Former Chicago Mayor Sets Sights on the White House

June 15, 2026

Buyer beware

There he was. It was Rahm Emmanuel on national television attending a New York Knicks–San Antonio Spurs championship series game. The former Chicago mayor was sitting in floor seats of which the price ranges between $75,000–$135,000. Who knew he was a Knicks fan? It's convenient to have a super-agent brother who also happens to be securing you an interview on practically every mainstream cable show and podcast, lecturing us about how the Democratic Party has lost its way while presenting himself as its moderate voice of reason.

I had been reluctant to write about Rahm, who in presidential preference polling is barely registering. Illinois’ other presidential hopeful — Governor JB Pritzker — is polling at just two percent. One gets the feeling the country is tiring from Illinois expatriates running the country. Not our best export. However, Emanuel took time out of his Don Quixote-like quest for the White House to stop in Chicago to meet with my biggest supporter to urge them not to support me making another run for mayor or a run for Chicago School Board president.

Emanuel has always had an unhealthy obsession with me ever since he was marginalized when President Bill Clinton would come to town to praise the school system when I served as CEO of the Chicago Public Schools and Gary Chico served as president of the School Board. Or maybe it was because I had the temerity to challenge him when he was contemplating a third term, upsetting a carefully orchestrated plan to keep White and Hispanic challengers out of the primary — other than former Police Superintendent Gary McCarthy, who Emanuel shamelessly scapegoated for the Laquan McDonald shooting.

Now in search of his next gig, Emanuel is certainly personally well positioned financially. Emanuel is a poster child for politicians drinking from the special-interest trough. Former Governor Bruce Rauner, at the request of President Clinton, made Emanuel a wealthy man during his short term at Wasserstein Perella in the late 1990s, collecting roughly $16.2 million in a half-billion-dollar acquisition for Rauner’s firm, GTCR. Between the Mayor’s Office and being Japanese ambassador, he picked another $13 million from private-sector ventures and consulting.

Now, Emanuel is actively seeking a place to land, but has little to offer. Unwilling to step away from the political sphere and with Trump in office, Emanuel finds himself at a juncture at which it is more difficult to receive appointments to premium boards. Elsewhere, Emanuel can neither act as a broker to grant access to the powerful nor play a role in securing government deals for the influential. Rahm wants to run for president.

A man seeking a purpose, Emanuel has reemerged and is now showing up at Trump-bashing press conferences, hustling interviews at the Economic Club, or relying on his Hollywood-agent brother. Opining on Bill Maher’s show, Emanuel spoke of how the Democratic Party lost its way after remaining silent during the backroom maneuvering that saw Kamala Harris replace Joe Biden on the presidential ticket, and how the Democrats self-destructed with its embrace of identity politics. 

One thing is clear: Emanuel isn’t the answer to what ails the Democratic Party, let alone the presidency. Many of the problems the party faces today — including a number of important issues like immigration that the country has struggled with — can be attributed to his time in leadership in Congress. It should also not be lost on voters that Emanuel’s two terms as mayor were disastrous and largely responsible for the emergence of the CTU and the far-left leadership that now dominates Chicago.

As Emanuel was offering guidance to the Democratic Party after the fact and lecturing Maher and his fellow guest, Fareed Zakaria, on what competent municipal governance entails, we are reminded of Emanuel’s tenure — a disaster in my opinion — in elected office. In his undistinguished career as a member of the U.S. House, Emanuel served as then-Speaker Nancy Pelosi’s top political assassin. Of note was Rahm’s direct role in killing the immigration reform compromise, which was widely blamed by immigration advocates for the failure of the House to pass two comprehensive reform measures.

This was no small matter, since Democrats controlled both houses of Congress from 2007 to 2009. They could have passed immigration reform with the support of a sympathetic Republican president named George W. Bush. And yet, as was very well reported at the time, Emanuel decided immigration was not worth the trouble. He once referred to it as the “third rail” of American politics.

Emanuel even tried to get support among his Democratic colleagues for a dreadful bill sponsored by then-Rep. Jim Sensenbrenner (R-Wis.), that sought to make into a felony the simple act of being in the United States without the proper documents. This way, Democrats would be inoculated at re-election time from the accusation of being “pro-amnesty.”

Emanuel was just getting warmed up. When he left Congress to become President Barack Obama’s chief of staff, Emanuel helped put comprehensive immigration reform on the back burner, fortified the border with more fencing and border patrol agents, and racked up a record number of deportations. A Luca Brasi figure — following his unceremonious dismissal from the Obama White House, Emanuel served two terms as Chicago mayor, a period which was riven with poor judgment and ended in disgrace.

