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World War II for most of the Allies. They won, obviously, but even countries that got off 'lightly' tended to suffer a causalty rate in the range of tens of thousands, the majority with over 100,000 dead, the major ones with over one million dead for a grand total of approx 50 million dead (no one knows for sure). Oh, and even as World War II ends and everyone is celebrating, the Iron Curtain descends and the world is plunged into an additional 40 years of the Cold War.
In the Eastern Bloc this was even more notable as they lost more people as a percentage of their populations than anywhere else. Poland and the western portion of the Soviet Union (Ukraine, Belarus, Lithuania) lost on average about 15% of their total populations. Hungary and Czechoslovakia didn't fare all that much better. And then they were under the thumb of Stalin. The gulag was busy in the immediate post-war period.
The Cold War and Hole in Flag revolutions. The Soviet Union broke up, communism fell, and a tense nuclear situation was averted, but it left Slavic people with widespread poverty throughout the 90s and privatization left much of its successor state's wealth in the hands of oligarchs. Not to mention, ethnic tensions bubbled up to the surface and left us with 10 years of Yugoslav wars.
Some former Soviet countries, like Ukraine, have yet to recover their GDP as it was upon their independence. This is over 20 years after the fact. Moldova is the poorest country in Europe and its per capita GDP of about 1500 US dollars makes neighboring Romania seem wealthy.
Also, while the Cold War did put an end to one of the most oppressive and violent empires in history, it also left many third world nations across Asia, Latin America, and Africa scarred from the proxy wars the Soviet Union and the United States fought there.
The American Civil War preserved the Union and ended slavery, at the cost of over 600,000 lives and the destruction of large parts of the South. Abraham Lincoln became in effect one of the last casualties of the war, and the aftermath saw the freed slaves and their descendants facing Jim Crow for more than a century after, ongoing sectional conflict and bitterness, and the expansion of the United States into the West and the fulfillment of "Manifest Destiny," which led to the eventual cultural destruction of most of the Native American nations.
All of you. Even a long happy life full of friends and love ends with death and (temporary or permanent, depending on your beliefs) separation from friends and family.
Thanks to the Butterfly Effect, your very existence will alter trillions of organisms long after you die. And, of course depending on your belief system, even death may not be the end. And we'll leave it at that.
Once war breaks out, the best possible ending is bittersweet... in a large scale. If it's imperialism and you're the empire, jolly good for you.
After any major disaster. ANY. New Orleans after Katrina, New York after September 11, 2001. Hiroshima and Nagasaki after the Bomb, the Gulf Coast after the Deep Horizons oil spill, etc. Yes, you may stop/survive the damage, but after large-scale disasters like that nothing goes back to the way it was.
The K-Pg. On the one hand, it cleared the way for mammals, and eventually ourselves. On the other, it wiped out the non-avian dinosaurs, not to mention pterosaurs, mosasaurs, ammonites, and many others.
Earlier, the Permian extinction. It opened the way for all lifeforms that survived, but eliminated nearly all synapsids, bizarre amphibians and many, many other living beings that would never have parallel forever.
As for the universe, history will repeat (but not before the Dark Era) since God will be creating another universe. There is no "until when" anyway.
Losing your innocence could count as a bittersweet ending to your childhood.
Key word: could. It really depends on 1) what you count as "innocence" and 2) what your childhood was like in the first place.
In the context of Canadian Politics, NDP supporters, BQ critics, and perhaps even those who are neither might consider the more recent Canadian election bittersweet. Jack Layton's campaigning won over an increasing number of NDP votes in Canada, taking votes from many other parties, especially the BQ, and Jack Layton became official opposition leader... but died soon afterwards. Pushing the BQ downwards and the NDP to second-place was a huge change to Canadian politics, but the leading force for it only got to see a couple months' worth of the results.
The Battle of Trafalgar was this for Great Britain. Britain was safe from invasion, Bonaparte's Europe could be blockaded by the world's largest navy. But Horatio Nelson was dead, and a storm meant that barely anyone got paid prize money.
Pick a crash, an accident, a major disaster. Any documentary covering the incident will most likely note the safety changes made as a result, usually in the end. Still, it leads to the Fridge Horror that it seems that nobody would notice design failures unless a crash happened - more so if the changes were major and the fatalities were abundant.