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Test your knowledge of the historical development of Social Security under various U.S. presidents from Roosevelt to Trump.
By
Donna LeValley
published
10 February 2026
in Features
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Signup + An account already exists for this email address, please log in. Subscribe to our newsletterThe 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.
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Sign upAnd 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.
We curate the most important retirement news, tips and lifestyle hacks so you don’t have to. Subscribe to our free newsletter, Retirement Tips.
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
Donna LeValleyRetirement WriterDonna joined Kiplinger as a personal finance writer in 2023. She spent more than a decade as the contributing editor of J.K.Lasser's Your Income Tax Guide and edited state specific legal treatises at ALM Media. She has shared her expertise as a guest on Bloomberg, CNN, Fox, NPR, CNBC and many other media outlets around the nation. She is a graduate of Brooklyn Law School and the University at Buffalo.
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