The Worst Moments in American History

Jun 24, 2026 - 08:08

An 1823 poster advertising the auction of ten enslaved people in Richmond, Virginia, neers, dated July 23, 1823

1619 (PREDATES 1776)

Establishment of slavery and Dred Scott v. Sandford (1857)
Some respondents focused on the original sin of the slave trade, others on the infamous Supreme Court decision that called enslaved people property, but they were all saying the same thing: Slavery, while not a single “moment,” was our greatest shame.

An illustration depicting the Trail of Tears, showing Native American men, women, and children o the trail

1830–1850

Indian removal/Trail of Tears
The forced removal and ethnic cleansing of some 60,000 Native Americans. Wrote one survivor: “Many days pass, and people die very much.” It was led by Andrew Jackson. Whose portrait now hangs in Donald Trump’s Oval Office.

illustration of Confederate soldiers firing cannons at Fort Sumter marking the start of the Civil War,

1861

Firing on Fort Sumter/the Civil War
Lincoln had just been elected. South Carolina had just seceded and insisted that the U.S. Army abandon its military installations in the state. It refused. South Carolina’s militia attacked. The Civil War was underway. color illustration of John Wilkes Booth shooting President Abraham Lincoln

1865

Lincoln’s assassination
John Wilkes Booth vowed that a speech he heard Lincoln give on April 11 would be his last. And so it was. An act that felled our greatest president—and gave us one of the worst. Black and white photograph of four masked Ku Klux Klan members in white robes and pointed hoods

1877

Compromise of 1877 ending Reconstruction
The political deal that ushered in the era of the Ku Klux Klan and Jim Crow laws. Oh, and finagled the presidency away from the guy who got more votes. Sound familiar? A black and white photograph the aftermath of the 1921 Tulsa Race Massacre

1921

Tulsa Massacre
Two days of mob violence that destroyed 35 square blocks and left 10,000 Black people homeless. And it took seven decades for the state to form a commission to acknowledge and study it. A colorized photograph of a boat exploding during the Japanese attack on Pearl Harbor

1941

Pearl Harbor
Japan attacked a naval base in Hawaii and ended America’s neutrality in World War II. The “date which will live in infamy,” in FDR’s famous phrase. His first draft? “A date which will live in world history.” Most important speech edit in history? A Japanese American men, women, and children behind a barbed wire fence at a WWII era internment camp

1942

Japanese American internment in World War II
Without question, FDR’s low point—120,000 Japanese Americans (80,000 of them citizens) sent to 10 camps. The Supreme Court defended this in 1944’s Korematsu v. United States, which has gone down in history as one of its worst decisions. The massive mushroom cloud rising over Nagasaki, Japan, following the detonation of the atomic bomb

1945

Dropping atomic weapons on Japan
Harry Truman said he never lost a night’s sleep over the decision to drop the bombs that ultimately killed nearly 200,000 people. It did shorten the war—but it launched a dark and paranoid era in human history. Smoke from the Twin Towers over the Manhattan skyline following the terrorist attacks of September 11, 2001

2001

9/11
Three items on this list are not things the United States did, but things done to the United States. This one was awful: Four planes attacked the country, killing nearly 3,000 people and injuring thousands more. It was made even worse by our government’s overreaction.

2021

January 6
It’s still hard to believe that a sitting president led an insurrection against the United States of America and was at best indifferent to the idea of the mob killing his own vice president. Donald Trump stands at a podium in a navy suit and red tie

2024

Reelection of Donald Trump
Future historians will ask how the hell the American people decided to do this. Let’s just hope those historians are still living in a democracy.