If you ever find yourself debating the legacies of America’s “Roosevelts”—Theodore (“Teddy”) or Franklin Delano (“FDR”)—you’ll quickly discover each presidency is a minefield of heated opinions. You might think you know the broad strokes: trust-busting Teddy, New Deal FDR, the Panama Canal, WWII. But living with their controversies feels totally different when you dig through firsthand accounts and real policy fallout. This article unwraps several major criticisms—some legit, some wildly overblown—that dogged each Roosevelt during their time in office, pulling examples from archival news, legal texts, and even modern forums where historians love to argue. Plus, I’ll share a story where my own research seriously derailed thanks to conflicting sources… and why being skeptical is half the fun.
Right out of the gate, Teddy comes off as a reformer’s reformer. But the halo effect wears off quick when you look at the grievances his era left behind. Here’s what actually happened on the ground, plus a short detour for when my own archival dive got seriously sidetracked by one spicy Congressional hearing transcript.
TR’s most famous for smashing monopolies—his Justice Department filed suits against more than 40 big companies, including Standard Oil and Northern Securities. A lot of small business owners cheered. But, real-talk, plenty of investors (and even jurists) thought he destabilized the stock market and threatened economic growth.
Personal moment: Once, digging through Library of Congress archives, I found this 1907 Northern Securities decision (from the Supreme Court!), which literally says monopolies “restrain trade.” But check the May 19, 1903, New York Times—investors freaked out, calling TR’s antitrust crusade reckless. Some even say it triggered minor panics. There’s always a tradeoff.
Random blunder: First time I read Roosevelt’s own autobiography, I totally missed his dig at “predatory wealth”… only noticed it after a grad school friend pointed out I’d skipped a section. Oops. Details matter!
Teddy’s foreign policy was pure swagger. He negotiated peace for Russia and Japan (and nabbed a Nobel Prize for it), but experts from the Council on Foreign Relations often cite how his “speak softly and carry a big stick” approach also aggravated both Latin American and Asian governments. Classic example: literally orchestrating Panama’s “independence” from Colombia so the US could scoop up the Canal rights (see U.S. State Department docs).
When I tried to untangle legislative details, I found that the Spooner Act of 1902 (31 Stat. 733) actually gave Roosevelt executive power to negotiate for the Canal Zone. But, when he bypassed Congress and acted before a treaty was ratified, plenty on Capitol Hill called him “imperialist.” Can’t say they were wrong.
Teddy invited Booker T. Washington to dinner at the White House—the first time an African American had done so. Sounds like progress, right? But then the Brownsville Affair (1906) happened: Roosevelt dishonorably discharged an entire regiment of Black soldiers accused (without proof!) of shooting in Texas. Later investigations cleared them, but the damage was done.
From a current perspective, data shows that TR’s purportedly “progressive” social stances came packaged with the prejudices of his time. Author Clay Risen wrote a solid breakdown of this contradiction.
Suppose you’re a Colombian diplomat in 1903 seeing Roosevelt’s U.S. recognize Panama within hours of its breakaway. Your response? “That’s not negotiation—that’s a land grab!” International law even today debates U.S. actions under the Hague Conventions. Specialist Dr. Peter Klaren from George Washington University on C-SPAN describes it as “21st-century realpolitik using 19th-century rationale.” This divide persists in scholarly reviews, such as those by the OECD on sovereignty disputes (OECD, 2017).
Let’s fast-forward 30 years. FDR came into office with America at rock bottom—think soup kitchens, dust bowl, banks collapsing fast. The sweeping policies and executive orders that made him popular also created backlash that still divides experts.
FDR literally remade government’s role in the economy: Social Security, Works Progress Administration, SEC. Some critics saw it as saving capitalism from itself; others, most notably the Supreme Court, found parts like the National Recovery Administration unconstitutional (Schechter Poultry Corp. v. United States [1935]). Up to 1937, courts often blocked key ideas—prompting the infamous “court packing” plan where FDR tried (and failed) to add more sympathetic justices. Can you imagine that squabble today? Twitter would explode.
Expert take: According to Brookings Institution, this episode “damaged FDR politically and emboldened opponents on all sides.”
Tidbit from my own research: I tried to map all New Deal agencies for a comparative law class—honestly got lost halfway. There were at least 100 by 1939!
