Obama and the elder Jackson have much in common: The two black men emerged from Chicago's decayed South Side as champions of poor people. Both have a gift for rhetoric. Both have run to be the nation's first black president.
There are long-standing friendships between some members of their families.
Yet the two are not close. Twenty years older, Jackson, the trailblazer, was never Obama's mentor.
Jackson has always been more flamboyant and confrontational, Obama more willing to work behind the scenes, within the system.
Eight years ago, Obama, a little-known state senator, mounted an upstart challenge to four-term incumbent Bobby Rush for his U.S. House seat. Jackson endorsed Rush. President Clinton also joined the effort to stop the newcomer. He overrode his policy of staying out of Democratic primaries to back Rush, who trounced Obama more than 2-to-1.
"I already had a relationship with Bobby Rush," Jackson said Friday in an interview with Associated Press television.
That's not the only time Jackson was in Obama's way. In 1995, he tried to arrange for his son to get the state Senate seat that Obama eventually won in his first political race.
Jesse Jackson Jr. told The Associated Press that his father wanted the incumbent to run for Congress so the younger Jackson could replace state Sen. Alice Palmer. She refused to go along because she was supporting Obama, who hadn't announced his campaign to succeed her yet. Jackson's son also rejected the plan and successfully ran for Congress instead.
The younger Jackson, 42, has become a close friend to Obama, 46. He's a national co-chairman of Obama's campaign.
Late last year, Jesse Jackson Jr. even fussed at his father for writing a column questioning the commitment of Obama and other Democratic candidates, except John Edwards, to the needs of black voters. The son wrote a response in The Chicago Sun-Times with the headline "You're wrong on Obama, Dad."
The dueling newspaper columns illustrate the dangers the elder Jackson represents for Obama.
Criticism from the civil rights leader could undercut Obama's strong support among black voters. But too enthusiastic an embrace by Jackson might weaken Obama's efforts to present himself as a new kind of black politician.
Their histories reflect the changing realities between the 1960s and the 1980s for a black man seeking to become a political leader.
Jackson, a minister, was already on Chicago's South Side when Obama moved there in 1985. Jackson had a rare ability to rally people to action. He had used it to put together Operation PUSH in Chicago, then to transform himself from a Chicago civil rights protest leader to a national figure who traveled the country to confront private companies or public officials he felt oppressed minorities or poor people.
He also became a volunteer diplomat who traveled to Syria and Cuba where he won the release of U.S. prisoners. He was welcomed and thanked at Ronald Reagan's White House.
When he first ran for president in 1984, Jackson failed to win the Democratic nomination but still waged the most successful campaign by a black candidate up to that time. He emerged as an important but controversial figure in Democratic politics.
He had called New York City "Hymietown." He met with Mikhail Gorbachev and Pope John Paul II. He hosted "Saturday Night Live."
After his second presidential campaign, he electrified the 1988 Democratic national convention with his appeal to "Keep hope alive!" But he never came close to being president.
Getting his political start in Chicago, Obama didn't choose a public role at the head of civil rights marches but rather the quiet, behind-the-scenes position of community organizer, teaching poor people how to unite so they could step forward themselves.
While Jackson was thinking nationally and internationally, Obama was focused on Chicago's far South Side. The area's working class was disappearing in the wake of steel plant closings. Healthy neighborhoods had decayed into collections of empty storefronts that lacked the political clout to get their share of city services.
Obama's focus was on getting potholes filled, parks cleaned up and students placed in summer jobs. Politically, he paid more attention to the city's first black mayor, Harold Washington, than to Jackson.
When Obama expanded his horizon beyond Chicago, he went to law school, came back and later ran for the state Legislature.