Perhaps the most commonly used and known phrases surrounding all of history, what does this mean in concrete every day terms, or geopolitical analyzations.
The original is from George Santayana; "those who do not remember the past are condemned to repeat it". It's from a big work of his, The Life of Reason: or The Phases of Human Progress, which explored how a great deal of human activity- religious beliefs, social institutions, science , art and culture- have been part of, encouraged, a life of reason. Our conscious decisions carry with them a value judgement that impels us to follow our sense of good, and so reasoning is a natural thing for humans to do.
I read Santayana on metaphysics in college, and because I have forgotten it, I suppose I am now doomed to repeat him. The book itself tries to show humans as naturally reasoning creatures, and humanity as progressive. Memory is key to that. In context:
Progress, far from consisting in change, depends on retentiveness. When change is absolute there remains no being to improve and no direction is set for possible improvement: and when experience is not retained, as among savages, infancy is perpetual. Those who cannot remember the past are condemned to repeat it. In the first stage of life the mind is frivolous and easily distracted; it misses progress by failing in consecutiveness and persistence. This is the condition of children and barbarians, in whom instinct has learned nothing from experience. In a second stage men are docile to events, plastic to new habits and suggestions, yet able to graft them on original instincts, which they thus bring to fuller satisfaction. This is the plane of manhood and true progress.
The altered quote goes much further than Santayana. Instead of just remembering, retaining experience, "Learn from history" sounds very much like the common intuitive assumption that history has durable mechanisms and rules, and that if we can understand the mechanism by which, say, revolutions happen or empires decline, we can avoid them or at least have the smug satisfaction of predicting them. There were plenty of attempts to do that in the 20th c., by ( among others) Oswald Spengler and Arnold Toynbee. But so far, those theories have been as successful as the theories people take with them to casinos, in the expectation of becoming rich.
Sanatayana, George ( 1906) The Life of Reason p.284