Jodi Kantor and Monica Davey / New York Times News Service

When Barack and Michelle Obama were married in Chicago two decades ago, Santita Jackson, a daughter of the Rev. Jesse Jackson, sang at their wedding. When Obama ran for his first national office, he made sure he was not stepping on the ambitions of her brother, Jesse Jackson Jr., who later became a co-chairman of his 2008 presidential campaign.

Now the younger Jackson, 47, who served 17 years as a congressman representing his hometown, is most likely headed to prison for campaign fraud, trailed by a string of problems from an extramarital affair to mental illness.

Although the fates of Jackson and Obama could not be more different, their stories, and those of their families, are bound together. The rise of the current leading black political family in the United States is inextricable from the unraveling of an older one, with the two tangled in shifting alliances, sudden reversals of fortune and splits.

Decades ago in Chicago, the younger Jackson was seen as a far more promising figure than his friend Obama — one the heir to a legend, the other an outsider seeking to surpass the father he barely knew.

If Jackson had decided to run for the U.S. Senate in 2004, Obama most likely would not be president. That year and again in 2008, Obama, seeking to bolster his credibility with African-Americans, enlisted Jackson for crucial help.

But along the way, the Jackson father and son helped define what the future president did not want to become: a black politician mired in the old urban-ethnic mold; a leader tainted by personal transgressions or a dysfunctional family.

Now, the Obama administration’s Department of Justice is poised to send Jackson Jr. — who came under investigation after he pursued but failed to obtain Obama’s old Senate seat — to prison.

“The beginning of Jackson’s star being tarnished was the beginning of Obama’s star rising,” Eric Adelstein, a Chicago political consultant, said in an interview. “You can plot it on a chart: As Obama ascends, Jackson descends.”

Ties to the first lady

Decades before Michelle Obama worked on her husband’s presidential campaigns, she volunteered on those of the elder Jackson. Her father, Fraser Robinson, was a city water worker and ward captain, but Santita Jackson, the oldest daughter of the most important black politician in the country, was one of her closest friends; later, Santita Jackson became godmother to Malia Obama, the couple’s older daughter.

“Michelle used to come to the house all the time,” Jesse Jackson recalled in an interview. (The White House declined to comment for this article.)

The man she eventually married was a stranger to Chicago, who had to pound the sidewalks of the South Side to collect signatures to run for a lowly state Senate seat in 1996. Obama would regularly attend weekly meetings of Jesse Jackson’s Rainbow/PUSH organization, and the Jacksons tried to be helpful with advice and opportunities — for example, giving him chances to “get his speaking legs,” said Hermene Hartman, publisher of an African-American newspaper, N’DIGO.

“I don’t think the Jacksons were threatened particularly,” said Don Rose, a longtime political consultant.

Jackson Jr.’s appeal

They had no reason to be. Jesse Jackson Jr. was already a sensation: At just 30, he had defeated more established politicians for a congressional seat. His father proudly raised money and campaigned on his behalf, at one point distributing buttons that read, “a new generation.”

Some in Chicago saw strengths in the younger Jackson that they had not seen in his father — crossover appeal to white voters, expertise in both politics and policy, an ability to move between the civil rights movement and elite institutions like St. Albans, his prestigious Washington school. People magazine even named him sexiest politician.

“If I wanted to be an elected official, that’s not enough,” Jesse Jackson Jr. told The Chicago Tribune in 1995, speaking of the expectations he faced. The jobs he talked about pursuing were mayor of Chicago or speaker of the House, but his father and others went even further, Jackson noted: “‘One day, son, you may be president.’”

It is not clear why he did not run in 2004 for a Senate seat that some thought could be his and gave Obama the go-ahead instead. Some say Jackson had set his sights on other offices; others say he did not think Obama, who had been trounced in a 2000 congressional race, had a chance of winning.

He gave Obama a much-needed endorsement in the Democratic primary. “Jesse had him on 100 billboards,” said the elder Jackson, when Obama’s name “was hardly known.”

Turn of events

Still, Obama was wary of being identified with the older generation of Chicago politics, particularly the elder Jackson, whose fiery civil rights rhetoric often alienated whites and whose reputation was sullied by a messy personal life, including fathering a child out of wedlock.

Campaign aides wanted the Obamas alone on stage the night he won the primary, two of them said later, without other local politicians — especially the elder Jackson, who had a habit of making a beeline for the victor at the moment cameras clicked.

A few months later, when the still-obscure candidate became the toast of the Democratic Party after a soaring speech at the presidential nominating convention for Sen. John Kerry, several people noticed that both Jackson men seemed disoriented by the turn of events.

“They were the biggest thing in African-American politics,” said Jim Cauley, Obama’s campaign manager in the Senate race, and in one night, “they got eclipsed.”

