When Barack and Michelle Obama were married in Chicago two decades ago, Santita Jackson, a daughter of the Rev. Jesse L. Jackson, sang at their wedding. When Mr. Obama ran for his first national office, he made sure he was not stepping on the ambitions of her brother, Jesse L. Jackson Jr., who later became a co-chairman of his 2008 presidential campaign.
Now the younger Mr. 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 Mr. Jackson and Mr. 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, Mr. Jackson was seen as a far more promising figure than his friend Mr. Obama — one the heir to a legend, the other an outsider seeking to surpass the father he barely knew. If Mr. Jackson had decided to run for the United States Senate in 2004, Mr. Obama most likely would not be president. That year and again in 2008, Mr. Obama, seeking to bolster his credibility with African-Americans, enlisted the younger Mr. 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. Mr. Obama, who saw the Jacksons’ problems up close, increasingly kept his distance from both men. Now, the Obama administration’s Department of Justice is poised to send the younger Mr. Jackson — who came under investigation after he pursued but failed to obtain Mr. Obama’s old Senate seat — to prison.
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