Awkward Past: Jesse Jackson and Barack Obama

There was a time when Jesse Jackson and Barack Obama were, to all appearances, good friends. In the '90s, as Obama was rising in Illinois politics, he and Jackson would often attend community events and fund-raisers together. They went out to dinner and invited each other to family birthday parties.

In private, though, the relationship was more complicated, and not as close as it seemed. The men had different approaches to politics: Jackson was old school, an unyielding civil-rights-era fighter ever on the lookout for injustice to denounce. Obama—like other younger black politicians who came up after Jim Crow—was less heated, a results-oriented pragmatist who was willing to compromise and who saw the old guard's combative style as obsolete. Obama did not consider the reverend as his mentor; when Obama ran for Congress in 2000, Jackson backed his rival. Yet Obama was careful not to push Jackson away. He was a powerful figure in Chicago, a man better to cultivate than alienate.

Now it's Jackson who has to worry about alienating Obama. After Jackson—foolishly assuming his mike was off between segments on a TV talk show last week—was caught whispering to another guest that he wanted to "cut [Obama's] nuts off" for "talking down to black people," he quickly turned contrite. He said his words were "crude and hurtful." But it was clearly more than just a vulgar offhand remark. As Jackson saw it, Obama's recent comments urging black men to take more responsibility at home were themselves vulgar—not because Obama's sentiments were necessarily wrong, but because Jackson seemed to believe the candidate was publicly demeaning blacks to win favor with whites. In that brief whisper, Jackson conveyed both his own long-simmering misgivings about Obama's style of politics, and the misgivings of one generation of black leaders about the next.

"It's unfortunate that it had to come out this way, but it did have to come out," the Rev. Al Sharpton tells NEWSWEEK. "There's definitely a generational divide going on in the black community, and it's been happening for a while. People who deny it aren't seeing clearly."

Nowhere is that divide more visible than in the relationship between Jackson, 66, and his 42-year-old son, Jesse Jackson Jr. While Jackson Senior somewhat tepidly endorsed Obama's candidacy, Jackson Junior, an Illinois congressman, serves as a national co-chair of the campaign. Last week he delivered an extraordinary rebuke to his father, saying he was "deeply outraged and disappointed in Reverend Jackson's reckless statement." Jackson Junior seemed to take his father's words personally. "Reverend Jackson is my dad and I'll always love him," he said. "He should know how hard that I've worked for the last year and a half [for Obama] … So, I thoroughly reject and repudiate his ugly rhetoric."

Reflecting on the dustup to NEWSWEEK, Rep. Jackson said that his dad's way of doing things is a throwback to another time: "My father and others before him came out of a different tradition and the rules were different, because it was a different game. Sometimes I think the older school loses sight of that. But the point was for us to get to this place, where we were elected to our positions, and that also means following the rules as they are."

But for the Reverend Jackson, the generational differences with Obama may be as much personal as political—the lament of an elder who believes that he has not been given his due. Friends of Jackson Senior, who asked not to be named talking about private matters, say that the relationship between Jackson and Obama soured as Obama gained stature. Jackson believed Hillary Clinton would win the Democratic nomination. When Obama surged, Jackson began to criticize Obama in public—saying, for example, that John Edwards was a better champion of the poor. "It all comes down to Jesse feeling like Obama didn't really reach out to him for advice during this period," says one of the reverend's friends. "He had run for president and done well. He thought that that should have meant something."

Jackson himself has hinted at these feelings. In an interview with NEWSWEEK last year, he said he rarely spoke to Obama, even though the senator's campaign office wasn't far from his house. "I see the motorcade, so I know when he is in town," Jackson said. In an interview last week, he complained that "we live in an ahistorical country where people don't want to remember or think about what's come before." One of the things people don't remember, Jackson said: his own presidential campaigns in 1984 and 1988, which he believes helped break ground for Obama. "We made great strides in '88," he said. "We beat [Al] Gore and [Dick] Gephardt in areas in Iowa and brought out voters that never felt they had a reason to vote before. These things happened and it is a part of the Obama win as well."

If Jackson can seem wistful about his diminished prominence, he wants it known that he isn't trying to cause trouble for his party or weaken the nominee. "It is ridiculous to think I have any resentment or jealousy toward Obama or any other younger person coming up," he said. "I made a serious mistake … But why would I be jealous? I'm part of the winning team."

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