Gov. JB Pritzker and former Chicago Mayor Rahm Emanuel may be gearing up for a 2028 White House bid. If both run, they would be jumping into a contest that will be congested and fraught with peril.
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They would also be very, very, long, long shots.
According to the Kalshi prediction market, which assesses the odds on everything in the world, both candidates’ chances to grab the 2028 Democratic presidential nomination are at 2% or less.
Long shots, indeed, but if they can get traction, the pair brings a keen contrast in style, politics and resources.
Pritzker is a billionaire with a near-endless stream of cash to self-fund a campaign, and he is not shy about funding allies to stand with him in a 2028 run.
Note just his recent largesse: Pritzker gave $1.56 million to state and local races in Illinois from Jan. 13, 2025, to March 17, 2026, according to an analysis by the Illinois Policy Institute. And the governor contributed $12.3 million to national, out-of-state political committees from April 2025 through March 2026.
There’s plenty more where that came from.
Emanuel’s closest ally is his brother Ari, the Hollywood mega agent and CEO of the WME Group, a massive entertainment and media agency. Ari Emanuel’s clients comprise a top-tier list of boldface names and influencers. His scores of connections offer Rahm a gold-plated megaphone.
In style, Emanuel is abrasive, combative, arrogant, yet highly effectual. He gets stuff done, but he leaves a bad taste in your mouth while he’s ramming his ideas down your throat. Emanuel is the kind of guy you want on your team, but he needs to be reined in from time to time.
Years ago, my husband and I attended a small dinner with Emanuel. All he did was talk about himself. All night.
Pritzker, on the other hand, is one of the most socially adept politicians I have covered. He listens. He has a sense of humor that comes through unself-consciously. Back during his first gubernatorial run, we attended a get-to-know-you-dinner with Pritzker and his wife, MK, at the fabled Yoshi’s Cafe.
As a reporter, there was no way I could let a candidate pick up my check. So as the dinner was winding down, I tugged on hubby’s sleeve and whispered, “Pay the bill.”
When it was time to leave, Pritzker asked for the check. My other half turned slowly to Pritzker and said, “Don’t worry about it. It’s done.”
My husband then proceeded to look the billionaire straight in the eye and declare, “Now, I own you!” Pritzker broke up laughing.
A successful politician needs a sense of humor. Emanuel? Not.
The political philosophies of Pritzker and Emanuel are as divergent as their styles.
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Democrats have been crippled by a misguided and delusional left wing of the party, Emanuel argues as he travels around the country on his presidential exploration journey. His case is that getting back to the center is where Democrats belong.
As Politico noted earlier this year, Emanuel is fond of saying that he is “done with the discussion of locker rooms, I am done with the discussion of bathrooms — and we better start having a conversation about the classroom.”
He is highly critical of the Democrats’ rhetoric around issues like transgender rights, arguing his party should focus on issues like education reform. In many ways, Emanuel’s critique of intraparty battles is bang-on. He is deploying presidential talk to steer Democrats back to the center, where most voters reside. President Donald Trump is trying hard to polarize the Democrats and force them leftward. That’s a place where they will never capture majorities in the U.S. Senate and House.
Pritzker is a bird of a different feather. His politics are business friendly, but on social issues he leans left. Not as left, mind you, as U.S. Sen. Bernie Sanders, U.S. Rep. Alexandria Ocasio-Cortez or New York City Mayor Zohran Mamdani, but Pritzker is far to the left of Emanuel.
Pritzker’s disgust with Trump is a vocal weapon that he wears prominently on his sleeve.
In the COVID era, the governor was forced to beg Trump, mostly in vain, in a desperate quest to obtain lifesaving masks and ventilators, leaving him deeply skeptical of the president’s fitness for office. Pritzker delivers regular, stinging broadsides against Trump, earning him national accolades from Democrats of all stripes.
There is one characteristic Pritzker and Emanuel share as they ponder White House bids: They are Jewish.
The Jewish voters I talk to are unnerved by that. They worry that the prospect of a Jewish president might renew and replenish the flames of antisemitism. It’s the-nail-that-stands-up-gets-hammered syndrome.
One thing I know for sure. In these times, anyone embarking on a serious campaign for the White House must have a mountain of chutzpah.
Laura Washington is a political commentator and longtime Chicago journalist. Her columns appear in the Tribune each Wednesday. Write to her at [email protected].
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