In the golden haze of post-2008 euphoria, the Democratic Party crowned a new high priesthood: the Obama campaign alumni. They were young, sharp, and seemingly unstoppable, riding Barack Obama’s meteoric rise to historic victories. But now, as the party surveys the wreckage of three successive defeats at the hands of Donald J. Trump, Democratic insiders are starting to say aloud what some have whispered for years: Obama’s team was never as good as their mythology suggested—and they may have hollowed out the Democratic Party in the process.
The secret history of the shadow campaign that saved the 2020 electionhttps://t.co/G82mFbIeGA
— TIME (@TIME) February 6, 2021
You don’t need to be a historian to recognize the truth: Obama was a political unicorn, a candidate whose appeal transcended traditional categories. His charisma, poise, and rhetorical fluency were sui generis—so much so that his success was personal, not institutional. The consultants around him were lifted by his wave, but never able to reproduce that magic for anyone else.
They certainly tried. Over the past decade, the Obama alumni network embedded itself across every strategic rung of Democratic politics, from convention programming to campaign strategy to party fundraising. And what has it yielded?
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The collapse of state Democratic parties during Obama’s presidency.
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A Clinton 2016 campaign that flamed out against a political amateur.
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A Harris 2024 disaster, culminating in a devastating loss to Trump.
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A Biden presidency propped up by Obama-era retreads, and now viewed by many in both parties as a historic failure.
Now, a growing chorus of Democrats is finally asking the obvious question: Are we hiring “winners” or just resume padders?
Campaign veteran Chris Kofinis nailed the sentiment:
“I’m sorry — I don’t want a surgeon who keeps killing patients.”
There’s a dangerous delusion in both political parties that victory begets operational genius. But Obama’s win didn’t mean his team could repeat it—just like Michael Jordan’s greatness didn’t make his coaches immortal. Obama’s victories were, fundamentally, about Obama.
And that reality is now crashing into the careers of people like David Plouffe, Jim Messina, and Stephanie Cutter, who’ve been handed big campaign roles for lackluster candidates like Kamala Harris and Joe Biden—and delivered nothing but losses.
MSNBC – 5/28/2025 – Obama world loses its shine in a changing hurting Democratic party pic.twitter.com/0miwQAiybV
— CaseStudyQB (@CaseStudyQB) May 28, 2025
The Harris 2024 collapse might be the breaking point. Plouffe, once hailed as the brains behind Obama ’08, is now tagged with managing a campaign that couldn’t convince Americans to vote for a woman who has spent four years as the human embodiment of awkward. Messina, wisely, took a pass on helping Harris, reportedly warned off by Democratic megadonors who saw the writing on the wall: Hitch your wagon to Kamala, and you go down with her.
When even Obama’s inner circle starts dodging opportunities to “serve”, you know the mystique is fading.
So where does the party go from here? Some Democrats seem eager to replace the old guard with a new generation of hyper-progressive activists, betting on a rainbow coalition of the Twitter-verified and TikTok-mobilized. But let’s not kid ourselves—leather-clad, blue-haired “community organizers” knocking on suburban doors won’t win back middle America.
Obama’s team, for all their faults, could at least talk to donors, corporate media, and the DC elite. The next wave? It’s unclear whether they even want to talk to the working-class voters who once formed the bedrock of the party.
Democrats are spending $20 million studying how to talk to men, like a National Geographic journalist visiting animals in their native habitat. They just can’t figure out why the working-class voter has abandoned the party that hates them. Oh, and the SPLC finally put TPUSA on… pic.twitter.com/SmVuyFgL8G
— Charlie Kirk (@charliekirk11) May 28, 2025
Let’s also remember: Obama picked Biden, setting the stage for the 2020 basement campaign and its dark-money-driven rule changes. He picked Hillary Clinton, teeing up a historically unpopular candidate to lose to Trump in 2016. He disengaged from party-building, instead leaving Democrats structurally hollowed out at the state level.
And now, every electoral cycle since he left office has involved Democrats trying to relive 2008’s magic—with diminishing returns.