With the midterms and 2028 looming like a cloud of uncertainty, the Democrats have called on their most esteemed persuader, Barack Hussein Obama. Like Whac-A-Mole, the man who should be retired keeps popping up everywhere, doling out pointers on how redistricting could deliver a Democrat victory from the jaws of defeat.
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Why Obama? Because this is a man whose favorite topic is that anyone or anything threatening Democrat control of America is the antithesis of his own stilted vision of democracy. Remember that Obama called for “fundamental transformation.” But how to get there is not set in stone, because Obama is willing to be flexible if that flexibility ensures Democrats defeat those who oppose his transformational change.
Obama has spent years condemning partisan gerrymandering as something that distorts democracy — or rather, his distorted definition of “democracy.” Lest we forget, partisan redistricting can ensure that the same statewide electorate produces a of congressional seats depending on where the district lines are drawn.
In 2016, while discussing partisan redistricting, Obama said, “In America, politicians should not pick their voters; voters should pick their politicians.” He immediately added that this principle should apply “across the nation, not just in a select few states. It should be done everywhere.”
In other words, on the surface, Obama wasn’t merely condemning a party that benefits from redistricting; he was condemning whichever party is in power for drawing districts to gain a partisan advantage, which is not illegal. But trust me: Obama is just fine with using redistricting if it steers an election left.
Don’t you love how good ol’ Obama always includes his party in the condemnation, appears evenhanded, and then pivots to condemnation and justification? It’s classic Obama.
Less than a decade later, after Texas did what Obama said he disapproved of, Obama-style sibilance is whistling a different tune by recommending a similar tactic.
After stressing his bipartisan creed and advocating electoral honesty, who would have thought that, after criticizing partisan gerrymandering and accusing politicians of “choosing voters,” Obama would respond to Republican mid-decade gerrymandering in Texas by encouraging Democrats to engage in redistricting?
In 2025–26, Obama promoted and actively supported Democrat counter-redistricting similar to the Republican redistricting he once opposed, because he now says it “levels the playing field,” a slogan used by Marxist socialists who want to “share the wealth.” This time it’s political wealth, as the left, led by Obama, is attempting to redraw district boundaries to further the lagging fundamental transformation of America.
Adopting Republican policy worked when, in response to Texas’s mid-decade gerrymander, California adopted what Democrats had criticized. That redistricting effort helped California pass Proposition 50. Prop. 50 was a direct response to “Texas’ mid-decade partisan congressional redistricting” and was passed just in time for 2026.
Meanwhile, back on Martha’s Vineyard, Obama-era attorney general Eric Holder is still spending time with the former president. Holder has publicly acknowledged that the current redistricting approach he and Obama are now pushing “kind of goes against what we talked about” before. Why are these two advocating for something they once criticized? Because both left-wing activists believe that changing direction and embracing what they now call anti-democratic is necessary to advance Obama’s tainted definition of democracy.
If Obama et al. now believe it’s beneficial to support redistricting to counter Republicans, the question for the rest of us, who’ve been regularly chided by the former president about how democracy works, is this: “Has the practice you and your cohorts repeatedly described as undemocratic become acceptable simply because your opponents have the advantage in the midterms?”
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What other tactics is Obama willing to adopt as his own if doing so ensures political expediency? On principle, Obama seems surprisingly malleable when political circumstances shift, as he did on super-PACs, executive privilege, and raising the debt ceiling.
This isn’t Obama humbly acquiescing to the brilliance of Republican political strategy. It’s a haughty, self-impressed man likely adopting some of what Saul Alinsky taught community activists in Chicago — namely, advising street-level organizers to “make the enemy live up to their own book of rules.”
Alinsky was all for holding his adversaries rigorously to principle while retaining tactical flexibility for himself. So changing his mind about redistricting might be Barack Obama’s way of finding an avenue to gain power by using what he criticized — adapting his tactics to the circumstances, Alinsky-style.
That’s why, in August 2025, Obama reportedly defended California’s response to Texas at a Martha’s Vineyard fundraiser, saying Texas was acting at the direction of a partisan White House, and then praised Gavin Newsom’s approach to countering the effort.
So here we are: It’s the end of summer in 2026, a few months before the midterms. The old standby Obama either has been called into action or has volunteered to weigh in on how to adopt Republican techniques. Judging from his Slim Shady antics, one shouldn’t be surprised if we find out that disagreeing with redistricting and then implementing it in retaliation against Republican methods in Texas wasn’t part of the Democrat plan from the beginning. Disagree, appear to take the high ground, and then gaslight Republicans by saying you were forced to do what you disagreed with out of fairness and necessity.
This is a modern-day Scipio Africanus — Obama drawing up battle plans to defeat Hannibal Republicanus by turning his adversary’s strengths and tactics against him.
As the troops rally, Commander Obama was scheduled on August 31 to offer his professorial advice at a National Democratic Redistricting Committee fundraiser on Martha’s Vineyard — an event, ironically, hosted by a man closely associated with the Obama-era “Fast and Furious” scandal.
The fundraiser was held in a tony Massachusetts enclave, home to left-leaning voters more than willing to vote to ensure that all of us are subjected to things they’re rarely subjected to themselves.
Although this is all speculation, based on the contents of former transcripts on a similar topic, if I were a betting woman, I would imagine the speech included the usual threat-to-democracy twaddle, vilification of Trump, opposition to ICE, and warnings to those sipping martinis and munching on fig-and-prosciutto hors d’oeuvres about the realities of Republican voter suppression.
All this mystery raises questions about what kind of advice Obama actually gave political activists beyond the suggestion and basic premises of redistricting. Did he up the ante? Raise the stakes? Throw caution to the wind?
Whether Obama advised his rapt audience on how to influence or deter support for the SAVE Act or bantered about voter ID being racially oppressive, no one knows for sure. But we do know that, unlike his 2016 comments, the verbatim transcript of Obama’s unofficial “fighting fire with fire” event has not been published or released by major news outlets to date.
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Image: Ari Levinson via Wikimedia Commons, CC BY-SA 3.0 (cropped).