Despite his poor record in office, there Emanuel was explaining to Bill Maher Mayor Brandon Johnson’s approval rating had plummeted because he had failed to focus on the basics — strong finances, quality schools, safe streets. In Rahm’s two terms, “strong finances” meant furthering Chicago’s fiscal insanity by saddling residents with the largest increases to city property and school-district property taxes on record.

On education, “strong schools” meant returning to social promotion as the district bragged about historic graduation rates despite abysmal test scores. He bungled school closures, then caved to the CTU, denying public charter schools the opportunity to use any of the closed school buildings. Emanuel’s desire for a nasty feud with the CTU — slighting educators in public — incited a radicalization of the union and sired the unruly, unhinged CORE caucus that has since inflicted incalculable damage to the schools and the city.

Who can forget his “teachers received raises while students got the shaft" statement that became a front page headline as he moved to violate the teacher’s contract by having his appointed school board rescind a four percent teachers' pay raise. Or his attempt to further hobble the union’s already limited collective bargaining rights by lobbying for a state law raising the threshold for a strike vote to 75 percent and limiting negotiations strictly to salary, rather than working conditions. Emanuel then insulted and offended every teacher in the system, thereby helping solidify militant CORE leadership over the union.

Under Emanuel, “safe streets” meant stripping CPD of over 2,000 police positions, including the elimination of almost 400 detective positions. Crime dramatically surged, forcing him to restore virtually all those positions late in his second term as he prepared for reelection to bring crime down. In what will perpetually dishonor his tenure as mayor, Emanuel took part in a coverup of the shooting death of an armed teen and then conveniently used the CPD then-superintendent of police, Garry McCarthy, and the entire CPD as a foil to ensure his political survival.

Even on the infamous parking-meter deal — which many estimates say will have cost the city billions — Emanuel publicly called the 75-year lease of the city’s 36,000 meters initiated by his predecessor, Richard M. Daley, a “bad deal.” Yet his administration’s actions in court and subsequent renegotiation in 2013 effectively locked the deal in place. The Emanuel administration teamed with Chicago Parking Meters LLC (CPM) to fight a 2009 lawsuit filed by attorney Clint Krislov that aimed to declare the deal illegal, arguing the city was benefiting from the arrangement.

Now Rahm wants to be president, trying to carve out a middle-of-the-road alternative to a plethora of potential candidates on the progressive left by gently chastising gender ideology and identity politics while flipping on his long support of Israel to avoid a complete break. Emanuel sat meekly silent for a decade while the party inflicted extraordinary harms on vulnerable children until the mania at last exacted an electoral price and created a sliver of an opening to break with the mandatory absurdities that still hold every other party member in its grip — showing the Orwellian power of this movement.

Rahm did not believe men could become women when he used taxpayer funds to transition children a decade ago. He was just doing what he was told, and would never have admitted his disbelief if Kamala Harris had been elected president. Remember that Emanuel was the first mayor in America, 10 years ago, to use taxpayer dollars to pay for sex-change surgeries. But it is the flip-flop on Israel that is most disingenuous.

There is no better example of Emanuel’s political opportunism than his shift on Israel, calling for an end to U.S. taxpayer-funded military aid to the country. While a long-time supporter of Israel, Emanuel now argues, as a wealthy nation, Israel should pay for its own defense. Emanuel tries to cover his shift on Israel by making that shift all about Israeli President Benjamin Netanyahu — actually claiming Jewish settlements are the primary source of the current conflict.

Emanuel noted his position reflects a changing landscape within the Democratic Party, where both progressive and, increasingly, moderate voters are critical of Israel’s actions. In a departure from his previously hawkish stance, Emanuel stated “the United States should never spill any blood for Israel’s security.” This is all about his pandering to the far left on Israel, hoping they will be distracted from his more moderate views on other issues. It has nothing to do with core beliefs but is pure political calculation.

Decades ago he “swapped” Chicago politics for the national stage when he helped lead the Obama White House. Then he “swapped back” to Chicago — and now he is trying to re-enter national politics once again. Like Newsom, the only thing consistent about Emanuel is his inconsistency. In his efforts to separate himself from the progressive pact, he is now a critic of gender ideology and identity politics, which he had previously been neutral on or indirectly embraced — but only when it comes to bathrooms. As evidenced by his recent “betrayal” of Israel, he backtracks and flip-flops wherever possible.

Now he is trying to brand himself as a moderate — we shouldn’t be fooled.

Rahm Emanuel, Pointing, With Chicago Flag in Background by Daniel X. O'Neil, CC BY 2.0

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