Going Out Like Stan Chera

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Published July 28, 2026

"Going Out Like Stan Chera" is a catchphrase reportedly uttered by Donald Trump during his October 2020 bout with COVID-19, in which he repeatedly asked aides if he was "going out like Stan Chera," referring to his friend, New York real estate mogul Stanley Chera, who had died from the virus earlier that year1. The quote quickly became a darkly comedic Twitter catchphrase used to describe anything that seems to be dying or failing2.

Overview

The phrase comes from a moment of private panic during one of the most scrutinized illnesses in modern political history. After testing positive for COVID-19 in early October 2020, Trump reportedly turned to aides and asked, repeatedly, whether he was "going out like Stan Chera"2. The phrasing struck people as quintessentially Trumpian: the casual use of "going out" instead of "dying," the fixation on a single personal connection rather than the hundreds of thousands already dead from the pandemic1. Stan Chera was a New York real estate mogul and close friend of Trump's who had contracted COVID-19, fallen into a coma, and died in April 20201.

Origin & Background

Platform
Vanity Fair (reporting), Twitter (viral spread)
Key People
Donald Trump, Gabriel Sherman
Date
2020

On October 3, 2020, Vanity Fair columnist Gabriel Sherman reported that while the White House publicly projected optimism about Donald and Melania Trump's COVID-19 diagnoses, the situation behind closed doors was more "dire"2. Sherman's reporting revealed that Trump had been asking those around him if he was "going out like Stan Chera," a real estate developer and longtime friend who had died from the coronavirus roughly six months earlier2.

The New York Times later published a detailed profile of Chera, providing context for why Trump's mind went to this particular person1. Chera was a quietly powerful figure in Manhattan real estate, the head of Crown Acquisitions, who had built his empire through retail repositioning and strategic partnerships within the Syrian-Jewish business community1. He and Trump met in the 1980s, and Chera became a fervent supporter of Trump's political career, hosting fundraisers and attending White House dinner parties1. Steven Witkoff, a mutual friend, described these visits as Trump's way of decompressing with "real estate people"1.

The Times profile noted the irony of Trump's fear: "Trump may have been sick, but he never had a chance of going out like Stan Chera"1. Where Chera was private and strategic, Trump was public and chaotic. Their approaches to wealth and power were almost diametrically opposed1.

How It Spread

The quote landed on social media almost immediately after Sherman's report. On October 3, 2020, Twitter user @joolsd posted that the line would make a great moment in a Trump biopic, picking up over 70 likes2. That same day, @mrmikeyreid joked they'd use the phrase whenever their tweets were bombing, gaining over 90 likes2.

The catchphrase stuck around on Twitter well past the initial news cycle. On August 25, 2021, @Chinchillazllla tweeted that they used the phrase anytime they started feeling COVID symptoms, as a kind of dark self-comfort, earning over 300 likes2. On March 22, 2022, @MandelaFace combined it with another infamous political meme when Hillary Clinton caught COVID, tweeting "Pokémon Go out like Stan Chera," a mashup referencing Clinton's widely mocked 2016 "Pokémon GO to the polls" line2. The tweet picked up over 70 likes2.

The meme found its niche as a flexible expression of doom, applied not just to illness but to anything perceived as circling the drain: failing projects, tanking stocks, bad tweets, dying trends2.

How to Use This Meme

The phrase works as a punchline for any situation where something (or someone) appears to be on its way out. Common uses include:

- Describing personal setbacks: "My GPA is going out like Stan Chera" - Commenting on failing institutions or brands - Self-deprecating humor about one's own declining relevance or health - Mashing up with other political catchphrases for layered jokes, like the "Pokémon Go out like Stan Chera" format2

The humor typically comes from the absurd grandiosity of the original context applied to something mundane.

Cultural Impact

The quote offered a rare window into Trump's psychology during a moment of genuine vulnerability, which the New York Times explored in depth1. The magazine piece framed Chera as Trump's "foil," a man who accumulated power quietly while Trump did everything loudly1. The phrase's viral life said something about how the internet processes political figures: even Trump's private fears got workshopped into comedy material within hours.

Chera's own legacy, largely unknown outside New York real estate circles before the quote went viral, briefly entered public consciousness. His career spanned decades of Manhattan deal-making, from the former Marcos properties to Fifth Avenue retail flagships like Uniqlo and Forever 211. His involvement with Jared Kushner's troubled 666 Fifth Avenue purchase also drew renewed attention1.

Fun Facts

Chera got his start in real estate using income from his family's department stores to buy retail buildings in Downtown Brooklyn in the late 1970s1.

Crown Acquisitions reportedly walked away with $25-50 million in profits from the 666 Fifth Avenue retail deal, while Kushner's company bled money on the tower itself1.

The phrase "going out" instead of "dying" was noted by multiple commentators as a distinctly Trump-like linguistic choice1.

Chera hosted a fundraiser for Trump at his home in the summer of 20161.

Frequently Asked Questions