The younger Jackson felt that Obama “was sort of elevated to his status without having to pay his dues or do grunt work,” said Alexi Giannoulias, a former state treasurer. “Which was simply untrue — he worked incredibly hard as a candidate and he did so all across the state, which is something Junior never had to do. But I think in his mind, somewhere deep down, Junior felt that way.”

After that, the younger Jackson appeared to grow even more determined. He transformed himself with weight loss surgery and considered a run against Mayor Richard Daley in 2007.

In the 2008 presidential race, both Jackson men endorsed Obama. But though the congressman served as a co-chair of his campaign, his father openly seethed at Obama, criticizing him at turns for “acting like he’s white,” not appearing at a civil rights anniversary and “talking down to black people.” He made a crass anatomical remark about Obama, unaware that he was speaking on a live microphone.

His son issued a rebuke. “He should keep hope alive,” he said, “and any personal attacks and insults to himself.”

The elder Jackson’s influence was already on the wane, but the hostility he showed toward Obama, who was winning the devotion of black voters, sealed his loss of prestige. Obama’s attitude toward the older man was “I’m bigger than this, so I’m just going to ignore you,” said one fundraiser.

Jackson Jr.’s downfall

Obama’s presidential election victory seemed to create the opportunity the younger Jackson had been seeking. He lobbied hard for Obama’s Senate seat, petitioning Gov. Rod Blagojevich, who would make the appointment; seeking letters of support from opinion-makers; publicizing a poll his camp had commissioned.

Instead, his life fell apart. Blagojevich was arrested, charged with trying to solicit money or a job in exchange for the Senate seat. And a friend of Jackson’s was accused of offering large campaign contributions if Jackson was picked. Jackson denied knowing about the offer, but a House Ethics Committee investigation was opened.

In 2010, revelations emerged of an extramarital relationship. By 2011, few even seemed to think of him as a contender for the job of mayor of Chicago after Daley announced plans to retire. And by June 2012, he disappeared from Congress, his office eventually announcing that he was being treated for bipolar disorder. He resigned in November, and pleaded guilty last week to a felony fraud count for spending campaign funds on living expenses and collectibles.

(On Tuesday, Robin Kelly, whose campaign called for tougher national gun laws, clinched the Democratic nomination in a special primary election for Jackson’s House seat, in a district that heavily leans Democratic.)

Through a spokesman, Jesse Jackson Jr. declined to be interviewed for this article, but he issued a statement apologizing to those he let down.

Where they stand now

Since becoming president, Obama has had dwindling contact with the Jacksons. The son was under investigation and the father was persona non grata, invited to not a single one of the civil rights meetings Obama has held, despite the role that Jackson played in the movement and in helping to clear the way for a black man to become president.

“By the time he came along, he was going across a bridge that came from the rocks of the walls that we knocked down,” the elder Jackson said in the interview.

He had just returned from Washington, where he appeared in court with his son, and he sounded weary. But he discussed the president with none of his old acrimony. Obama, he said, was a “rare genius.”

He seemed to savor the one moment he has shared with Obama in recent years, a quick staged photograph after the dedication of the memorial to the Rev. Dr. Martin Luther King Jr. in 2011.

The Jacksons waited along with other civil rights leaders for their shot with the Obamas, but Jackson described the encounter as a reunion for the two families, who spent a few minutes exchanging pleasantries and memories.

He said he spends little time worrying about his standing at the White House or invitations there, adding, “I give him room to govern.”

Jesse Jackson Jr. will write a memoir

Jesse Jackson Jr., the disgraced former congressman who pleaded guilty to misusing more than $750,000 in campaign money, is writing a memoir, two sources familiar with the project told the Chicago Tribune.

A person who has seen drafts of portions of the memoir said Jackson was trying to “clear up his legacy.” “He has nothing else to do right now,” the source said. “He’s desperately trying to change the narrative of his life story.”

Putting pen to paper is nothing new for people in trouble with the law. While former Illinois Gov. Rod Blagojevich was awaiting trial, he wrote “The Governor,” a book in which he blamed his downfall on overzealous prosecutors and political enemies.

Although Jackson is already a published author — he wrote a book of financial advice called “It’s About the Money” with his famous father in 1999, and “A More Perfect Union,” which proposed constitutional amendments dealing with employment, housing, health care and taxes, with an aide in 2001 — he may face an uphill climb to find a find a publisher now, according to Gail Ross, a lawyer and literary agent in Washington.

“To get big money you’d need a publisher who is really, really interested in his story,” she said. “... Maybe someday he’ll write the redemption story, but he can’t write the redemption story until he’s redeemed. Redemption has to be beyond the magnitude of the crimes.”

Jackson, 47, suffers from bipolar disorder and took a medical leave of absence from Congress in June and resigned in November. He will be sentenced June 28 after a seven-year crime spree in which he used the illicit money for a Rolex watch, celebrity memorabilia, furs, a cruise and two stuffed elk heads, among other purchases. He faces between 46 and 57 months in prison and his wife faces one to two years behind bars.

— From wire reports