Obama's artful corralling of the Jesse Jacksons.

In 2002, Barack Obama was an unknown Illinois state senator with long-shot ambitions of moving from the political backwater of Springfield to the big-time of Washington, D.C. But, before he acted on those ambitions, he wanted to get the blessing of another young, black––and far more famous––Illinois politician, one whom he essentially hoped to leapfrog on his way to the U.S. Senate. And so, one morning that year, Obama had breakfast with U.S. Representative Jesse Jackson Jr. “Barack asked if Jesse planned to run for the Senate seat [in 2004], and, if Jesse did, then Barack said he wouldn’t,” recalls Frank Watkins, a longtime political adviser to the Jackson family who was the representative's press secretary at the time. “But Barack said that, if Jesse wasn't planning to run, then he intended to run. Jesse told him to go ahead and run for the Senate. ... The rest, as they say, is history.”

Of course, Jackson had good reason to forego a Senate campaign of his own––a fact of which Obama was certainly aware. Although the representative had built a biracial coalition in his Chicago-area district, the Jackson name was still mud among many white voters in other parts of Illinois––especially after 1999, when Jackson's father, the Reverend Jesse Jackson, was arrested for protesting the expulsion of six black students from a Decatur high school. In other words, the prospects of Representative Jackson winning a statewide race were dim.

But Obama’s gratuitous display of deference paid off. Although the younger Jackson and Obama had once been viewed as rivals, the former now threw his full support behind Obama's Senate candidacy––co-chairing his campaign committee, doing a billboard ad on his behalf, and even sharing a campaign office with him. Just as important, Reverend Jackson followed his son's lead and stumped for Obama, touting him as “a black man of substance.” For a politician whose mixed-race background had raised doubts among some African American voters––in 2000, Illinois Representative Bobby Rush, a former Black Panther, successfully fended off a primary challenge from Obama by intimating that Obama wasn't “black enough”––the backing of the Jacksons in 2004 was crucial.

As that episode shows, Obama has been quite shrewd in managing his relationship with the Jackson family. And now, in his presidential campaign, Obama once again has endorsements from the two most prominent Jacksons. But the elder Jackson has been far less supportive of Obama than his son. And other members of the family are actively opposing the first African American candidate with a realistic shot of getting to the White House. The reverend’s wife, Jacqueline, has done a radio ad for Hillary Clinton in South Carolina, and Jesse Jr.’s brother Yusef helped organize a Hillary fund-raiser in Chicago. The resulting drama has been seen as a sign of an epic struggle over leadership of the country's black community. But, in reality, Obama’s complicated relationships with the Jacksons have less to do with black politics than they do with Chicago politics and the family politics of America’s most famous black political clan. Unfortunately for Obama, that doesn't make those relationships any less significant––or potentially damaging––to his presidential campaign.

AS A YOUNG MAN, Obama considered Jesse Jackson Sr. a hero. In his memoir, Dreams From My Father, Obama wrote of how, as a student at Columbia in the early ‘80s, he would go to Harlem to hear Jackson speak. And, in a recent interview with New York, Jackson said Obama once told him that it was his 1984 presidential bid that made the young Obama believe his own dream of eventually running for the White House “was really possible.”

But, after college, Obama tried and failed to get a job with a civil rights organization and instead drifted toward the competing social justice theories of the radical community organizer Saul Alinsky. In 1985, Obama found work as a community organizer on Jackson's home turf of Chicago, but it was another African American politician––Harold Washington, who had been elected mayor in 1983––whose presence lured him there. By the time Obama was president of the Harvard Law Review in 1990, his opinion of Jackson had deflated enough that he amused classmates with an impersonation of the reverend.

When Obama returned to Chicago after law school, however, he presumably abandoned the Jackson jokes––part to preserve domestic tranquility. His wife, Michelle, grew up on Chicago's South Side and went to a magnet high school with Santita Jackson, the reverend's oldest child. Frank Watkins remembers frequently seeing Michelle at the Jacksons' house in the ‘70s when he'd go there to play basketball with the reverend. “Michelle and Santita kind of babysat for Junior and Yusef and Jonathan [the third Jackson son] and oversaw the kids when the parents were gone,” Watkins says. When the Obamas were married in 1992, Santita was a bridesmaid and Jesse Jr. (who once half-jokingly confessed to having had a boyhood crush on Michelle) was one of the only 100 or so guests at their wedding. In a way, the Jacksons were now part of Obama’s family.

