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The Erie Railroad [1], founded 1832, bankrupt in 1859, 1878, 1893, 1938, and 1976, now largely in disrepair. Woolworths [2], founded 1878, the first department store in the country, once owned the tallest building in the world. Started losing market share to Sears & catalog retailers in the 1930s, defunct in 1997. Sears was itself eclipsed by WalMart, which is on the verge of being eclipsed by Amazon. International Mercantile Marine [3], owners of the Titanic, once monopolized shipping so thoroughly that the British government paid to keep Cunard (its only competitor) alive. Bankrupt in 1916, sold White Star Lines in 1926 to a company that collapsed in 1934, lost 2/3 of its fleet in the 5 years between 1930-1935, acquired in 1931, divested all passenger vessels by 1968, bankrupt in 1986. TWA [4], founded via merger in 1930, almost went bankrupt in 1931, dissolved by act of Congress in 1934 but the brand was maintained by one of the daughter companies, purchased by Hughes in 1938, forced (by the government) to be sold in 1966, purchased by Icahn in 1985, bankrupt 1992, bankrupt 1995, final bankruptcy 2001. There's a pretty massive survivorship bias when looking only at companies you've heard of, and even if they've survived in name for a century, it's not unusual for them to have periodic bankruptcies every 10-20 years that wipe out the shareholders. [1] https://en.wikipedia.org/wiki/Erie_Railroad [2] https://en.wikipedia.org/wiki/F._W._Woolworth_Company [3] https://en.wikipedia.org/wiki/International_Mercantile_Marin.... [4] https://en.wikipedia.org/wiki/Trans_World_Airlines |
Even older companies I forgot to include: Citigroup, the NYSE.