In an article from 2009, Jim Geraghty traces the influence of Saul Alinsky (who died before Obama went to high school) on the President’s early days in office:

Alinsky died in 1972, when Obama was 11 years old. But three of Obama’s mentors from his Chicago days studied at a school Alinsky founded, and they taught their students the philosophy and methods of one of the first “community organizers.” Ryan Lizza wrote a 6,500-word piece on Alinsky’s influence on Obama for The New Republic, noting, “On his campaign website, one can find a photo of Obama in a classroom teaching students Alinskian methods. He stands in front of a blackboard on which he has written ‘Relationships Built on Self Interest,’ an idea illustrated by a diagram of the flow of money from corporations to the mayor.”

In a letter to the Boston Globe, Alinsky’s son wrote that “the Democratic National Convention had all the elements of the perfectly organized event, Saul Alinsky style. . . . Barack Obama’s training in Chicago by the great community organizers is showing its effectiveness. It is an amazingly powerful format, and the method of my late father always works to get the message out and get the supporters on board. When executed meticulously and thoughtfully, it is a powerful strategy for initiating change and making it really happen. Obama learned his lesson well.”

As a tool for understanding the thinking of Obama, Alinsky’s most famous book, Rules for Radicals, is simultaneously edifying and worrisome. Some passages make Machiavelli’s Prince read like a Sesame Street picture book on manners.

He also took advantage of the innumeracy of many people:

When Obama announced a paltry $100 million in budget cuts, and insisted this was part of a budget-trimming process that would add up to “real money,” he clearly understood that the public processes these numbers very differently from the way budget wonks do. Alinsky wrote: “The moment one gets into the area of $25 million and above, let alone a billion, the listener is completely out of touch, no longer really interested, because the figures have gone above his experience and almost are meaningless. Millions of Americans do not know how many million dollars make up a billion.”

That’s the same sense that Mark Steyn captured recently.

Alinsky sneered at those who would accept defeat rather than break their principles: “It’s true I might have trouble getting to sleep because it takes time to tuck those big, angelic, moral wings under the covers.” He assured his students that no one would remember their flip-flops, scoffing, “The judgment of history leans heavily on the outcome of success or failure; it spells the difference between the traitor and the patriotic hero. There can be no such thing as a successful traitor, for if one succeeds he becomes a founding father.” If you win, no one really cares how you did it.

[. . .]

Moderates thought they were electing a moderate; liberals thought they were electing a liberal. Both camps were wrong. Ideology does not have the final say in Obama’s decision-making; an Alinskyite’s core principle is to take any action that expands his power and to avoid any action that risks his power.