Criminal Histories of Leaders Protesting Trump’s Crime Policies
Three leaders from groups opposing President Donald Trump’s initiatives to tackle violent crime in Washington, D.C., have histories of criminal convictions in the city.
Darrell Gaston, a member of the Free DC Advisory Committee, has been sentenced to community service in two separate cases involving violence and threats over the last nine years. The group’s executive director, Keya Chatterjee, and campaign director, Alex Dodds, have misdemeanors on their records, which were dismissed after they paid bonds, according to court documents. Recently, Free DC organized a protest downtown, encouraging residents to respond to Trump’s law enforcement policies by being “visible,” “speaking loud,” or even creating noise with pots and pans.
Court records indicate that Gaston, a former local politician, faced accusations in 2016 of a simple assault and making threats, eventually pleading guilty to the latter and receiving time served through D.C.’s deferred sentence program. In 2018, he was involved in another simple assault case, again leading to community service after a guilty plea.
Moreover, Gaston was named in a civil harassment lawsuit in 2012 related to an attempted break-in, while another individual accused him of threatening violence during a dispute. Both cases resulted in temporary restraining orders against him, but these were ultimately dismissed after the plaintiffs ceased pursuing the matters.
Meanwhile, Dodds has faced multiple charges involving crowding and obstruction between July 2018 and July 2025. Some of these cases are still ongoing, and the first incidents were classified as “post and confiscated.” In a post from 2021, it was noted that Dodds was previously arrested while protesting Brett Kavanaugh’s Supreme Court nomination in 2018.
Chatterjee has two similar charges of illegal gatherings or disorderly conduct recorded since 2016.
Requests for comment from Free DC, Gaston, Chatterjee, and Dodds went unanswered.
Notably, Free DC operates as a special project through two nonprofits that receive funding from significant left-wing organizations, including George Soros’ Open Society Foundations and The Tides Foundation, as previously reported.
In response to rising crime, Trump has deployed the National Guard and additional federal law enforcement in D.C. following violent incidents linked to governmental staff. Recently, Attorney General Pam Bondi initiated a federal takeover of D.C.’s Metropolitan Police Department.
A White House spokesperson emphasized that federal law enforcement’s increased presence has already deterred crime, drug distribution, and the use of stolen firearms. The spokesperson asserted that Trump’s decisive actions are aimed at restoring safety and beauty to the capital, highlighting their popularity among the public.
Contrastingly, Free DC positions itself as a champion of “racial justice,” opposing perceived attempts to militarize schools and communities. The group traces its political origins to former D.C. Mayor Marion Barry.
A gathering of protesters, including those holding “Free DC” signs, assembled Monday night in response to Trump’s crime policies, markedly near the site of a recent violent incident.
