This month, I’ve been making the case that a wide range of outsiders actually have a better chance of winning the 2028 Democratic nomination than many of the governors & senators considered serious contenders.

Last week, I ranked my #10 through #6 outsiders. Now on to the top 5…

As Democrats belatedly reckon with the wellbeing crisis gripping so many young men – and relatedly, their political erosion with the demographic – many are seeking advice from Scott Galloway.

The 60-year-old entrepreneur/professor turned media star had been warning about this crisis for years & begging leaders to pay attention. Suddenly, everyone is paying attention – to the disaffected men; to whatever Galloway says, which is a lot. He now has a ~$20M/year podcast empire, countless guest spots on other pods, cable news & talk shows, and a highly-anticipated forthcoming book on masculinity,

He is, to be fair, a good listen. Galloway’s rhetorical tours de force weave together unvarnished truths you won’t hear from Dem politicians with data points & anecdotes that’ll stop you in your tracks. (He’s equally likely to mix in a dick joke or tear up while recounting his single mother’s love.)

He aptly describes his niche as the straight white guy who talks about his feelings, though he’s characteristically underselling himself. The self-effacing humor & candor – along with an uncanny ability to generate piercing soundbites – make Galloway one of the most effective messengers in the game right now. 

What really sets him apart from other telegenic outsiders (& frankly most of the field) is that, rather than just trashing Trump & the failed status quo, he actually offers solutions.

“Democrats need to be the party of ideas, not indignation,” he wrote in a March post kicking off a ‘Project 2028’ series on key issues. He sketched out his own ‘grown-up tax bill’ when Ds offered no alternative to Rs’ Big Beautiful. He’s even zoomed in on tangible remedies to counteract the surge of political violence:

Voters won’t agree with Galloway on every issue; he’d find himself to the right of the base on some that could cause trouble, like Israel. But as I’ve argued before, heterodox positions helpfully reinforce non-politician credentials, and people are – if they believe in your character – more forgiving of policy disagreements than we give them credit for.

On Semafor’s Mixed Signals podcast, Galloway recently conceded he was approached about running & was narcissistic enough to consider it for 10 minutes before concluding he doesn’t have the requisite skillset. I’ll buy the anecdote, but dispute the assessment.

In America’s 250-year run as a democracy, a sitting mayor has never won the presidency. Could that streak come to an end in 2028? (The mayor part I mean…)

If SF Mayor Daniel Lurie – the pragmatic centrist Levi’s heir – is not your cup of tea, you may prefer Boston’s Michelle Wu – a tough-as-nails Liz Warren protégé who’s been taking the fight to Trump, among other bullies. I’ve tried to go light on bio in these writeups, but Wu's story is essential to understanding her magic.

Born in Chicago to Taiwanese immigrants, she’d just graduated from Harvard when her mom was struck by late onset schizophrenia. Wu moved back to IL to be her mom’s caretaker & 11-year-old sister’s guardian, then moved them to Boston after getting into Harvard law, eventually taking a job on her professor (Warren)’s 2012 Senate campaign. In 2013 — just 28 & parenting a teenager — Wu won a Boston City Council seat. At 30, she became council president. And in 2021, at 36, she became the first elected Mayor in Boston history who was not a white man.

A soft-spoken introvert by nature, Wu is often underestimated – which tends to end poorly for her foes. Just ask Josh Kraft, son of the billionaire Patriots owner, who launched a buzzy bid to unseat her this year and pumped millions into the race, only to lose the first round by 49 points & withdraw before the general. 

Kraft made missteps, but the events that sealed his fate didn’t involve him at all.

It was Ash Wednesday, and House Rs had called Wu & 3 other mayors to DC to testify in a public flaying on sanctuary cities; she arrived, cross on forehead, 7-week-old baby in arm. For 6 hours, she forcefully defended America’s safest major city & its immigrant community, relishing in her questioners’ inability to land a punch, and the chance to punch back. 

Wu’s steely performance embodied Boston’s notoriously prideful spirit; she returned a hero, burnishing that rep in subsequent Trump showdowns, leading many lefties (like Zohran) to tout her mix of moral clarity & effectiveness as a national model. 

With the base clamoring for a progressive fighter, and moderates crowding the top of the field, there’s a real opening for Wu – and steep hurdles. She’s not flashy & could find attention elusive. Her 2021 campaign was steeped in language & priorities Ds have run away from. She’s struggled to deliver on an overly ambitious agenda & has many fraught issues to navigate ahead. 

Can she really overcome these odds? One thing I’ve learned is, don’t bet against Michelle Wu.

Mark Cuban is not running for president; he’d “rather f**k up health care,” and besides, his “family would disown” him.

He did muse about running in 2016; say in 2017 he’d ‘definitely’ be running if he were single; hire a pollster to assess his viability in 2020; love his swing state town halls in 2024; and it sure doesn’t sound like he’s stopped trying to sell his family. But alas, the door is totally closed.

If he were interested, his personal brand, war chest, attention capital, salesmanship & cross-cultural reach would all be major differentiators working in his favor.

Cuban excels at 3 core competencies of politics: he gets people, cares about people, and connects with people. He leads with values & common sense, and has a Clintonian knack for explaining complex ideas in plain English, at ease in any format or audience. 

