Four years later, when Obama ran for president, Jackson was there to help again. He leaned heavily on his fellow members of the Congressional Black Caucus to support Obama, going so far as to threaten primary challenges against those who’d endorsed Hillary Clinton—a move that particularly rankled older black congressmen, like Charlie Rangel and John Lewis, who’d known Junior since he was a child. But Jackson’s biggest battles on behalf of Obama were with members of the Jackson family, many of whom were supporting Clinton. When his mother Jackie cut a radio ad for Clinton in South Carolina, the Obama campaign had already aired one that Junior made there; he also worked to raise money for Obama in order to offset the $100,000 his brother Yusef raised for Hillary.
Jesse Jr.’s thorniest task was managing his father. Although the reverend had endorsed Obama, he didn’t always act like it—complaining to a South Carolina newspaper that Obama was “acting like he’s white” and, most infamously, being caught by an open mike saying that “I want to cut [Obama’s] nuts off” for “talking down to black people.” In public, Jesse Jr. was blunt with his push back, saying that he was “deeply outraged and disappointed in Reverend Jackson’s reckless statements” and that his father “should keep hope alive and any personal attacks and insults to himself.” Privately, he was even more pointed in what he said to his father, telling one Democratic strategist, “I smacked him down.” By the time Obama was elected, there was so much ill will in the Jackson family that Jesse Jr. and his younger brother Jonathan, best friends since childhood, were barely on speaking terms.
But Obama and his advisers did not reward that loyalty by helping Jesse Jr. get what he most wanted: Obama’s Senate seat. Shortly before the election, Obama dispatched emissaries to tell Blagojevich that he hoped the governor would appoint his adviser and friend Valerie Jarrett—and that Obama explicitly didn’t want the seat to go to Jesse Jr. Indeed, Obama’s aversion to Jesse Jr. was so pronounced that Blagojevich and his aides eventually came to view appointing Jackson as a way to punish Obama for not offering Blagojevich anything in exchange for appointing Jarrett. “That would be revenge,” one Blagojevich aide told his boss.
Part of the Obama team’s reluctance about Jackson was political. Obama’s advisers were never sold on the idea that Jackson could hold on to the Senate seat when it came up for reelection in 2010. “They put Jesse in the box of being an urban black politician, of being Jesse Jackson’s son, who couldn’t win a statewide race,” says one person who participated in conversations with the Obama team about the Senate appointment. But it also may have been personal. “I don’t think Barack ever trusted Jesse,” says one Illinois Democrat, who was friendly with both Jackson and Obama. “He was just suspicious of him.”
The suspicion was mutual—and perhaps inevitable. One prominent Illinois Democrat remembers running into Jesse Jr. at the 2004 Democratic convention the morning after Obama’s keynote address: “We knew something special had happened, and everyone from Illinois, especially everyone from Chicago, was happy—everyone except Jesse. He was like, ‘What the fuck? This guy just hurdled over me.’ ” Once considered the most prominent young black politician in the United States, Jackson could no longer even claim that honor in his hometown.
After Obama failed to go to bat for Junior on the Senate appointment, or offer him a job in the administration, that suspicion curdled into outright bitterness. “He seemed very sore at the president,” one person who discussed the matter with Jackson says. “He felt the president really just forgot him and kind of left him out. Junior viewed himself as having made a king and people, including the king himself, didn’t appreciate that.”
On Saturday, June 10, Jackson appeared from Chicago, via satellite, on Melissa Harris-Perry’s MSNBC show. He was touting a bill he had just introduced to raise the minimum wage. “This is not welfare,” Jackson said. “These are people who are working hard every day, and at the end of a hard day’s work, they can’t keep up with the Consumer Price Index.” That afternoon, after Jackson had flown back to Washington, he called Watkins to check in. “He was talking about, ‘Man, the minimum-wage thing is driving these right-wingers crazy,’ ” Watkins says. “He was really pumped up about that.”
But that evening, Jackson’s mood apparently darkened. According to an account his wife, Sandi, later gave to the Chicago Sun-Times, Jackson was in his Dupont Circle home by himself. (Sandi and the couple’s two children were in Chicago.) “His father, Reverend Jackson, called him on the phone and felt he didn’t sound right,” Sandi told the newspaper. “Jesse told his father he was so exhausted, he couldn’t take another step.” It was then that the Reverend Jackson and Jesse Jr.’s brother Yusef went to the congressman’s house and rushed him to George Washington University Hospital.