Despite progress elsewhere, FDR’s decision to sign Executive Order 9066, leading to the internment of over 110,000 Japanese Americans during WWII, remains shocking and deeply criticized even today. The National Archives hosts original materials—firsthand accounts are absolutely harrowing. Decades later, both Congress and Presidents issued formal apologies and reparations (see 1988 Civil Liberties Act).
On other civil rights issues, FDR’s record is… mixed at best. While he appointed the first Black federal judge (William Hastie), his primary concern was coalition-building, which led to slow progress on anti-lynching laws (often blocked by Southern Democrats). The NAACP and American Civil Liberties Union were vocal in their criticisms—you can still find their reports in the NAACP archives.
Most presidents get their wartime decisions criticized, but with FDR it reached new heights. He expanded executive authority in ways that alarmed civil libertarians, including wiretaps and media censorship as per wartime orders detailed in U.S. State Department histories. Congress authorized broad latitude with statutes like the First and Second War Powers Acts.
Yet, he faced sharp criticism post-Pearl Harbor for gathering intelligence on Americans and for not doing more, sooner, to rescue European Jews from the Nazis—a contentious topic even among his staff, as per the U.S. Holocaust Memorial Museum.
Just for fun (and because trade rules often mirror presidential power struggles), here’s a quick snapshot of how trade verification standards differ today, using real references.
| Name | Legal Basis | Enforcement Agency | Typical Dispute Approach |
|---|---|---|---|
| USA: "Customs-Trade Partnership Against Terrorism" (C-TPAT) | 19 U.S. Code § 1411 | U.S. Customs and Border Protection (CBP) | Voluntary, company certification, random audits |
| EU: "Authorised Economic Operator" (AEO) | Regulation (EU) No 952/2013 | National Customs with EU oversight | Centralized electronic certification, mutual recognition |
| China: "Advanced Certified Enterprise" (ACE) | General Administration of Customs Order 243 | GACC (General Administration of Customs China) | On-site checks, documented supply chains |
| OECD Model: "WTO Trusted Trader" | WTO TFA Article 7.7 | National Agencies/OECD review | Country-by-country negotiation, periodic review |
All these agencies aim to “verify trade,” but the mechanics differ. If TR were around, he’d probably demand unilateral U.S. standards, “the Roosevelt way.” FDR? Likely to push for multilateral rules, but with strong U.S. controls behind the scenes. The friction between “big stick” and “New Deal” even shows up in today’s customs wars—just check any WTO dispute panel ruling!
“Look, trade verification isn’t just bean-counting,” jokes retired CBP official Janet L. during a panel I attended last year, “it reflects how much trust you have in your partners. Remember, every Roosevelt tried to set the rules they liked best—sometimes it worked, sometimes Congress or the courts reined them in. That’s still true in global trade. If you don’t handle certification disputes wisely, everybody loses.”
Living with the consequences of presidential ambition takes more work than reading a textbook. When you push the system—like both Roosevelts did—expect enormous blowback from rivals, reformers, and sometimes your own cabinet. My own dive into their controversies left me surprised at how recognizable the arguments feel: executive overreach, minority rights, foreign entanglements, and fights over what “the American way” ought to be.
I’ll be honest—if you want a tidy narrative, you won’t get it. The day I tried to draw up a chart of all FDR’s New Deal agencies for a side project, I ended up late for dinner and still didn’t have a clear answer. Turns out, neither did Congress in 1935. History is gloriously messy that way.
Both Theodore and Franklin Roosevelt faced firestorms of criticism in their days, much of it about executive power, overreach, and the cost of change. On everything from race to foreign policy, their legacies are as fractured as the U.S. itself. Yet, digging into their critics’ arguments gives a richer picture than “heroes or villains.” My suggestion? Check the links above, read the original Supreme Court decisions, peek at those old headlines and letters. If you want the real story (not just the myth), you’ve got to chase the mess, not just the highlight reel.
Want to keep exploring? Start by comparing how current leaders handle some of the same issues—trade negotiations, executive orders, civil liberties. Maybe try mapping agencies too… just don’t do it at the expense of your dinner plans.
For further reading and to fact-check anything here, check out:
- U.S. State Department: Office of the Historian
- Federal Supreme Court database
- OECD: Trade Certification Guidance
- CBP C-TPAT
Any errors or misreadings are mine—take the journey and argue back! Roosevelt’s story is still being written.