Following Ta-Nehisi Coates's strong recommendation, I just finished reading Ryan Lizza's article on Barack Obama's political career during the decade before he became a star on the national stage (with his fantastic Keynote Address at the Democratic National Convention in 2004, and his election to the Senate later in the same year).
Lizza's account is rich with events and anecdotes that keep driving it (almost relentlessly) towards these broad conclusions about the candidate:
Perhaps the greatest misconception about Barack Obama is that he is some sort of anti-establishment revolutionary. Rather, every stage of his political career has been marked by an eagerness to accommodate himself to existing institutions rather than tear them down or replace them. When he was a community organizer, he channelled his work through Chicago’s churches, because they were the main bases of power on the South Side. He was an agnostic when he started, and the work led him to become a practicing Christian. At Harvard, he won the presidency of the Law Review by appealing to the conservatives on the selection panel. In Springfield, rather than challenge the Old Guard Democratic leaders, Obama built a mutually beneficial relationship with them. “You have the power to make a United States senator,” he told Emil Jones in 2003. In his downtime, he played poker with lobbyists and Republican lawmakers. In Washington, he has been a cautious senator and, when he arrived, made a point of not defining himself as an opponent of the Iraq war. Like many politicians, Obama is paradoxical. He is by nature an incrementalist, yet he has laid out an ambitious first-term agenda (energy independence, universal health care, withdrawal from Iraq). He campaigns on reforming a broken political process, yet he has always played politics by the rules as they exist, not as he would like them to exist. He runs as an outsider, but he has succeeded by mastering the inside game. He is ideologically a man of the left, but at times he has been genuinely deferential to core philosophical insights of the right.