As an aspiring black politician in Chicago, though, Obama had more pragmatic reasons for getting on Reverend Jackson's good side. So Obama worked to cultivate the relationship. After spearheading a successful voter registration drive that added 150,000 Chicagoans to the rolls in 1992, Obama made sure that Jackson got the glory. John Schmidt, a Chicago lawyer who was a fund-raiser for the effort, recalls, “I was struck when they announced the results that Barack really did allow Jesse Sr. and some others to stand up and take credit for it.” According to Dan Shomon, a Chicago political consultant who managed Obama’s early campaigns, Obama also became a regular presence at Jackson’s Rainbow/push organization, walking the half-mile from his South Side home to the group’s offices on Saturday mornings to hear Jackson give his weekly speech. “He went to so many push meetings,” Shomon says. “That’s the thing people don't give Barack credit for. He’s really a workmanlike politician.”

But Obama abandoned his workmanlike approach toward the elder Jackson when it came to his presidential bid. “He didn’t work very hard to get the endorsement,” says Ronald Walters, a University of Maryland political science professor and Jackson confidant. “I know he didn't ask for it. ... And Barack hasn't acted like [Jackson’s] endorsed him in any way, acknowledging him publicly or having him on the trail.” Jackson seems to have taken all of this as a slight, because, after offering Obama his apparently unsolicited endorsement last March, he’s repeatedly undercut it––complaining to a South Carolina newspaper in September that Obama was “acting like he's white” and penning an op-ed for the Chicago Sun-Times in November that blasted every Democratic presidential candidate save John Edwards for “virtually ignor[ing] the plight of African Americans in this country.” Even Jackson's friend, Chicago political consultant Don Rose, wonders “whether Jesse Sr. might harbor a little jealousy because of where Barack has come from and sort of sees him as someone who has, in many ways, surpassed him in politics.”

JESSE JACKSON JR. would seemingly have good reason to envy Obama, too. Once considered one of the––if not the––most prominent young black politician in the United States, Jackson now can’t even claim that honor in his hometown. But, if Junior has any resentment toward Obama, he’s hiding it well. He's a national co-chair of Obama's presidential campaign and has stumped for him across the country. “Jesse’s really helping him, because Barack doesn't have time to energize the black community in any of these states, because he’s got to energize women, he’s got to energize independents,” says Shomon. "Jesse Jr.’s playing the number-one role of energizer.”

He’s also Obama's number one defender against other Jacksons. The radio ad Jacqueline Jackson cut for Clinton in South Carolina shared airtime with one from Jesse Jr. singing Obama's praises. He has touted Obama’s fundraising success to reporters, perhaps as a way to offset the $100,000 raised for Clinton by his brother Yusef (whose support for Hillary presumably has something to do with his business partner, California billionaire and Clinton pal Ron Burkle). And, most notably, Junior responded to his father’s Sun-Times op-ed with a letter to the editor that was headlined, “you're wrong on obama, dad.” According to a Democratic strategist, that’s a message Jackson has delivered privately––and more forcefully––as well. “The congressman told me he had a few words with his dad,” the strategist says. “He basically said, ‘I smacked him down.’”

Indeed, the younger Jackson seems to have realized that, by helping Obama, he can help himself. While Junior may have once harbored national ambitions, he’s recently begun building a political machine in Chicago that many local observers believe he’ll ultimately use to run for mayor. Obama has become an integral part of that machine. His presence on the ballot in the February 5 Illinois primary will undoubtedly boost black turnout in Chicago––which, in turn, should help the candidates Jackson is backing in local races (including Jackson's wife, Sandi, who was elected to the city council last year). Obama's helping Jackson in more direct ways, too. In one hotly contested state House race on Chicago's South Side, a former Obama aide is running against a Jackson-backed candidate. Although Obama was expected to endorse his former staffer, he has so far remained neutral. And, if Obama became president, some speculate Jackson would be in line for a Cabinet post. At the very least, Obama would no longer be a potential rival in Chicago.

But the alliance between Obama and Jesse Jr. may actually be too successful. After receiving the smackdown from Junior, Reverend Jackson has become much more on-message about Obama––praising him in interviews and even inviting him on his radio show the day before the Martin Luther King holiday. And that, in a way, could hurt Obama. After all, there's a reason Obama didn't actively seek the elder Jackson's endorsement for his presidential bid. As Ronald Walters sees it, “His campaign has tried to neutralize the issue of race.” But, as the Clintons cynically try to marginalize Obama as the “black” candidate, the support he receives from Jackson Sr. may only serve to help them in those efforts. At the start of his campaign, Obama presented himself as an antidote to Jesse Jackson Sr.––a black presidential candidate who could actually win. His opponents hope that, in defeat, he'll wind up being Jackson's heir.

This article appeared in the February 13, 2008 issue of the magazine.