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Jesse Jackson Jr.’s Dark Days

Once one of the most promising politicians in the nation, Jesse Jackson Jr. has seen his career go horribly wrong—marked most recently by his mysterious disappearance and the revelation that he’s suffering from bipolar depression. What happened to Junior?

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Jackson with his children at his wife’s 2007 victory party. For more photos, launch the gallery »

Jackson’s reputation as a reformer first took a hit when he helped elect his wife to the City Council in 2007. It smacked of the kind of friends-and-family politics practiced more readily by his political foes, even if Sandi had already been immersed in national politics, including positions at the Democratic National Committee and a senior post at the Export-Import bank (appointed by Bill Clinton).

The couple met in D.C. in 1988, when Sandi worked as the press secretary for the Texas congressman Mickey Leland. She left to attend law school at the University of Illinois with her future husband. Afterward she set up a political consultancy in Chicago from which she helped build Jackson’s organization. “Her ascension really became a part of a plan that Jesse Jr. had to establish a political beachhead,” says a former Jackson confidant who requested anonymity. “And he very methodically went about plotting, diligently and successfully.”

Jackson invested just over $87,000 from his congressional coffers in Sandi’s campaign. That was about a third of all the money raised to defeat Darcel Beavers, the incumbent 7th Ward alderman—who herself had been installed by her father, the longtime alderman Bill Beavers. (Jackson has since contributed another $164,000 to his wife’s campaign fund.)

Even as alderman, Sandi continued to draw a paycheck from her husband’s campaign fund. (She has made at least $275,000 since she took the seat in 2007 and nearly $450,000 since 2002.) The couple received a ruling from the Federal Election Commission saying that the practice was legal. But that didn’t mean it didn’t smell fishy. Critics accused Jackson of converting campaign contributions to personal income. It didn’t seem to bother him.

“The best way to describe both of them,” says a former associate, “is that they are very out of touch with reality, living in their own fantasy world.” The D.C. Office of Tax and Revenue values their Washington home, off ritzy Dupont Circle, at $1.3 million, and Jackson Jr. has a well-documented taste for BMWs. One of the first things Sandi did upon taking office was grouse publicly about her aldermanic expense allowance of $33,280 a year. She promptly held a fundraiser and took in $50,000.

The Jacksons’ marriage seemed picture-perfect, though it was unconventional even by political-marriage standards. They often spent time apart, he in Washington, she in Chicago, with little overlap. (Sandi’s mother frequently looked after the children.) But Jackson’s affair with Huidobro, revealed by the Sun-Times in September 2010, two years after the relationship had supposedly ended, exposed deep fissures.

With their marital problems front-page news, Sandi went into damage control mode, going public to “discuss her private anguish.” (Her husband was not made available to answer questions.) While Sandi said in an interview that she “put her foot knee-deep in [Jesse’s] ass because I wanted everyone to know I was not taking it lightly,” sources say it wasn’t the first time her husband had strayed. “It’s not because he’s not happy with Sandi; they have a great relationship,” one source who used to be close to Jackson explains. “It’s to feed his insecurities. Guys who are insecure need to have that validation.”

Jackson needed validation in his political life too—and despite his mixed feelings about Obama’s rise to the White House in 2008, it opened up a new opportunity for his career. Somebody had to fill Obama’s Senate seat, and Jackson figured it should be him. He was reenergized, one source says: “I sensed Jesse reached for the Senate seat out of being awakened.”

Jackson would have been a logical pick. He had been a congressman for 13 years with nary a whiff of scandal (news of his extramarital affair had yet to break); he was a gifted orator; he was a friend of Obama’s who also hailed from the South Side; and he would retain the only African American seat in the Senate.

But as Jackson presumably knew, Governor Blagojevich wasn’t planning to appoint someone on merit or even qualifications. The governor was trying to leverage his appointment power for political and personal gain. Worse for Jackson, Blagojevich harbored a deep loathing for him, apparently because Jackson recanted his endorsement of Blagojevich in the 2002 governor’s race after Roland Burris entered the contest. (Ironically, the governor, as we all know, wound up appointing Burris as Obama’s replacement.)

Usually when it comes to seeking political appointments, good politicians follow the template set down by successful vice presidential wannabes: Don’t let on how badly you want the job, but let on just enough to make it clear that, if asked, you’d take it.

Instead, Jackson built a public case to pressure the governor into choosing him. He chatted up as many reporters as he could, spoke to editorial boards, encouraged a letter-writing campaign, and commissioned his wife to conduct two polls. One indicated that Jackson led all prospective Senate candidates with the support of 21 percent of those surveyed. The other showed that Sandi would be an overwhelming favorite to succeed her husband in the House.

To the rest of the political establishment, Jackson’s aggressiveness was unsenatorial, even unseemly. “That period of time, it was problematic,” recalls Kwame Raoul, the state senator who now holds Obama’s old seat in the General Assembly. “There were a number of people who had interest, a number of congressmen and others, but he was the most visible.”

Jackson was unapologetic: “Anyone who is not campaigning for this office in one form or another is not taking the process as seriously as it has to be taken,” he said in a TV interview.

