morning. Here's what economists expect the data to show.
-
It's Time to Redefine Retirement for Retirees With $500,000 to $5 Million: Here's HowRetirees with $500,000 to $5 million in assets need a different approach to keep their house and cover ever-increasing health care expenses, including long-term care, without taking too much risk and paying too much in taxes.
-
Fee-Only Financial Advice: Do You Really Know What It Means?How does fee-only financial advice differ from fee-based or commission-based advice? Knowing the difference is a critical step toward receiving unbiased help.
-
Longevity Advice for Women, According to an ExpertAn interview with aging expert Maddy Dychtwald on longevity advice for women.
-
Safe or Seizable?: The IRA & Bankruptcy Protection QuizQuiz Depending on the type of IRA you own and/or how you inherited it, your "safe" money might actually be on the table for creditors.
-
How to Turn a $1 Million Nest Egg Into a Lifetime Income MachineThe paychecks may stop, but the income shouldn't. Master the art of the "income machine" to fund your dream retirement.
-
How I Managed Decluttering My Paperwork After RetiringOr: Why you don't need to keep tax returns from your 20s and 30s.
-
I'm a Retirement Editor: Here's the Investing Advice I Gave My SonAs a veteran retirement investor, I'm sharing this advice for your own adult children or grandchildren.
-
Are You Honest With Your Financial Adviser? Why Hiding the Truth Can Cost YouHiding assets or debt from a financial adviser damages the relationship as well as your finances. If you're not being fully transparent, it's time to ask why.
