When Jesse Jackson Jr. walked into a Washington, D.C., federal courthouse in February to plead guilty to federal charges of looting his campaign fund of $750,000, Capitol Hill insiders held a similar reaction.

What could have been?

From the time the Chicago ex-congressman took office, bets were wagered on how high his star would rise: Mayor of Chicago? U.S. Senate?

“I have no other office in mind besides where I’m at now,” Jackson insisted in 1996. “This is my magnificent obsession.”

Seventeen years after he was first elected, Jackson’s “magnificent obsession” has taken on a new meaning.

He — with the help of his wife, Sandi — indulged in mink capes, pricey vacations, mounted elk heads, Bruce Lee and Michael Jackson memorabilia; all illegal purchases with campaign money.

“Jr.,” as he is often referred to, was the first in the Jackson political dynasty to be elected to office. His image nationally was one of a great and powerful orator, someone who could break barriers, make history — maybe outshine his father’s sometimes controversial legacy.

For people in Chicago and closer to the boiling pot of corruption bubbling up from Springfield since the days of Rod Blagojevich, Jesse Jackson Jr. seemed to unravel in slow motion.

It began in 2008, when Blagojevich was spectacularly arrested and federal prosecutors revealed the FBI had been recording him for the prior eight weeks.

The criminal complaint made public that day quoted then-Gov. Blagojevich, who believed he would receive a $1.5 million campaign donation if he appointed “Senate Candidate 5” to the U.S. Senate position left vacant by Barack Obama’s election as president.

In recordings, Blagojevich is overheard talking about how he might be able to cut a deal with Candidate 5 and wanted “something tangible up front.”

It didn’t take long for the public to figure out that Jackson was the unnamed Senate Candidate 5 in federal documents.

Jackson immediately shot down any shady connection to the Blagojevich case, making clear that Blagojevich was citing an interaction the former governor had with someone else — not Jackson.

Charging papers described that person as an “emissary” to Jackson.

Jackson was adamant from the beginning that he never authorized anyone to offer a quid pro quo on his behalf.

“I thought, mistakenly, that the process was fair, above-board and on the merits,” Jackson said during a news conference at the time. “I thought, mistakenly, that the governor was evaluating me and other Senate hopefuls based upon our credentials and qualifications.”

Enter Raghuveer Nayak.

Nayak was a wealthy businessman who owned surgical centers in Illinois and Indiana and was active in Chicago’s Indian-American community. Nayak traveled to India with Rev. Jackson once and was a longtime friend of the Jackson family.

A regular political donor, he had insider access to politicians, including Jackson Jr.

Nayak was the so-called emissary whose involvement in the case would end up acting as a backdrop to more than one Jackson story line.

Jesse Jackson Jr. is the oldest of the Rev. Jesse Jackson’s three sons. He co-wrote books with his father, had a strong knowledge of history, and his speeches were so stirring that he once commanded high speaking fees.

A May 1996 Chicago Magazine piece went inside the Jackson patriarch’s home, noting that so much history had happened in that house, with his family surrounding it. Jackson Sr. ran for president in 1984 and 1988 and launched the Rainbow Push Coalition, which continues today in Chicago.

“The persistent presence of political discussion right in their own home meant the Jackson children were trained to think about world issues and business concerns early on and exposed to the kind of people their parents hoped they would someday become,” the article noted.

In his politically formative years, Jackson Jr. obtained a law degree and honed a career as an activist by working for labor causes and against apartheid in South Africa.

What the Chicago Magazine piece also described, however, was a family life that grew progressively privileged. While the Rev. Jackson had a reputation of fighting for the unemployed, the repressed, the poor — the Jacksons themselves lived well. They vacationed at Hilton Head and Disney World and even jetted off on spur-of-the-moment trips.

“Once while attending law school, Jesse Jr. received a midweek call from his father inviting him to jet to Las Vegas to watch Mike Tyson fight. The trip took less than 24 hours, putting him back in class the next morning with the same students he’d left the afternoon before,” the magazine article states. It quotes Jackson Jr. saying: “When I told them, ‘I was at the fight last night,’” he recalls with obvious relish, “they said, ‘No way.’”

In 1995, Jackson ran for Congress after the officeholder — Mel Reynolds — was convicted of having sex with a 16-year-old campaign worker, as well as of bank fraud. Jackson won his election and at the time, articles lauded his use of technology and broad campaign army that knocked on doors throughout the district.

Jackson’s trajectory, however, grew static at the same time that another African-American pol, who didn’t have half the pedigree of the Jackson dynasty, rose to stardom.

He was Barack Obama. Obama went from state senator to the U.S. Senate, and his popularity was skyrocketing as other state politicians with lofty aspirations — Blagojevich and Jackson Jr. included — grew frustrated.

When Rod Blagojevich was granted the sole power to appoint Barack Obama’s successor to the U.S. Senate, Jackson Jr. saw his big break coming.

He launched a campaign. He paid for polling. He lobbied for newspaper endorsements. He directed supporters to barrage Blagojevich’s office to lobby for Jackson’s appointment, saying he was the most qualified to serve because of his years in Washington.

Jackson met with Blagojevich the day before the governor’s arrest to laud his accomplishments. He also apologized to his former fellow congressman for not endorsing him when he ran for governor. Blagojevich had harbored a grudge against Jackson for years because he said Jackson had promised to endorse the former governor, boosting his ability to get the black vote in Chicago. Jackson, though, changed his tune and endorsed former Illinois Attorney General Roland Burris because he said he felt he had to support an African-American.

All this activity — legal activity — was as far as Jackson went, by his own account.

However, a man close to Jackson, the same man whom Jackson trusted with at least one personal secret, told a different story.

