On a crisp Saturday in October 2025, the heart of Washington, D.C. pulsed with the chants and banners of the "No Kings" rally, a protest aimed squarely at the Trump administration and its policies. Among the crowd, one attendee drew particular attention: George Conway, the former Republican attorney and co-founder of the anti-Trump Lincoln Project. Conway, a figure well-known for his outspoken criticism of former President Donald Trump, made a bold statement by wearing a black T-shirt emblazoned with the words, “I am Antifa.”
According to Daily Caller, Conway’s choice of attire was no accident. He was photographed at the rally by a reporter from the Daily Caller News Foundation (DCNF), and the image quickly made its way across social media platforms. Conway himself shared the photo on Bluesky, a left-leaning social network, thanking the photographer and encouraging others to tag him and share their own content from the event. The shirt, and Conway’s presence, became a lightning rod for discussion online, with critics and supporters alike weighing in on what it meant for a prominent conservative-turned-Trump-critic to so publicly align himself with Antifa, a group President Trump had recently labeled as a domestic terrorist organization.
The “No Kings” rally was not an isolated event. It was one of numerous protests held nationwide on October 18, all united in their opposition to what organizers described as the Trump administration’s authoritarian tendencies. The official website for the event emphasized a commitment to nonviolent action, framing the demonstrations as peaceful resistance against perceived overreach and threats to democracy. Yet, as MEAWW reported, the protest’s message of nonviolence was complicated by the actions and rhetoric of some radical leftist groups. Anonymous blogs linked to the international anarchist collective CrimethInc encouraged more aggressive tactics, urging supporters to engage in “anti-authoritarian” uprisings reminiscent of the 2020 Black Lives Matter protests. CrimethInc specifically advocated for “direct action planning,” a strategy they described as mobilizing people to create public disruption—even at the risk of arrest.
These calls for radical action were reflected in some of the imagery and slogans seen at the rally. As documented by the DCNF, signs bearing the numbers “8647” were visible—a sequence interpreted by Cassell’s Dictionary of Slang as meaning “kill” or “murder.” One protester was even seen carrying a poster depicting what appeared to be a guillotine, an image that evoked the violent upheavals of past revolutions. While the majority of demonstrators maintained a peaceful stance, such symbols fueled debate about the boundaries between protest and provocation.
Conway, meanwhile, could not be reached for direct comment on his motivations that day. However, his recent public statements offer some insight. Earlier in 2025, Conway became emotional during an appearance on 'The Bulwark Podcast,' where he accused Trump of posing a grave threat to “democracy” and the “rule of law.” He was quoted as saying, “What we have here isn't traditional conservatism, it isn't traditional republicanism, it is authoritarianism. But I think a better word for it, gangsterism... We don't have Ronald Reagan anymore. We have Tony Soprano.” According to MEAWW, Conway went on to criticize Trump’s alleged intimidation tactics and his willingness to “threaten and to assert power over things.”
Conway’s personal opposition to Trump is longstanding and well-documented. His critiques began during Trump’s first term, when Conway’s then-wife, Kellyanne Conway, served as a senior counselor in the White House. Over the years, Conway has used his platform to challenge Trump’s actions and rhetoric, often with biting humor and legal analysis. His decision to wear an “I am Antifa” shirt at the rally was seen by some as a symbolic embrace of the broader anti-Trump resistance, while others viewed it as a provocative gesture that risked further inflaming political divisions.
The backdrop to Conway’s protest was a dramatic escalation in the Trump administration’s response to left-wing activism. In September 2025, following the politically motivated murder of Turning Point USA founder Charlie Kirk, President Trump signed an executive order designating Antifa as a domestic terrorist organization. The order instructed federal agencies to “utilize all applicable authorities to investigate, disrupt, and dismantle any and all illegal operations” associated with Antifa. The Daily Caller reported that the FBI had launched investigations into possible connections between leftist groups and Kirk’s killing, and that the Department of Justice had brought its first federal terrorism case against two individuals allegedly tied to Antifa ideology. Prosecutors claimed the suspects had coordinated a July attack on a Texas federal immigration detention facility, marking a new phase in the government’s crackdown on radical activism.
The Trump administration’s aggressive posture toward Antifa and similar groups has been a source of intense political debate. Supporters of the crackdown argue that decisive action is necessary to prevent politically motivated violence and to uphold public order. Critics, however, contend that the administration’s rhetoric and policies risk conflating peaceful protest with criminal activity, and could be used to suppress legitimate dissent. The “No Kings” rally, with its mix of peaceful demonstrators and more radical elements, became a microcosm of this broader national conflict.
Conway’s role in the day’s events did not go unnoticed by political commentators. Some on the right mocked his apparent transformation from Republican legal mind to left-wing protester. Benny Johnson, a conservative media personality, tweeted, “President Trump has officially broken TDS victim George Conway.” Others saw Conway’s actions as emblematic of the growing willingness among some former conservatives to join forces with progressive activists in opposing Trump’s agenda.
In the days following the rally, Conway continued to use social media as a platform for his critiques. On October 10, for example, he questioned the official narrative surrounding Trump’s “routine physical” at Walter Reed National Military Medical Center, zeroing in on the mention of “advanced imaging” in the president’s physician’s statement. “'Advanced imaging' are the important words here,” Conway wrote, suggesting there was more to the story than met the eye. According to MEAWW, this was just the latest in a series of pointed public remarks from Conway, who has compared Trump’s leadership style to that of a mob boss and accused him of bullying and intimidation.
As the dust settles from the “No Kings” rally, one thing is clear: the divisions that define American politics in 2025 show no signs of fading. Conway’s appearance in an “I am Antifa” shirt at a protest against Trump’s administration was both a personal statement and a reflection of the broader tensions roiling the nation. Whether seen as an act of solidarity or provocation, it has sparked conversations about protest, power, and the future of dissent in the United States.
