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Jesse Jackson, Complicated Man – The American Conservative

Wayne Park
Last updated: February 19, 2026 7:05 am
Last updated: February 19, 2026 6 Min Read
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Jesse Jackson, Complicated Man – The American Conservative
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The veteran conservative journalist Tom Bethell coined the phrase “strange new respect” to describe liberal media adulation of a formerly conservative—or in today’s parlance, right-coded—figure who shifts leftward.

What then describes the somewhat more than grudging MAGA admiration for Jesse Jackson, the civil rights activist and two-time Democratic presidential candidate who died Tuesday? 

President Donald Trump had a long history with Jackson before entering politics and becoming a right-coded figure himself. Trump’s Truth Social post on Jackson’s death was surprisingly laudatory, even warm, and slightly more personal than his video tribute to conservative talk-radio icon Rush Limbaugh, who died five years earlier on the same date.

The Trump nominee Jeremy Carl shared a 1988 Jackson for president commercial, calling it “one of the best campaign ads I’ve ever seen.” Vice President J.D. Vance reposted Carl, saying he had a “close family member” who had only voted in two presidential primaries in her whole life: once for Jackson in 1988 and then for Trump in 2016.

A Jackson-Trump voter would at first glance seem like a stranger political specimen than the Obama-Trump voters who helped swing the 2016 election.

But perhaps not. Jackson was a populist, even if he was a man of the left. He was in his own day and way trying to forge the multiracial working-class coalition that many populists on the right envision now. He was defeated for the Democratic nomination by the most boring liberal technocrat imaginable, with predictable general-election results. 

Nevertheless, after the evangelist Billy Graham delivered invocations at both the Republican and Democratic conventions in 1988, he recalled the Democrats being more enthusiastically prayerful. This was largely due to the presence of a large group of Jackson delegates, many of whom were black Christians. 

The late conservative humorist P.J. O’Rourke memorably reacted to Jackson’s powerful convention speech by describing the preacher-turned-pol as the “only living American politician with a mastery of classical rhetoric. Assonance, alliteration, litotes, pleonasm, parallelism, exclamation, climax and epigram—to listen to Jesse Jackson is to hear everything mankind has learned about public speaking since Demosthenes.”

“Thus Jackson,” O’Rourke concluded, “the advocate for people who believe themselves to be excluded from Western culture, was the only 1988 presidential candidate to exhibit any of it.” 

Demosthenes and “Hey-hey, ho-ho, Western civ has got to go” from the same political leader. 

The Jackson campaign ad Carl highlighted, with its outreach to working-class whites, could have been released by Trump or Pat Buchanan. When Buchanan and Jackson were both commentators at CNN together, they would sometimes agree more than they would disagree about the plight of blue-collar workers.

Jackson once needled Buchanan on school prayer, a cause for which the Democrat had some sympathy, saying some schools in the South once had “maximum prayer” and “maximum segregation.” Buchanan shot back that segregation was wrong but prayer in school was right. 

Jackson was far from perfect. He vacillated between working with Republicans when useful on policy and calling them racists when politically expedient. Like many ambitious Democrats in the 1980s, he abandoned his pro-life defense of the unborn in pursuit of power. Unlike Al Gore, Ted Kennedy, Dick Gephardt or Dick Durbin, however, Jackson was a Christian minister. 

The former aide to Martin Luther King Jr. in many ways personified the civil rights movement’s decline from the preeminent human rights cause of 20th-century America to a network of aging political organizations defined by extreme partisanship, racial quotas, and DEI extortionism, even if he continued to do some good work intermingled with the grifterism. 

Jackson gave Bill Clinton the opportunity for his Sister Souljah moment by not sufficiently policing anti-white racism in his own movement. Along with the shameful, antisemitic “Hymietown” quote and his increasing reluctance to defend black American workers’ economic interests from uncontrolled mass immigration, such tendencies fractured the Rainbow Coalition as a concept for a multiracial working-class political movement, if not as an advocacy organization renting office space from Trump.

While Jackson tearfully celebrated Barack Obama’s 2008 election as the country’s first black president, likely viewing it as a culmination of his life’s work, the two famously had a somewhat more complicated relationship. While Jackson has been even more critical of Trump over the past decade, it would hardly be surprising if the two of them occasionally commiserated about their shared frustrations with Obama.

For all his faults, Jackson was a throwback to a more interesting and complex time in American politics—and perhaps an early predictor of a new one to come.



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