The City of Boston has filed suit against Transportation Secretary Sean Duffy and the Trump administration over the cancellation of a $20 million federal infrastructure grant, arguing the withdrawal was unlawful, overtly political, and contradicted the explicit purpose of the programme Congress created. The case, City of Boston v Duffy, was filed in the US District Court for the District of Massachusetts. The grant, awarded under Biden's Rebuilding American Infrastructure with Sustainability and Equity (Raise) programme, funded the Roxbury Resilient Corridors project — safety improvements, public transport upgrades, accessibility enhancements, and traffic flow fixes across three streets that rank in the top 3% of Boston's streets for traffic injuries and fatalities. The area is classified by the transportation department itself as one of "persistent poverty" and a "historically disadvantaged community." The Department of Transportation gave a single reason for rescinding the grant: the project included electric vehicle charging infrastructure. Boston contends that component accounted for less than 1% of the project's total cost. The entire $20 million allocation was killed over a line item so small it rounds to a rounding error. The legal argument is straightforward and consequential. Congress established the Raise programme with specific statutory purposes — promoting sustainability, safety, and technological innovation in underserved communities. The lawsuit argues federal agencies cannot retroactively rewrite programme criteria to reflect a new administration's political preferences. If the transportation department can cancel a grant because it dislikes one congressionally-authorised element worth a fraction of a percent, the mechanism becomes a tool for ideological vetoes over any federal spending. Mayor Michelle Wu framed the fight as both local and systemic: "Boston earned this competitive grant to meet community needs and address long-needed infrastructure upgrades." Congresswoman Ayanna Pressley, whose district includes Roxbury, called the cancellation evidence of "Sean Duffy and Donald Trump's contempt for the people we serve." The Public Rights Project, providing pro bono counsel, noted the absurdity of the ratio — a $20 million grant killed over EV chargers representing "a fraction of 1% of the funding." This is Boston's ninth lawsuit against the Trump administration, eight filed in partnership with the Public Rights Project. It joins a growing wave of litigation from cities including Chicago, New York, and Los Angeles challenging federal funding decisions since Trump returned to office. The pattern is clear: federal grant programmes are being weaponised as political leverage, with cancellations targeting ideologically disfavoured components regardless of their share of total project cost. The 20-year question is whether competitive federal grants survive as a functional infrastructure mechanism or become loyalty tests. If administrations can cancel awards over de minimis components they dislike, rational cities will either self-censor applications to avoid political tripwires or stop applying altogether. Either outcome degrades the infrastructure pipeline Congress intended to build.