He has juice with entire demographics that Dems simply don’t reach, chopping it up on sports, crypto, AI and more with the likes of Theo Von, the Nelk Boys, the All-In bros, Lex Fridman & countless others whose audiences are rich in persuadable voters, but are often dismissed by the left as a (non-existent) monolithic MAGA manoverse. He also hits legacy media & a wide range of sports, health, tech, comedy, & biz platforms.

Cuban’s most underrated asset for 2028 may be his direct-to-consumer online pharmacy, Cost Plus Drugs, which actually is “f**king up” the much-hated health care industry. It’s hard to overstate the value of taking on such potent villains, and delivering for people so tangibly. The  former Shark Tank shark has a killer pitch laying into Big Pharma and its profiteering middlemen, and sketching out a better future.

On other issues, he’d ruffle feathers. I generally think being an affable contrarian is an ideal spot. But there’s a fundamental tension between his everyman populist appeal and his pro-business orientation that could kill him in a Dem primary. He caused headaches for Kamala by torching tough corporate regulators and insisting she wouldn’t tax unrealized gains, and that’s the tip of the iceberg. Other Ds would slam these stances, and he’s wired to hold his ground – points for moxie, but not sure it’d play with the base.

Of course, all of this is moot; Mark Cuban is not running for president, how many times does he have to tell you?

Before I dive into Hasan, here’s a few data points from recent polls. Among Ds:

Now, look at the top Ds in betting markets: Newsom (32%) | AOC (11%) | Pete (8%) | Moore (7%) | Shapiro (6%) | Harris (5%) | Whitmer (5%) | Beshear (5%)

I’d argue not only that AOC is very well-positioned in these atmospherics, but also that there’s plenty of room to the left of her; hunger for more radical departures from the establishment, to which she’s drawn nearer, much to the left’s chagrin.

‘Radical’ is one of many descriptors that’s been bestowed upon 34-year-old Hasan Piker, a leftist streamer who broadcasts 8+ hours of daily news commentary to his 3 million Twitch followers. Others include a “progressive mind in MAGA body” & “himbo gateway drug to the left” – and those were the NYT & NPR headlines!

Piker’s streams attract tens of thousands of viewers. Tune in, and you’ll see why; the dude is captivating – like, Alex Jones levels of intensity, but instead of defaming dead kids & hawking pills, he’s dismantling fascists & feckless Dems. He’s summed up his own appeal neatly: “I communicate the anger that [people] feel in their hearts about the way the system is designed.” 

It sounds simple, but few could pull this off.

Indeed, nobody else is doing this – Hasan is a 1-man bro-gressive antidote to an entire right-wing ecosystem for Gen Z men. He’s a freakish political athlete & intellectual heavyweight, alternating seamlessly between Chomsky & meme-brained internet references (both of which go over my head) as he sells you on his subversive worldview. 

Speaking of which, I should mention that he’s a self-avowed Marxist, a fierce anti-Zionist accused of veering into antisemitism, and once said America deserved 9/11, among many other inflammatory comments.

But the reality is, he’d love to have a protracted debate about his staunch Israel opposition and support for free college & Medicare For All. Indeed, he’s been begging top Dems to go big on a couple signature policies so people know what they stand for.

With the right eager to cast him as Dems’ avatar, Dems eager to denounce incendiary voices on the left, and the left eager for iconoclasts, Piker & his radical agenda would surely be thrust to center stage for that debate. What happens if he wins it?

It’s strange to say about a guy who hosts a late-night comedy show (or so it seemed when I started writing this, before late-night hosts became the face of the resistance), but Jon Stewart has been an enduring moral compass for a generation of progressives – the primary conduit through which many got their trusted news, and the rare public figure who’s consistently sought to hold power to account, rather than accumulate it.

Part of Stewart’s uniqueness is the breadth of his appeal; nobody else in the party is so evenly admired by its leftist & centrist wings. In part, that’s cuz he's not of the party at all, but an authentic outsider & equal-opportunity incinerator of Beltway bullshit; a fighter for workers & a corporate antagonist; a values-first communicator, who leverages his platform & charisma to give voice to the voiceless.

Last month, the comedian got a boost from two fellow media luminaries with very different audiences –– Breakfast Club host Charlamagne Tha God, who named Jon as his preferred nominee, and Zeteo’s Mehdi Hasan, who made a convincing progressive case for Stewart 2028. How many megamillionaire, Hollywood-looking, wine mom-approved, 60something Jews are getting that stamp of approval? 

Stewart surely wouldn’t enjoy such uniform & broad-based support for the duration of the primary process. But that’s okay. In fact, if there’s one thing I’m certain of, it’s that the ultimate nominee will be someone who’s clear-eyed, strong-willed, & comfortable enough in their own skin to take stands that piss off one constituency or the other, and not buckle when the yelling starts.

All of which brings me back to February 2024, when Jon Stewart returned to The Daily Show host chair after a 9-year hiatus… 

Many libs were incensed when Stewart, in his first show back, called out Joe Biden’s obvious cognitive decline, halfhearted objections to Bibi’s escalating war crimes, and the decision to skip a softball Super Bowl interview that would’ve reached 100M+ viewers. Safe to say: those takes aged well, and Dems would be better served by a truth-teller with Stewart’s disdain for partisan charades than more dutiful partisans with disdain for the voters.

Jon Stewart seems to be aging pretty well, too.

Thanks for reading! The next one will be shorter, I promise.