At the 2008 Democratic convention in Denver, Jackson’s quest for the seat became a piece of pure theatre. Rising to speak in a room filled with Illinois’s most powerful political figures, Jackson put away his prepared remarks, teared up, and called for a grand reconciliation, which saw him hugging congressional rivals Bobby Rush and Debbie Halvorson as well as Mayor Daley.

It seemed bizarrely genuine at the time. But, looking back, one could wonder if the hug-a-thon was a stunt to try to consolidate support for his Senate bid. “He really, really in his heart believed he was going to be U.S. Senator,” says Halvorson. “He had to make peace with everyone he had pissed off.”

Denver is also where Jackson first spoke to Raghuveer Nayak about wanting the appointment, according to testimony Jackson gave to the House Ethics Committee. He later downplayed those conversations, saying they mainly consisted of Nayak jokingly calling him “Senator.”

The Indian-born businessman first entered the Jackson family orbit as a supporter of Operation Push. He befriended Jackson’s brother Jonathan and they partnered on several business deals, including the development of a South Side bank building.

It’s unclear how close Nayak was with Jackson. But there is no question that Nayak and another business associate, Rajinder Bedi, once the state’s chief trade officer, offered $1.5 million—perhaps upward of $6 million—on Jackson’s behalf to Robert Blagojevich, who handled fundraising for his brother. The question is whether Jackson knew about or even directed it. (An August 2009 report by the Office of Congressional Ethics found “probable cause” to believe that Jackson had either directed Nayak to make a pay-to-play offer with Blagojevich or knew of the plan.)

Blagojevich was captured on federal wiretaps frequently telling his advisers that the idea of appointing Jackson was “repugnant” to him. But as his options seemed to dwindle, Jackson became more central to his thinking. “I can’t believe anything he says,” Blagojevich comments on one wiretap. “[But] what he’s got third parties saying to me is a heck of a lot more substantial than what we’re getting from the Obama people, OK?”

While Blagojevich worked his end, Jackson worked his, though he was feeling “increasingly disillusioned” with the governor, according to the House Ethics Committee report. Blagojevich was similarly annoyed with Jackson. Here he is talking with the deputy governor, Bob Greenlee, on October 31, 2008:

BLAGOJEVICH: I got some lady callin’ my house for Jesse Jr. here a little while ago.

GREENLEE: I’m tellin’ ya that guy’s shameless.

BLAGOJEVICH: Unbelievable, isn’t it? Then I, we were approached, pay-to-play. That, you know, he’d raise me five hundred grand, an emissary came, then the other guy would raise a million, if I made him a senator.

GREENLEE: I’m not, I’m, ah, you know I’m not surprised by him at all.

On November 10, Blagojevich was clearly reassessing. He told another adviser: “Um, I’ll tell you about this conversation I had with the Jacksons over the weekend. . . . He’s in the mix all of a sudden. OK? . . . I still don’t think I’ll, you know, do it, but he’s, I’m not rulin’ him out now.”

Finally, on December 8, the governor met with Jackson face to face. That meeting took place in a Thompson Center conference room that wasn’t bugged, so we are left without an account that could conceivably settle the matter. What is known is that Jackson brought with him a three-ring binder filled with arguments for appointing him. The last page envisioned a joint campaign in 2010, with Jackson seeking a full six-year Senate term and Blagojevich a third term—though Jackson must have known that the governor, with 13 percent approval ratings, wouldn’t likely be around to see it.

The very next morning, federal agents arrived at Blagojevich’s Ravenswood home and arrested him. When U.S. Attorney Patrick Fitzgerald announced the charges, he said that a scheme to sell the Senate seat was stopped before it could materialize to avoid a constitutional crisis. The scheme appears to be the appointment of “Senate Candidate 5”: Jesse Jackson Jr.

For the next three years, the usually voluble Jackson went into a shell, refusing media requests, dodging reporters, and lobbing his defense only in controlled environments.

But this year, with the Blagojevich trials behind him—Jackson wasn’t called to testify in the first trial, which ended in a hung jury, but did so in the second—he turned his attention to his reelection. Jackson hadn’t faced a serious challenge since first winning his seat in 1995. This time was different—and not just because the Blagojevich albatross around his neck made him vulnerable. He also faced a tough intraparty challenge from his longtime nemesis Debbie Halvorson, she of the Denver hug.

Halvorson had been in Congress herself for a term before being turned out by Adam Kinzinger in the Republican tidal wave of 2010. Before that, she was a four-term state senator who rose to majority leader. Halvorson figured to be formidable, given the additional fact that Jackson’s congressional district had been remapped in the spring of 2011 in a way that benefited her. The redrawn district subtracted Cook County constituents and added more of Will County and even a slice of Kankakee, making it more conservative—and more white.

It was a nasty campaign, but in the end, Halvorson wasn’t up to the challenge. In March, Jackson cruised with 71 percent of the vote. Then he withdrew, to a large extent, from the public eye. And then he disappeared.


Photograph: Terrence Antonio James/Chicago Tribune

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