In 2010, the Sun-Times reported that Raghu Nayak told the FBI that Jackson had directed him to approach the Blagojevich camp with a $6 million offer for the Senate seat. Nayak said he told Robert Blagojevich, the governor’s brother, that the Indian-American community in Chicago would raise $1 million right away, and then Jackson, once he was in the Senate, would raise an additional $5 million for the governor. Robert Blagojevich, who testified at trial to the same set of facts, rejected the offer.

Rod Blagojevich, though, resurrected the possibility weeks later —when FBI tapes were rolling.

Nayak said Jackson asked him to make the approach while Nayak visited Washington from Chicago. Nayak told the FBI that he, Jackson and a female “social acquaintance” of Jackson dined together and enjoyed cocktails that night.

Jackson would later ask Nayak to secretly pay to fly the woman, a Washington hostess and aspiring model, to Chicago and back to the East Coast.

When the Sun-Times reported Nayak’s testimony to the FBI, Jackson issued an apology for the social acquaintance. However, he steadfastly denied the pay-to-play allegations that would continue to haunt Jackson under the looming Blagojevich cloud.

On June 10, 2012, Jackson disappeared from Congress. But he didn’t notify anyone for two weeks. The notification came at 5 p.m. on the same day as the deadline for those filing to oppose him for the upcoming election.

The news release reported Jackson was leaving the Hill for medical reasons.

“On Sunday, June 10th, Congressman Jesse L. Jackson Jr. went on a medical leave of absence and is being treated for exhaustion,” the statement read. “He asks that you respect his family’s privacy. His offices remain open to serve residents of the Second District.”

His wife, Sandi, then 7th Ward alderwoman, later told the Sun-Timesthat he had collapsed at home.

His strange disappearance continued for months. The congressman did not appear publicly; he did not put out personal statements. The public did not hear from Jackson from June until the end of November — with the exception of a robocall released to constituents of his district right before the Nov. 6 general election.

By contrast, Republican U.S. Sen. Mark Kirk — who suffered a stroke a year earlier, had a highly sensitive surgery to relieve swelling in his brain, endured a rigid routine to learn how to walk again and underwent speech therapy — regularly put out videos showing his physical progress. Kirk, too, released statements and videos endorsing other candidates. He spoke via prerecorded video to the Illinois delegation at the Republican National Convention.

Jackson, on the other hand, was completely silent. As the months wore on, the chorus demanding answers grew louder. What was the nature of his illness? Was he going to resign?

Eventually, it became public that Jackson was receiving treatment at Mayo Clinic in Minnesota. A statement was released describing his illness as bipolar depression.

It was before Jackson took that leave that something else was happening completely unknown to the public: The FBI was poking around his finances. Agents didn’t like what they were seeing.

Jackson was clearly living well beyond his means. There was suspicious movement in his campaign account. There were high-volume credit card charges with suspect expenditures.

The Sun-Times previously reported that federal authorities believed Jackson knew of the investigation before his June 10 departure from Congress.

Jackson did not campaign, and two long-shot opponents called for him to show up to campaign or resign.

Jackson never responded and never showed up. But he easily sailed to victory, with a core of loyal voters from the 2nd Congressional District who for so long had counted on the Jackson name to help boost their communities.

Fifteen days later, Jackson resigned.

It was only then that Jackson admitted to something that had been reported a month earlier — he was under federal investigation.

In his resignation letter, Jackson ran through his accomplishments.

“We have built new train stations, water towers and emergency rooms. We have brought affordable housing, community centers and health care clinics to those that need it most,” he wrote. “In all, nearly a billion dollars of infrastructure and community improvement has been made on the South Side of Chicago, and thousands of new jobs have been created.”

Still, there was something else he admitted for the first time.

“During this journey I have made my fair share of mistakes. I am aware of the ongoing federal investigation into my activities and am doing my best to address the situation responsibly, cooperate with the investigators and accept responsibility for my mistakes, for they are my mistakes and mine alone,” he said. “None of us is immune from our share of shortcomings or human frailties, and I pray that I will be remembered for what I did right.”

Last month, President Obama was on hand during a historic dedication of Rosa Parks’ statue in Statuary Hall in the U.S. Capitol. At one point, he made his way into the crowd of onlookers and strode directly to two young kids. USA Today snapped a photo of Obama hugging one of the kids and put it on its front page without names in the caption.

The girl he was hugging was Jessica, Jesse Jackson Jr.’s 13-year-old daughter.

A boy’s profile also clearly captured in that photo was Jackson’s son, Jesse Jackson III, who’s also called Trey.

The Jackson children attended the dedication, along with their grandparents — the Rev. Jesse Jackson and his wife, Jacqueline — but the then-resigned congressman’s absence was notable. Jackson Jr. had initiated the legislation that would move the Rosa Parks statue into that hall.

The dedication had been postponed until Jackson returned from a leave he took the prior June. When it became clear he wasn’t returning to Congress, it moved forward.

Before his leave, however, Jackson had penned a speech that touched on the historical significance of the hall having been the place for many of the nation’s great debates, including over slavery.

Jackson’s remarks talked about a reverence for the law and Parks’ impact on civil rights.

“To put it another way, paraphrasing a past popular song, Rosa Parks fought the law (state and local law) — and the law (federal law) won — by affirming everyone’s citizenship and providing equal protection under the law for all Americans.”

“Rosa Parks — rest in peace,” Jackson’s speech was to close: “Stand here among the mighty, with dignity.”

Natasha Korecki is a political reporter for the Chicago Sun-Times and author of Only in Chicago: How the Rod Blagojevich Scandal Engulfed Illinois; Embroiled Barack Obama, Rahm Emanuel, and Jesse Jackson, Jr.; and Enthralled the Nation.

Illinois Issues, April 2013